Help I Sexted My Boss artwork

Help We’ve Gone Back To School | And William’s Shameful Secret

Genre

Comedy and Entertainment

Released

In this school-themed episode of Help I Sexted My Boss, William and Jordan swap stories about their very different school experiences, covering everything from uniform rules and school dinners to Saturday school, forging parents' signatures, and William's shameful secret of never making prefect. They also tackle a selection of school-related listener dilemmas, including a teenage crush, a superglue stain on school trousers, and a mother's knickers turning up in her son's lunchbox.

Topics school uniform rules, boarding school life, teenage crush advice, forging parents' signatures, school dinners memories, prefect badge history, embarrassing school moments

Mentioned in this episode Jamie Oliver

Chapters

  1. 0:02:06 Intro: Back to School Special
  2. 0:03:01 School Uniforms and Memories
  3. 0:28:37 William's Shameful Secret Exposed
  4. 0:36:46 Etymology: Prefect Badges
  5. 0:39:52 Listener Dilemmas: School Edition

Partner with Help I Sexted My Boss

Help I Sexted My Boss is produced by Audio Always. We work with brands on sponsorship, advertising and partnerships across our network of podcasts, reaching engaged listeners and viewers.

Advertising categories Children's Clothing, Birthday, Dating, Gifts And Greetings Cards, Homework And Study

Show notes

It’s time to iron the white shirts and dust off the silk ties – William and Jordan are going back to school! The boys discuss how long a school tie should be, going to Saturday school, and why Jordan had to regularly forge his mum’s signature. There’s also a selection of school-based dilemmas to assist with, including having a crush at 16, and how to get a dodgy looking stain out of the crotch area.

Want MORE Help I Sexted My Boss?:

https://sextedmyboss.komi.io/

If you want to get involved you can email us. You can follow us and DM on Instagram and TikTok, and watch the latest episode every Tuesday and Friday on YouTube.


Hosted on Acast. See acast.com/privacy for more information.

Full transcript

Jordan 0:02:06 Hello and welcome to Help I Sexted My Boss, the podcast where we help you navigate the challenges of modern-day life, answering your 21st century questions and finding solutions to everyday dilemmas like, can you tell a posh bloke off for themselves in a restaurant? Or what should you do if what you thought was a shark was actually man porridge? And of course, what should you do if you've accidentally sexted your boss? But we're not your usual agony aunts, are we, William Hanson, the UK's leading etiquette expert?

William 0:02:44 No, we're not, Jordan North, Capital Radio presenter. I'm more A-star pupil, you're more 5-star criminal. And that's from Ben.

Jordan 0:02:51 They're getting worse, these.

William 0:02:52 Not producer Ben. But at least if you're going to be a criminal, be a 5-star criminal.

Jordan 0:02:57 That's true.

William 0:02:58 None of you are like, 4-star. Criminal, 5-star.

Jordan 0:03:01 Before we do our toast today, we've got to say me and William are in our school uniforms.

William 0:03:06 Yeah.

Jordan 0:03:06 We're dressed as schoolboys, which I don't know, I feel like too—

William 0:03:11 It's unusual for you.

Jordan 0:03:12 Lopes in their late 30s. Are we in our late 30s now?

William 0:03:14 Well, I definitely now am, yes. You're normally dressed as a schoolgirl.

Jordan 0:03:18 Yeah.

William 0:03:19 So it makes a change for you to be a schoolboy.

Jordan 0:03:21 I don't know how I feel about it, but yeah, we're doing like a school special because Um, everyone's back to school this week. Yeah, I wanted to do it last week, but because William's posh and from a posh school, he was saying his school doesn't technically go back to the— I looked up my term dates for my alma mater.

William 0:03:38 You were like— What?

Jordan 0:03:40 You were like all the officers' kids at school. They all used to like have 10 weeks school holidays. We had 9. Start a bit later. And you're messing that up.

William 0:03:48 Sorry.

Jordan 0:03:49 So we're doing like, um, all things back to school today, as well as the usual bits as well.

William 0:03:53 Sometimes it's good to go back to school, back to basics, regress.

Jordan 0:03:58 Yeah. I've got the fat tie. That meant you was cool. Did it? Yeah. All Year 11s had this fat tie. You know, you had your fat tie and then you tucked the rest underneath.

William 0:04:06 Were you not told off?

Jordan 0:04:07 Yeah. You're like, you'd do it for like the start of the school. You'd walk in with it. And then as soon as, as soon as a teacher spotted you, they'd be like, oi, tie! And it had to be down to, I think it was 4 or 5 buttons. God, Teachers—

William 0:04:19 Surely it should start where your trousers— stop where your trousers start.

Jordan 0:04:22 Teachers hated where your top buttons were undone as well. You said top button.

William 0:04:26 Right, well, there's yours. Oh gosh, I have made such a mess.

Jordan 0:04:28 And I've got long sleeves here, but I weren't allowed long sleeves at school.

William 0:04:31 Were you in a short sleeve shirt?

Jordan 0:04:32 Yeah, my mum said she, she won't buy me long sleeves because she said they're hard to wash. So we had to have, we had to have longs, and I was like one of only Year 11s that had long sleeves because all lads had them rolled up like this. That was cool, and all girls thought were fit. So, I had short sleeves like I worked for NASA, you know, in the '60s. I had all these short sleeves and like pencil ties. So, my mum's like, I'm not getting you long sleeves. They get manky. They get mucky. They're hard to wash.

William 0:04:56 She needs Marseille soap if she needs to get the stains off. Today's toast is from Charlotte and Winnie the dog. It goes to Zoe and Chris. And Charlotte and Winnie say, can I please get a toast to my friends Zoe and Chris who are getting married at the end of September? They are the most amazing, funniest, and caring people I have the pleasure of knowing, and they both deserve all the good things in the world. Plus, they were the people who introduced me to your podcast, and I've been a dedicated listener ever since. Well, Zoe and Chris, have a lovely wedding day. This is to you.

Jordan 0:05:23 To Zoe and Chris.

William 0:05:25 I hope it goes all without a hitch.

Jordan 0:05:29 Oh, that's good.

William 0:05:30 Lovely.

Jordan 0:05:30 Before we get on to all things back to school, how was your birthday?

William 0:05:34 I had a lovely birthday, thank you very much. Good. Got the windows done inside and out, back and front. Yes. That was my birthday present. That just coincidentally was the day that the window cleaner could come. So, that's nice. They got the bird poo off my skylight, because last time I had the windows cleaned, literally the day later, a bird with diarrhoea on both skylights. Lovely.

Jordan 0:05:55 I don't think a bird with diarrhoea. I think birds just generally have loose stools anyway.

William 0:06:00 You want to have a look at what my skylights look like?

Jordan 0:06:02 I think birds genuinely, just to piss us off, shit on the worst possible place. They never shit on the wall. Or they have a shit on the roof.

William 0:06:10 Or go to the loo. Like, find a loo.

Jordan 0:06:11 Yeah. Like, little bird, they shit on your car, they shit on your windscreen, they shit on your doors, they shit on your windows, they shit on your skylight. Yeah. Pigeons especially. They know what they're doing.

Speaker E 0:06:22 Have you ever been shat on, Hi Guys?

Jordan 0:06:24 Yeah, I have actually. I got shat on.

Speaker E 0:06:27 By a bird or someone else?

Jordan 0:06:29 By a bird.

William 0:06:32 What would you do if a bird shat on your windscreen? break up with her. That's very good.

Jordan 0:06:38 William's Jolly Joker though, ain't it?

William 0:06:40 No, that's Paul Surgeon's, I believe.

Speaker E 0:06:41 That's not very 2026.

Jordan 0:06:43 Yeah, well, I know, I always watch it. I know, and I'm not like, you know, I don't know what the word is, but sometimes I watch Fools and Horses, you know. I watch it every Saturday afternoon if I'm free. So, you got yourself a new bird, Rodders? And part of me is like, oh, won't get away with that now. But my dad still says it. Yeah, he's got a new bird. Anyway, yeah, so you had a good birthday. Did my card arrive?

William 0:07:04 It did. Well, yes, your card and indeed assorted presents. You're very generous. So, let me tell you what happened. My parents were over. In fact, I should just say, dressed in my school uniform, leaving the house today with my parents in the house was weird. It was a bit of a brain thing for them. They came down and they got to see the weirdest thing. Hang on a second.

Jordan 0:07:20 You didn't get on the Tube like that, did you?

William 0:07:22 Yeah.

Jordan 0:07:23 Are you fucking joking?

William 0:07:24 Yes. And the train terminated at Paddington, so I've had to walk through mainline Paddington, because there was a problem with the Elizabeth Line, His Majesty's Elizabeth Line. And so I had to, yeah.

Jordan 0:07:33 Can I just say, as a man in his late 30s— Yeah. You know, slightly ugly. I don't think you should be going out in public dressed as a schoolboy.

William 0:07:44 I'm not dressed as a schoolboy. Well, no, but my school uniform— let's describe our school uniforms.

Jordan 0:07:49 You're dressed as a schoolboy.

William 0:07:50 So, I am in a navy blazer, which is not my school blazer. This one's bespoke. I'm in a white shirt, just a white shirt. I am in my silk reproduction school tie that I had sent off to have our polyester school ties, house ties, reproduced in silk. It's a bit frayed at the edge because it's many years old, and I'm just in grey slacks with a shoe. It has a whiff of schoolboy, but it—

Jordan 0:08:15 Can we stop saying schoolboy? It's freaking me out.

William 0:08:18 You're the one who said it.

Jordan 0:08:20 Yeah, don't go dressed in public. Anyway, your mum and dad were with you today.

William 0:08:24 Yeah, so when I came downstairs and they sort of looked at me and went, this is weird.

Speaker E 0:08:27 Did they take a picture of you on the front step?

William 0:08:29 No, I did— I did— I did— I'm gonna ask, should we have a photo of me with my little satchel? First day at school.

Speaker E 0:08:36 Can you do that when you get home?

William 0:08:37 No.

Speaker E 0:08:38 Please?

William 0:08:38 No, because I don't want my front door taken a photo of. I can come and do it with your front door. Well, do it in front of my front door. I'm not coming to your front door. Your back door. Just choose—

Jordan 0:08:46 You don't have one, do you? You live in Hackney.

Speaker E 0:08:48 Yeah, I don't. Just choose a random front door. Just walk down the street. That's unfair.

William 0:08:53 On whoever's front door it is.

Jordan 0:08:55 Anyway, so they were there, and the presents arrived.

William 0:08:58 Yes. So, doorbell goes, and it was His Majesty's Royal Mail. And in comes— and it was a big, big envelope that said Moonpig. And I went, right, well, I know who this is from. Opened it, and it was a big thing of chocolate. No note. I went, well, it's Moonpig, and there's no note. I know who this is from. So I thought, oh, that's nice, he sent something. Lovely. Half an hour later, different branch of His Majesty's Royal Mail, then comes a big envelope with a card, which is here. It's a lovely big, massive card.

Jordan 0:09:32 Very classy, I must say.

William 0:09:34 I always say the bigger the card, the more common. But this is lovely.

Jordan 0:09:38 Excuse me, that's a Wendy North special! Every birthday—

William 0:09:42 And there is Wendy North. There's me as Wendy North, long ago.

Jordan 0:09:44 Can I just say, this is what my mum does every birthday and Christmas. She sends a Moonpig with pictures on us. that usually she's got from the family WhatsApp group, and she does the largest one. I think it's very lovely and classy.

William 0:09:55 Well, you've picked some lovely pictures. You've got you and me backstage having our makeup done on tour, you and me dressed as different Kylies— gorgeous photo— me dressed as your mother, and me with a Domino's pizza sitting on a bed in Sheffield.

Jordan 0:10:06 Yeah.

William 0:10:07 And then inside is you, your sort of thirst trap at the gym.

Jordan 0:10:11 That's your favourite picture of me, so I thought I'd put you in there.

William 0:10:14 It's not necessarily my favourite picture, it's the one I laugh at the most.

Jordan 0:10:19 I think this is a cool classic card.

William 0:10:21 To William— beautiful handwriting— to William, wishing you a very happy birthday. Hope you have a great day and get lots and lots of presents, but most importantly, lots and lots of attention. Love you to bits, Jordan. Kiss kiss. Which is very nice, so thank you. And then half an hour later, door goes again.

Jordan 0:10:37 Yeah. There's a box of Moonpig flowers.

William 0:10:39 Now Moonpig, I don't want to tell you how to run your business, but why can you not send them all together?

Jordan 0:10:43 I was iffy about this. How are the flowers? Because usually if you send in flowers— I've never done it with Moonpig before, but I thought, this is what I'll do. I'll send them with Moonpig, see how it goes, because if there's anyone that's gonna be honest, it'll be you. Were they any good? 'Cause the picture looked great.

William 0:10:57 Well, I've arranged them now.

Jordan 0:10:58 Okay.

William 0:10:59 I've put them in a nice vase.

Jordan 0:11:01 Yeah. Be honest. Would you— could I send them again to other people?

William 0:11:06 Yes.

Jordan 0:11:09 Okay.

William 0:11:09 Your mum would love them.

Jordan 0:11:11 What's that meant to mean?

William 0:11:13 No, no, 'cause they're nice. There are so many of them. They're like whites and sort of off-whites and gerberas. Love them. So no, I think I'd go for it. Okay.

Jordan 0:11:23 All right.

William 0:11:23 I think they're nice.

Jordan 0:11:24 We'll have to get a few.

William 0:11:25 And it was lovely to receive your stems on my birthday.

Jordan 0:11:28 Fair enough.

William 0:11:28 So, thank you. Speaking of birthdays, I actually have a gift for you, as well as you giving me a gift. I was meant to bring this in last week, but I forgot. This is a digital meat probe thermometer, so that you never need to use that glass thing that's broken and that is manual. I had that for my chicken last night, actually. I'm not convinced it works, darling. Thank you. So, this is the best-rated one on the internet.

Jordan 0:11:53 Right.

William 0:11:55 And you stick it in the meat.

Jordan 0:11:56 Should we check it out? Ben, bend over.

William 0:11:59 Oh, that's a very sharp point.

Jordan 0:12:01 All right, thank you. Pleasure. That's great. That'll be really— that'll come in handy.

William 0:12:05 It wasn't that expensive, but I do think you need a reliable meat thing.

Jordan 0:12:09 Got to be.

William 0:12:09 Especially for chicken.

Jordan 0:12:10 Thank you.

William 0:12:11 Beef, you can get away with it being a bit underdone, but for chicken— I want it to be.

Jordan 0:12:15 I had a medium-rare burger in Spain. It was great. We can't get them here. You're not allowed, are you?

William 0:12:19 It depends if— and I always ask when I'm ordering burgers, I go, am I allowed to ask if it's— can I have it medium? And if they say, oh no, it has to be medium to well done, that means they didn't make the burger on site.

Jordan 0:12:31 Ah, okay.

William 0:12:33 So, you wouldn't want it anyway.

Jordan 0:12:34 Did you ever, when you had your birthday, did that always mean you were in school, or were you still on summer holidays?

William 0:12:40 No, I was always on summer holidays. Just, it was just at the end. So, you'd have my birthday, we'd celebrate that with my friends, do the pasta-making class that we did one year, then we would go back to school.

Jordan 0:12:50 That's lucky because that meant you avoided birthday beatings.

William 0:12:53 Well, not necessarily. Remember?

Jordan 0:12:57 Oh, they'd dead— you'd just go home with 2 dead arms because if it were like your 13th birthday, you got 13 digs.

William 0:13:03 Because you were 14th of February, so yeah, that's always in term time.

Jordan 0:13:06 Sometimes it was half term, but sometimes term time, and you'd never— when I was When I was at school, you'd never tell anyone it was your birthday because if people knew your birthday, you— I know people that got egged and floured on their birthday.

Speaker E 0:13:17 There was a bad one for me one year where I think I'd broken up with one of my girlfriends and it's— One of them, man.

Jordan 0:13:24 What were you at school?

William 0:13:25 Player.

Jordan 0:13:25 Casanova.

Speaker E 0:13:26 What can I say? And you were how old? This is so weird. I'll go back to that story, but I bumped into one of my ex-girlfriends in the cafe downstairs the other week. She was in the area to pick up her wedding ring.

William 0:13:38 Wow. It could have been me. It could have been me.

Speaker E 0:13:41 Um, but there was one birthday in particular where I think in the aftermath of this sort of fairly significant moment in the friendship group that I, like, innocently had been like, this isn't right for me. I'm on to the next one. I got a particularly bad round of birthday beatings.

Jordan 0:13:57 That's not nice. Yeah. Did you have that at your school?

William 0:14:00 No.

Jordan 0:14:00 No?

William 0:14:01 No one. No one got beaten.

Jordan 0:14:03 Talk to me, because we've talked about it now and then, but tell me about William Hanson at school. Did you have a nickname? What was your nickname?

William 0:14:10 Yeah, I had a— well, I think we said this before. I was Bacon.

Jordan 0:14:15 Yes. Why was that again?

William 0:14:16 Because Adam, my friend, basically, we were talking about breakfast the next day, and instead of saying William, he had obviously breakfast on the mind and said, are you going to breakfast tomorrow, Bacon?

Jordan 0:14:24 Yeah.

William 0:14:25 And then my brother's nickname was Egg. So, we were Bacon and Egg.

Jordan 0:14:27 Great.

William 0:14:28 And then my parents became known as Chips and Beans.

Jordan 0:14:31 Yeah, public school humour. Yeah, very much.

William 0:14:33 But my brother is still referred to as Egg by certain friends. Only really Adam now still calls me Bacon.

Jordan 0:14:41 Okay.

Speaker E 0:14:41 I didn't know about Chips and Beans.

William 0:14:43 Did you not? No. No, Bacon, Egg, Chips and Beans.

Jordan 0:14:45 A couple more questions as we're back to school and people—

William 0:14:47 Did you have a nickname at school?

Jordan 0:14:49 Yes, it was Dingle.

William 0:14:50 Oh, yes, yes, yes.

Jordan 0:14:51 Burnley. What was your bag and what was your pencil case?

William 0:14:55 I did have a briefcase at the end of prep school.

Jordan 0:14:57 You were literally Will from The Inbetweeners, right?

William 0:15:00 Yeah. Briefly. But then after that, I mean, I think I did have a rucksack, but then I don't know then what I had.

Jordan 0:15:06 All the Year 7s looked like tortoises, didn't they? Turtles.

William 0:15:10 Turtles, yeah.

Jordan 0:15:11 And their blazers too. Did you not have a Pepsi Max pencil case? I had that. I had that for 2 years, and it was—

William 0:15:17 I think I had a Smythson one.

Jordan 0:15:18 You didn't have a Smythson pencil case. I think I did. What was that, about a grand?

William 0:15:22 No, don't be stupid.

Jordan 0:15:23 Smythson. Did you— So I had a pull-string bag. Do you remember? So yeah, this is what we had.

William 0:15:28 That was our PE bag when we were—

Jordan 0:15:29 No, no, no, no. So you had your pull-string bag for your books, which is like a Nike or Adidas one. Then you had a JD pull-string bag for your PE kit that went over one shoulder, and you were cool. This was like 2005, '06. You were cool. I've got some pictures of me in school, actually. I'll, I'll, we'll get them up on the carousel.

Speaker E 0:15:46 Ours was always go to WHSmith and like pray for your, for your mum to get you a new pencil case. Yeah, sometimes you'd get given one, often you wouldn't.

Jordan 0:15:55 Did you fancy any teachers?

William 0:15:56 No, actually.

Jordan 0:15:57 No, I didn't either. No. No. What? No, I didn't fancy any teachers. Everyone fancied, everyone fancied Miss Crank. In fact, I think my dad did at— What was said? I think my mum and dad had an argument at parents' evening, 'cause I remember getting in the car and me dad weren't even bothered, hated parents' evening, and he went, she were all right, that Miss Crank. And my mum went, what's that meant to mean? I noticed that most chat, you've been in all of them.

William 0:16:24 Well, and for those of us, we didn't know Miss Crank, describe Miss Crank.

Jordan 0:16:27 Oh, she was my favourite. What subjects? So I had 3 favourite teachers. I had Miss Crank, Miss Wilson, and my form tutor, Miss Scott.

William 0:16:37 Okay, but Miss Crank, how did she look?

Jordan 0:16:39 Miss Crank taught ICT.

William 0:16:40 Okay.

Jordan 0:16:41 Yeah. And look back now, she's actually—

Speaker E 0:16:43 And obviously you're so good with tech now.

Jordan 0:16:44 Yeah, look back now, she was probably really young, 'cause she's still there now.

William 0:16:48 Miss Crank taught you how to get Chrome onto your laptop.

Jordan 0:16:50 So, yeah.

Speaker E 0:16:52 Uh, that is a mad realisation. Like, obviously, like, I've got friends who are teachers and it's like, they were literally 21.

Jordan 0:16:59 Yeah, it's mad. They were like 20, and at the time you're fully well old. Miss Scott, bless her, our form tutor. Yeah, think of this, she had all the Norths in her class.

William 0:17:07 Wow.

Jordan 0:17:07 Yeah, so all my brothers and stuff. My mum, my mum, one of them that were in every other week. She used to come in and go, right, which one is it this time?

William 0:17:14 But describe Miss Crank. Why did, why did your dad fancy her?

Jordan 0:17:18 I don't know. I don't know.

William 0:17:20 How old, how old was Miss Crank roughly, do you think? I don't know, probably then late 20s, early 30s. Okay, so what now will be—

Jordan 0:17:27 I don't— yeah. I'm still speaking to her now. She was— I did a special— a series with her recently. She's great.

William 0:17:32 Aww.

Jordan 0:17:32 What was your—

William 0:17:33 And she was Miss Crank, not Mrs. Crank?

Jordan 0:17:35 Everyone was just Miss, even if it was— What? Even if it was Mrs. Wilson, you'd say Miss Wilson. Miss Scott. Oh, no. We just did in our school. It was just Miss. Very strange school.

William 0:17:43 Is it? No, no, no.

Jordan 0:17:44 Yeah.

William 0:17:45 No, we used the right honorifics.

Jordan 0:17:46 What was your favourite subject?

William 0:17:47 English.

Jordan 0:17:48 Yeah, mine too.

William 0:17:49 Yeah.

Jordan 0:17:49 And media studies?

William 0:17:50 We didn't do media studies. No, we did Latin.

Jordan 0:17:54 Um, did you have a planner, school planner that your mum had to sign every week?

William 0:17:57 No one had to sign it. We had the blue book and a prep, a homework diary, prep diary.

Jordan 0:18:02 Okay. Because my planner, and I'm not, even now, if I was a horrible person and wanted to get money off my parents, I can forge my mum's signature so good. Because obviously your planner would say when you had detentions and then you had to have it signed. So I just used to do me Oh, so she would never know. Yeah, so I just used to do my mum's signature myself.

William 0:18:21 And did she sign it Wendy with a Y or Wendy with an I?

Jordan 0:18:23 It was Wendy. It was just a W. I'm not going to give her a signature, okay? But yeah, I can still— Do you know what? I could probably still do my mum's signature. Go on, do it for me.

William 0:18:31 We won't show this. This is mad.

Jordan 0:18:33 I can still remember it. And I always remember how she did her Rs.

William 0:18:37 Oh, she has a little heart.

Jordan 0:18:38 A kiss. Did you ever have detention?

William 0:18:41 No.

Jordan 0:18:43 You ne— Oh my God! You never had— You know Katie, Frizzleton Katie? Yeah. Yeah, she had one detention in school and she still bugs her now. I hadn't.

William 0:18:52 I think I came close, but I didn't get one.

Jordan 0:18:53 I remember my dad taking me to Blockbuster because I didn't have a detention one week in school. So, as a reward, they took me to Blockbuster and I could get any film I wanted. Yeah. You never had any detentions?

William 0:19:05 No. No, we had a little sort of— How big was your planner?

Jordan 0:19:11 Like an A4? Oh, A4.

William 0:19:13 Oh no, ours was like, you know, the size of a passport basically. And it'd reach across a page and you'd write all your homework.

Speaker E 0:19:20 So how many times did you ever— yeah, you didn't have to get a signature.

William 0:19:23 One per term.

Speaker E 0:19:24 Did you ever have to write your parents' signature?

Jordan 0:19:27 Yeah, all the time.

William 0:19:28 No, I didn't at all. We had to— if I was then going to be off games, I either had to get an off games note from my parents or from the housemaster. Was that PA?

Speaker E 0:19:36 And you forged that. No, that was sport.

William 0:19:38 So, that P was like an academic subject, sport, and then everyone on— I think it was on Tuesdays, Thursdays, and Saturdays you did sport in the afternoon.

Jordan 0:19:46 And September, going back in P, was always cross-country, weren't it?

William 0:19:49 Well, we— yes, we did what were called the pens. The long pen, the medium pen, and the short pen. I hated it.

Jordan 0:19:55 I think I did it one year.

William 0:19:56 Yeah, but for some reason they were called pens. Only happened once a year. Hated it. Worst subject? French. Oh no, maths.

Speaker E 0:20:05 Oui, oui.

Jordan 0:20:07 I, yeah, I were rubbish at maths. Yeah, I was in bottom set and then I got bumped up for my GCSEs to set 4, which were much better, and then I had to go down again.

William 0:20:18 What was your—

Speaker E 0:20:19 You had 5 sets?

Jordan 0:20:20 Yeah, is that not normal?

Speaker E 0:20:22 We had 4.

Jordan 0:20:23 Oh, we had 5.

Speaker E 0:20:24 How many sets did you have?

William 0:20:26 Uh, for each— were you streamed per subject or just generally?

Jordan 0:20:30 Per subject.

William 0:20:31 Yeah, fine. Well, I was in Math Set 7, which was the bottom set, and then I went up to Set 6.

Jordan 0:20:36 Set 7! I was terrible. You sick bastard! I know.

Speaker E 0:20:39 But there can't have been that many people at your school. Set 7!

William 0:20:42 Yeah.

Jordan 0:20:43 Oh my god! I was in Set 5, and half of them are fucking in jail now! Set 7! Set 7, you absolute thiccup!

William 0:20:52 I was terrible. I went to Set 6.

Jordan 0:20:53 Sorry if anybody's in— I was in bottom sets, but I didn't expect that from you. Sorry.

William 0:20:58 I was in top set for everything else, but for— or second to top.

Jordan 0:21:01 Latterly. I was in Set 2 for English.

William 0:21:03 Were you? Very good. But yeah, no, maths Set 6 latterly. Science— the thing is, I can't remember. It's like when people say to you now, what did you get for your GCSEs? I literally cannot remember.

Jordan 0:21:15 Oh, I can.

William 0:21:16 Sorry to any— sorry to anyone doing their GCSEs now or about to do them. I know it's the most important thing in your life at the moment. Just when you're an adult, nobody cares.

Jordan 0:21:25 I got—

William 0:21:26 I'm just about to tell you that. Literally nobody cares.

Jordan 0:21:28 I got 2 Bs, mainly Cs. and then he—

William 0:21:32 I can't even remember.

Jordan 0:21:33 I think I hated myself being the knob that I was when I was 16. I just didn't fill in the second part of paper.

William 0:21:40 What?

Jordan 0:21:41 Yeah, I shouldn't have gone.

William 0:21:42 What was the school lunch like at yours?

Jordan 0:21:44 Um, at school, yeah, so we had— it depends. Some weeks you were first to go in dinner, and then others you had to wait around 20 minutes whilst the first lot went in, which was always annoying. So it depends what year you was in. Do you remember? So you'd be starving just waiting around in uh, in yard. Uh, but I loved dinners. I had them both buttered up. I had Julie on one side and Val on the other. I can still remember the names. And I'd go up to Julie and we had garlic bread, chips, and gravy. It's like a soft garlic bread. It was great. Why are you wishing my father— Um, and then we would, uh, eat it and then I'd go up and get seconds. Yeah, but yeah, it was all right. Sometimes get a jacket potato. And then Jamie Oliver came in and messed it up for everyone, didn't he?

William 0:22:25 I don't think he messed it up. I think he made it a lot better. He did. No, no.

Jordan 0:22:29 Turkey twizzlers never did me any harm. That's all I'm gonna say.

William 0:22:32 No, look at you now.

Jordan 0:22:32 Exactly. What about you? What were your dinners like?

William 0:22:35 Lunch? Well, we did have dinner because it was boarding school. We had lunch, breakfast, lunch, and dinner. And I can't remember what we had. I didn't love it. I often didn't go to lunch. What? No. What? Didn't really go to lunch.

Jordan 0:22:47 I'd go to breakfast.

William 0:22:48 Did you not have— you had breakfast. Yeah, no, we didn't do packed lunch. And then dinner, dinner was quite nice, you know, curries, cottage pie, that sort of thing.

Jordan 0:22:58 How posh were your schools?

William 0:23:00 Chicken kievs, as we now call them.

Jordan 0:23:01 What? You had chicken kievs?

William 0:23:03 Yeah, we had the catering department, so it was different.

Jordan 0:23:07 I remember once they served sausage and mash and it got around the school like wildfire. We were buzzing. They just, I think they had some sausages left over at end of term and made some smash and everyone was just like, they got sausage and mash. It was great.

William 0:23:20 And what was it, what was a day like? What was it, what time did you start? What time did you finish?

Jordan 0:23:24 I can't remember. I think it was, I think it was like 10 to 9, you had to be in for form, finish for 3.

William 0:23:29 But how, what was registration? When would you have registration? Form. Oh, form, that's what you called it.

Jordan 0:23:34 Yeah, I thought you meant you had to be in the class. You had to be in form for 10 to 9, that was 10 minutes. Or was that assembly? And then I think about 9, I actually can't remember. And then 9, but I remember you finished about I think we finished at 20 past 3.

William 0:23:46 Gosh.

Jordan 0:23:47 Yeah. What about you?

William 0:23:48 Period 8 by then. Uh, we had chapel at 8:30, which was the assembly, but that was the biggest thing. So we'd have a 20-minute service of prayer.

Jordan 0:23:57 Every morning you had to pray to God?

William 0:23:59 Yes. And then on Saturday we had Congas.

Jordan 0:24:02 Saturday?

William 0:24:03 Yes.

Jordan 0:24:03 Did you go to school on Saturdays?

William 0:24:04 Yes.

Jordan 0:24:05 What? Saturday? What time on Saturday?

William 0:24:08 Same times. In for Congas, which was congregational practice. shortened to Congers because public school.

Speaker E 0:24:13 You did the conger at school? No.

William 0:24:16 Oh, I wish we did. It would be more fun. Congers, C-O-N-G-E-R-S. So, you did hymn practice. So, you'd do 3 or 4 hymns, and you'd practice the hymns, and then you'd go into lessons. And then we'd finish Saturday school about 1, and then latterly, that's when I'd go home. Uh, or if you did sport, you then did sport.

Jordan 0:24:35 I'm so glad I was working class. Genuinely, I couldn't think of aught worse going to school on a Saturday.

William 0:24:42 And then we had, on then 3 Sundays a term, we had chapel on the Sunday. So, we had to go in again on a Sunday, and that was an hour.

Jordan 0:24:49 The only time we went to school on a Saturday was to climb the roof. That's mad.

William 0:24:55 But if— I think it's when you are a boarding school and you've got people, you know, international students, etc., and they are living away from home, you've basically got to do something with them. So, you thus just do Saturday school.

Jordan 0:25:04 What was your bell? Did your teachers go mad? The chapel bell. Did you go, that bell's for me, not you!

William 0:25:10 I think, yes, I have heard that before. But we would have— it was manually pulled by the verger every 15 minutes. What? Manually pulled the bell.

Jordan 0:25:19 You're joking.

William 0:25:20 And then on Saturday— on Sunday, when it was chapel, because bizarrely, the verger, Alan, who's a great friend, his day off was Sunday, which I always think is odd for a verger to have their day off as the Sabbath, which is great.

Jordan 0:25:33 Well, you can't be pulling bells every day of the week.

William 0:25:34 No, but that's the major church day, is a Sunday. They don't have that as a day off. So, you wouldn't pull your bells every 15 minutes? No, not every 15, every 40. You'd have a bell to say end of lesson, then you had 5 minutes to get to the next lesson, and then it would go again. And if you weren't then in your classroom by that second bell, that spelled trouble. But I was the virgin. I was a campanologist on a Sunday, so I would do the bell to announce that everyone had to walk to chapel. So, that was my job. Hey, would you do anything differently if you're doing school again now?

Jordan 0:26:02 Probably all of it.

William 0:26:03 Like what? Would you pay more attention or not?

Jordan 0:26:06 Probably do, maybe in maths, yeah.

William 0:26:09 Okay.

Jordan 0:26:10 What about you? Um, I did all right.

William 0:26:12 I'd just say no more often. Like when they're trying to make you do things, like the cross-country pens, I'd just go, no.

Jordan 0:26:18 Well, you had to. That sounds—

William 0:26:19 And actually, like detention. Okay, what, you're gonna put me in a room where I can just quietly get on with work? Lovely. I genuinely don't— I don't think that's a threat.

Jordan 0:26:27 We had isolation. That was even worse.

William 0:26:29 Even better!

Jordan 0:26:30 Did you have that?

William 0:26:31 No. Well, we might have done, but I didn't have it.

Jordan 0:26:33 I got put into— 'cause I was always detention, and I was a bit— how can I put this? I was a bit cheeky, right? And I once got put into isolation. That's where you got taken out of lessons.

William 0:26:42 And you sit in a room on your own?

Jordan 0:26:44 I walked into that, and that was like prison for me, and I thought, this ain't me, this. this— there was a lad with a cigarette behind his ear and a burst nose, and I thought, I'm not this naughty. And you know when that, that chubby guy at the start of Shawshank Redemption walks in and they're like, I'm gonna give him 5 minutes, and he starts crying? That were me. And I thought, I'm a bit bad, but I'm not this bad. And it were good for me. Isolation were horrible. It were a windowless room, a real strict teacher. They took it in shifts. and you had to be on a table on your own and you couldn't speak and you just had to like rewrite. Like, it meant you were so bad you got taken out of lessons.

William 0:27:23 Gosh.

Jordan 0:27:23 I got taken out of lesson, yeah.

William 0:27:25 Wow.

Jordan 0:27:26 Yeah, it was a wake-up call for me. I thought, I'm not with these reprobates. This is, this is different level of shitheadness, this.

William 0:27:33 Did you have anyone— we had someone called a marshal who was in charge of discipline and making sure our uniform was correct, and he's literally— he was an uh, army officer and his— he was a major and his— he had a separate office. And if you weren't in lessons or you had to go and see the marshal, you were told off by him.

Jordan 0:27:51 God, no. That was his job, to just bother kids. Yes.

William 0:27:54 And I remember thinking if, uh, whatever career— I mean, at school I didn't want to be an etiquette coach, even though I started being— I didn't know it was going to be a career. I thought I could be a school marshal. Continuing our school theme, uh, the team and I have been doing some investigating to put your deputy head girl debate to bed. Because you cannot remember who the deputy head girl was.

Jordan 0:28:11 Yes.

William 0:28:12 Do you want to, at this point, have one final guess at who it might have been?

Jordan 0:28:17 I honestly— I thought it was Jade Maroczan.

William 0:28:20 Jade Maroczan? Sounds like something you'd go into a B&Q shop and ask for.

Jordan 0:28:25 So, but yeah, I can't quite remember, and it's bugging me. Fraser Ewing. I think it was Fraser Ewing was our head boy. I'm pretty sure.

William 0:28:33 Okay, well—

Jordan 0:28:33 Bear in mind, this was 20 years ago when I left school. 2006.

William 0:28:37 Well, we have been in touch with Mrs. Crank.

Jordan 0:28:41 No way!

William 0:28:43 Really? And we've been exchanging emails. She's a delight. I've got a golden—

Jordan 0:28:47 Oh, she's great. She's great.

William 0:28:48 I've got a golden—

Speaker E 0:28:49 She's especially complimentary about your dad, weirdly. Thought it was a bit odd.

William 0:28:56 I've got a golden envelope, or goldenish envelope here. And inside is the name of your deputy head girl.

Jordan 0:29:02 Oh, thank God. I'll be able to sleep at last. Really. This has been bugging me, this.

William 0:29:07 It's a birthday card. It says, Birthday boy, it's your day. Dearest William, hope you have the best day. Love, Mrs. Crank. P.S., Jordan's deputy head girl was called— drumroll— Rebecca Lingford.

Jordan 0:29:22 Oh, shit! Yes! Of course it was Becky Lingford! Oh, that's gonna bug me! Now I can sleep. It was. So was Jade Vyse deputy head? It was Becky Linford.

William 0:29:36 It was Becky Linford.

Jordan 0:29:37 She was really, really good at sports. In fact, really good at sports. She was like shit hot at PE. She was the best triple jumper I've seen in my life, and I've been watching Olympics. Honest, Becky Linford, of course.

William 0:29:51 So Fraser Ewing? Fraser's a very posh name.

Jordan 0:29:54 He was quite posh, Fraser. Yeah, was it Fraser Ewing? I'm pretty sure it was. Was head boy. He was, Fraser was head boy. It's Scottish.

William 0:30:04 Scottish?

Jordan 0:30:04 Well, his dad was Scottish. He used to always wear a Scotland top. There you go.

William 0:30:07 Well, there we go. Well, thank you, Mr. Craig. Thank you for the card, and thank you for settling that debate.

Jordan 0:30:12 Well, I've been doing a bit of school research about you. Okay. And sending some messages behind your back. Yeah. And you think you're quite good at school, don't you?

William 0:30:21 Generally.

Jordan 0:30:22 Well, I have a message from someone who would beg to differ, really, Harrison. Okay. And they're telling us what you're really like Hello, Jordan.

James (William's brother) 0:30:31 Oh, it's my brother. Hello, William. James, William's brother here. Couple of stories I can share with you about William not being 100% squeaky clean during his school days. The first one, he was accused basically of vandalism, of breaking a light switch. Now, I think I'm right in saying he has denied it to this day.

William 0:30:53 Oh yes, I was young.

James (William's brother) 0:30:54 But I don't think it's ever been proven decisively one way or another. Then, when he was a lot older, he was an early adopter of the podcast. So long before Sex did. Yeah. He was doing a podcast with his friends George and Ashley, and as part of it, they would prank call senior members of the school or other bits of the school. And I can only assume that is why William was never made a school prefect, but I was.

Jordan 0:31:22 Ah, see, I had you down as a prefect.

William 0:31:25 No. No. Well, we'll get on to that in a minute. It's a little scab. I was in prep school, but not in upper school. Okay.

Speaker E 0:31:35 So, did you break the light switch?

William 0:31:36 So, the story goes— this was in my school before Clifton College, St. Brandon's. I was, I don't know, 5, 6. And the, you know, like, it was a cord light switch, one on the cord, and it had been— it had got wrapped around something, and so it was dark. So, I jumped up, to try to pull the light switch and pulled it down. And it thus— because I was, you know, obviously stronger than I looked and didn't really understand how corded light switches work, age 6— it just came out the ceiling. And I believe the headmistress came in— I won't say her name— and said, you deliberately pulled that down. I said, no, it was wrapped around. And so apparently— I can't remember this, but my mother does because my mother got a phone call. I deliberately broke the light switch. No, I was trying to do us all a favour because the changing room was in darkness, and I was trying to pull the light switch down. And my mother would never forgive that headmistress because I got told off quite unnecessarily, apparently. So, thank you, James, for reminding me of that. Um, should we do an Etymology on prefect badges?

Jordan 0:32:37 Oh yes, let's do that. Okay.

Speaker G 0:36:23 It's William, William, the etiquette geek. His knowledge, knowledge is quite unique. He'll give you manners Manners, manners. A subtle tweak. It's time for William's Etiquetti-Mettiquetti-Menology of the Week. Cha-cha-cha, cha-cha-cha, cha-cha-cha. Cha-cha-cha-cha-cha-cha-cha-cha-cha-cha-cha-cha-cha.

William 0:36:46 So, where do prefect badges come from? Well, the prefect system is very old. Were you a prefect?

Jordan 0:36:51 No, I was not.

William 0:36:52 Milk monitor?

Jordan 0:36:55 Free milk? Thatcher got rid of that in the '70s. We didn't have free milk.

William 0:37:00 No, you may not— you may have paid for it.

Jordan 0:37:01 I was overhead projector monitor in Year 6.

William 0:37:03 Of course. Fine.

Jordan 0:37:04 Yeah, but then I got banned from that for doing Vs to all assembly.

William 0:37:10 Well, quite right.

Jordan 0:37:11 To be fair, Adam Palmer dared me, and he still— and he were right. Goody-goody schwap.

William 0:37:18 So, the prefect system dates back to the 14th century, with the oldest boys in the schools given charge over the younger ones. But what about the badge itself? Well, this is a newer add-on, arriving alongside the rest of school uniforms in the early 20th century, sometimes in silver or bronze depending on the rank, sewn or pinned onto the blazer pocket on the wearer's left-hand side. One possible origin story for prefect badges is from the 1930s where an English grammar school needed a new badge for their Army Cadet Corps, but the Corps ended up using a different mandated badge instead, so the leftover design got handed down to the prefects instead. So, a symbol of academic seniority, at least in that case, started life as army surplus. It's a good reminder that a lot of school tradition isn't ancient wisdom handed down; it's just whatever was lying around and got repurposed and made official. So, there we go. Did you have a school song? I mean, you went to many schools. Did any of them have a school song? No. Did you not? We had an unofficial— we had— I mean, our school song was called— I mean, it's so ick— The Best School of All. Well, um, I know, the best school of all. It's not even a good song, but we had an unofficial one, Which was fun, which I'll see if I can remember.

Jordan 0:38:26 I'm just going to warn you now, it's going to be public school by humanists. So it's going to be not funny.

William 0:38:34 We want no more history. French is a crashing bore. Science should vanish and geography should be banished and maths thrown out the door. What a good idea. Classics are a mystery. Music, what a drag. And the teachers teach us nothing because they spend their time doing nothing. But nag, boom. I can still remember that. I have not sung that in 20 years.

Jordan 0:38:57 See, that was your humour. I got Bluetoothed someone being captured in Afghanistan in Year 10.

William 0:39:02 Right.

Jordan 0:39:03 And it's still— that image still haunts me to this day. No one should see that.

William 0:39:08 No, no, they should not.

Jordan 0:39:10 It's horrific. I still remember it.

Speaker E 0:39:12 Incredible that you can remember that.

William 0:39:13 Thank you. I was actually genuinely quite impressed with that.

Jordan 0:39:16 That was— that was a knack, right?

Speaker E 0:39:17 But also incredibly, incredibly awful lyrics. Yeah.

William 0:39:20 All right, well, what was your school song?

Speaker E 0:39:21 I don't have a school song. He didn't have— we went to normal—

Jordan 0:39:24 he's the most middle-class boy ever, and he even— he didn't have a school song.

William 0:39:27 Izzy? Jack? Sophia? No.

Jordan 0:39:31 Did you go to a Catholic school, Izzy? Of course. Were you taught by nuns?

Speaker H 0:39:35 No, we had a couple of priests, but no nuns.

Jordan 0:39:38 Now it's time for your questions and dilemmas. Remember, if you need our help with something, then get in touch. You can send your tales of trepidation to help@sexwithmyboss.com, or you can DM us. We're @sexwithmyboss on What have we got now then, please, Willy?

William 0:39:52 This is from anonymous. Hi, William Jordan, producer Ben. I'm writing to you today with a crush dilemma that I need significant help with. For context, I'm a 16-year-old boy in Year 11 about to sit my GCSEs. Remember, no one will ask you in 10 years. I have had a crush on this girl, let's call her Maddie, and we've been friends for a long time and get on really well. Back in April, I asked Maddie out and was rejected, as she said she didn't want to date in high school. I found that understandable and hoped I'd be able to move on from this crush I have had for about a year. Unfortunately, I still have a crush on Maddie several months later and don't know what to do. We've remained really good friends throughout the situation and still message on a regular basis several times a day. What is frustrating me is that so many of my friends constantly, constantly say that she is flirting with me, but I simply don't know what to do, and I'm giving the wrong impression as if I'm still trying to get with her when she's already rejected me. Any help would be much appreciated as I genuinely have no idea what to do. Thank you very much for reading my letter, as your podcast has helped me through some very dark times in my life, and with this podcast it has been a much needed break. I look forward to your response. Anonymous. Oh, bless you, Anonymous. Well, you know, there are plenty more Maddies out there, is what I'd say. Don't worry too much about it.

Jordan 0:41:06 You could try one more time and be like, look, what about when we finish school? Why wouldn't you want to date? I think, Anonymous, she'll maybe be impolite and say she doesn't want to date in school. So just try and move on. But trust me, you think Maddie will be the love of your life now in school?

William 0:41:21 You won't even remember Maddie.

Jordan 0:41:22 Yeah. You're talking to 2 old men here. Yeah, they were— they're telling you now, like, you think you're in love and it'll— yeah. You'll meet many more Maddies.

William 0:41:33 Who was your crush at 16? At school?

Jordan 0:41:36 Dunno. Who was yours?

William 0:41:40 I can't remember her name.

Jordan 0:41:41 Very good.

William 0:41:46 Matron, probably.

Jordan 0:41:47 Didn't you guys go on our bicycle?

William 0:41:49 No, sadly.

Jordan 0:41:50 Oh, was the girls outside?

William 0:41:51 Yeah, they let a few in. For balance.

Jordan 0:41:54 All right. Okay. Well, look, yeah, try not to— these— if she said no once, maybe it's time to take that and move on. Maybe one more time, but—

William 0:42:03 No, I'd move on.

Jordan 0:42:04 If after the second time, then absolutely don't pester her.

Speaker E 0:42:07 It can be quite all-consuming, a schoolboy crush, can't it?

Jordan 0:42:12 Yeah.

William 0:42:13 It's because— and I mean this with absolute respect. It's maybe because there isn't, other than lessons and sport or anything co-curricular that you're doing, there isn't an awful lot else to worry about. And so, thus it— but, you know, once you start having rent to pay and having to find a job, you'll move on very easily. This is from Dan. Hi, William and Jordan. My friends at school used to routinely put glue on my crotch without me looking. This resulted in having a very embarrassing-looking stain that was incredibly difficult to remove. I have 2 questions related to this. William, what is the best way to wash super glue out of school trousers? And Jordan, what would the perfect act of revenge be for this? I'm still friends with some of these degenerates, so revenge could still be achieved.

Jordan 0:42:50 Next time you're at pub, just go in, like, do you want a pint? And just go, ahh! And squirt superglue on them. Go, ahh, you got cum on your trousers.

William 0:42:58 That would be me.

Jordan 0:42:59 I would do the same thing now, 20 years later.

William 0:43:01 I'd use a PVA gun.

Jordan 0:43:02 I'm still gonna get Stuart Pilkington back.

William 0:43:04 I thought you were gonna say Stuart Malkin.

Jordan 0:43:06 He set me—

Speaker E 0:43:07 That is not a chairman emeritus Stuart. No. That's a different Stuart.

Jordan 0:43:11 He set me up big time in school, loads of times. I'm still getting— there's still quite a lot.

William 0:43:15 I, in terms of superglue onto trousers, I've never had to get superglue onto trousers. It also depends on the material of the trouser. But very similarly, over the weekend, I had to get candle wax off my candlestick. And so you pop it in— Don't twist that. I know, it dripped all down it.

Speaker E 0:43:33 Candle wax off your candlestick?

William 0:43:35 Candle wax. So the candle had melted and gone right down, and then the silver candlestick— it then gone all over the silver candlestick. Pop it in the—

Speaker E 0:43:43 Candlestick? Isn't it a candlestick holder?

William 0:43:46 You just call it a candlestick? Oh, yeah.

Jordan 0:43:49 That's what a candlestick is. Isn't that what the candle is? Yeah.

William 0:43:51 No, that's the candle and the candlestick.

Jordan 0:43:54 No, that's the candle holder. I thought you said candlestick.

Speaker E 0:43:56 No, it's a candlestick.

William 0:43:57 Could someone Google candlestick and see what comes up? Also, I mean, don't out-etiquette me.

Jordan 0:44:03 Anyway, carry on.

Speaker E 0:44:04 I just always thought that the candlestick meant the candle.

William 0:44:07 No, that's a stick. That's a— it's a candle that's sort of sticky.

Speaker E 0:44:11 It's a stick candle. It's a stick.

William 0:44:14 It's a candle. Well, let's pop this on our Instagram and see what people think. I think they'll agree more with me that you have the candle that goes in the candlestick or candelabra, depending on what— Anyway, same, same print. We've got distracted here. Ben, as ever, has made us pivot. I would pop your trousers into the freezer, and maybe the glue will then go sort of very, very, very hard, and then you can, like, with a credit card or with a spatula or something, try and scrape it That's what I'd do.

Jordan 0:44:43 Stuart Pilkington kicked chewing gum and it went in me eye. You know, I used to lob a chuddy. I had a big chunk. I'm still gonna get him back one day. I'm gonna put a big bit of chuddy in his eye.

William 0:44:54 Stephen Pake fired an elastic band in my eye.

Jordan 0:44:56 Oh.

William 0:44:57 It didn't quite hit the eye, but it hit underneath. That was not pleasant.

Jordan 0:45:01 That explains. Yeah. It's never quite gone away, has it?

William 0:45:06 I do have ptosis in one eye, yes.

Jordan 0:45:08 A ptosis?

William 0:45:09 A ptosis. P-T-O-S-I-S.

Jordan 0:45:12 What's that, like psoriasis?

William 0:45:13 No, a ptosis means where one eyelid is lower than the other.

Speaker E 0:45:18 I have that.

William 0:45:20 Do you? You and I are going to have to keep— we have to boom boom keep an eye on it because as you get older and your muscles weaken, as generally is what happens, if the eyelid then goes over the pupil— this is what I was told, medical people write in, please let us know if this is correct— If it goes over the pupil, basically the brain will then think that we don't need that eye and switch that eye off, and we go blind in one eye.

Speaker E 0:45:41 What?!

William 0:45:41 So I'm probably going to have to have an operation.

James (William's brother) 0:45:43 You know the anxieties this boy has. Please don't give him another one.

Jordan 0:45:47 He's got another one now. You know how anxious he is, bless him, and you've just given him another— look at him.

William 0:45:51 Oh, at your age, you're fine. I mean, I'm probably gonna have to have this operation.

Jordan 0:45:53 We're the first to take the piss out of him, but he is our friend. But now look at him. Now he's gonna be worried about going half blind. I don't know. Anyway, go on. You'll be right. You'll be cute, Blanche. You'll be like little Pugty Bear.

William 0:46:06 Oh, we can both wear our eyepatches. You can wear your little eyepatches.

Speaker E 0:46:09 I think I'm more Jack Sparrow.

William 0:46:11 Jack shit. This is from Lewis.

Jordan 0:46:13 Very good.

William 0:46:14 Dear William, Jordan, EPB, and the rest of the team, back in Year 8, I would regularly be able to get out of class by using the lavatory. One afternoon, I asked for a toilet pass and slowly walked to the toilet to get out of the classroom for 20 minutes. When I eventually arrived at the toilets, I was greeted by a student with his trousers and boxers down to his ankles, standing at one of the urinals. The toilets were quite cramped, so I had to delicately squeeze past his bare bottom just so I could use the stalls. Is it incorrect etiquette to use urinals like this? And if so, should I have said something? Many thanks, Lewis. Yeah, I mean, I don't use urinals, but I would say you don't take your entire pants and trousers down. It's a bit— I mean, if the boy was in year— oh, year 8. I guess you're still working out how life works. You probably think you drop everything, which is what you do when you're 4 and you go to the loo.

Jordan 0:46:59 I was gonna say, if you did that in my I remember someone had a shit in our school and he got called Poo Boy for the rest of his life. You go in pub now, you go, oh, it's Poo Boy. Poo Boy from Year 8. He had a shit in school and everyone used to like, you'd all go over and have a look.

William 0:47:12 Oh.

Jordan 0:47:13 I think it's on Inbetweeners as well. You'd all climb up and give each other a poo. You wouldn't have a poo in my school. So if that happened in mine, you would have had a terrible nickname. No, but I think, yeah, I mean, Poo Boy now got a very successful scaffolding business, by the way. Just to let you know. So who's laughing last? Yeah, he's got about 6 wagons.

William 0:47:32 Give it to Shantown, what's his name?

Jordan 0:47:33 I honestly couldn't tell you.

Speaker E 0:47:36 Is that what you call it, wagons?

Jordan 0:47:37 He's got about 6 scaffolding wagons. For me, you're just known poo boy. You were 2 years below me. I was in Year 11, I think you were in Year 9, and got caught having a shit. Ginger last.

Speaker E 0:47:47 It was all up from there.

William 0:47:48 But Lewis, yes, I would say you whip down your pants and your trousers when you're sitting on the lavatory. But if you're using a urinal, I believe you just sort of lower or unbutton your fly and then— Fair. What's-ma-call-it. This is from Angela. Hi boys, my son returned from school the other day looking rather sheepish. After much persuasion, he eventually told me to go and look in his lunchbox. I wasn't quite sure how to prepare for what I was going to find, and I started to fear the worst: a dead animal, a priceless piece of jewellery, a poo. Thankfully, it was none of them, as it was just in fact some of my knickers, It seems that in my haste, I recently washed his coat at the same time as some of my undergarments, and they had somehow worked their way into one of his coat pockets. The poor boy unknowingly whipped them out in front of all his friends in the playground and had to hide them in his lunchbox till he got home. How can I make it up to him and give some way to heal his embarrassment? I don't know how old your son is. I'm gonna say he's probably early teens. That's probably— because if you were like 8, I don't think you'd be that embarrassed.

Jordan 0:48:44 The best way you can make it up to him is just pretend it never happened. Don't keep bringing it up. Don't try and get him a present. He doesn't want to talk about it. He doesn't want to know about it. I'm speaking from experience because it happened when our Ryan put his rugby top on and my mum's— well, I'm not even gonna say panties— my mum's thong was stuck to the back of him, right? Don't forget, Wendy was in her, you know, she's only in her late 20s when our Ryan was in school.

Speaker E 0:49:05 She was in her prime.

Jordan 0:49:06 Yeah. Wow. And they didn't talk about it for years, and now they laugh about it.

William 0:49:11 I think you'll find Jordan, a lady is always in her prime.

Jordan 0:49:13 A lady is always in her prime. And now they laugh about it, but I'm not— it was a full-on thong, as far as I'm aware. It stuck to his back of his thigh. Easy to miss.

Speaker E 0:49:22 Easy to miss.

Jordan 0:49:22 I need textile rain. I think it was a thong. Anyway.

William 0:49:26 Yes. So, I would say buy him something nice.

Jordan 0:49:29 Yeah.

William 0:49:30 Yeah. Say, I'm really sorry. Also, top tip for future, regardless of whether you're washing with your school's clothes or not, underwear probably should be washed in a mesh bag. And then that'll stop that from happening as well. Just under— ladies' underwear. More delicate garments. Unless they were your big Spanx, in which case, you know, whatever. Anything goes. Well, thank you very much for all of those.

Jordan 0:49:52 There was— I remember skiddy as well. Honestly, we went swimming, and when he took his—

Speaker E 0:50:01 Yeah, we get it. We definitely get it.

Jordan 0:50:03 He had a big skiddy in him. Yeah. And I still— up until I deleted it, I followed Skiddy on Facebook for years. But I wonder what— Skiddy, if you're listening, let us know. I haven't heard— again, I couldn't even tell you.

Speaker E 0:50:14 So Skiddy Poo Boy, Rebecca Linford, if you're listening, get back in touch.

Jordan 0:50:20 But to be fair, Skiddy was at Carr Hill, so it was Year 8. Yeah. Anyway, thank you for your questions and dilemmas. Remember, you can listen to new episodes every Tuesday and Friday and 24 hours before anywhere else on player. If you want to get in touch about something that isn't a dilemma or a problem, drop into our DMs or send us an email to help@sexwithmyboss.com. We also love hearing back from the people we offer advice to, so if that's you, get back in touch and we'll see you on Friday. Goodbye. Bye-bye.

This transcript was generated automatically and may contain errors.

More from Help I Sexted My Boss

  • Jordan Is A Fruber?! | And How To Drop The Poo Bomb 18 September 2026In this Friday episode of Help I Sexted My Boss, William and Jordan discuss listener-invented rude paint colour names, then William fields quickfire etiquette questions on topics ranging from cappuccino froth to fridge magnets. The episode also features a letter revealing what "froobing" means, which threatens to ruin Jordan's beloved Frube habit for good.
  • Help We’re Getting Intimate | And William is Ainsley Harriott?! 15 September 2026In this episode of Help I Sexted My Boss, William and Jordan debate what counts as intimacy, with Jordan also admitting he has adopted William's sit-down weeing habit after previously mocking it. The pair answer listener dilemmas covering a husband watching pornography on X, public flossing etiquette, best man speech advice, sock-changing habits, and the correct way to tuck in a shirt.
  • The Sexted Exam | And School Rumours 11 September 2026In this episode of Help I Sexted My Boss, Jordan North and William Hanson attempt a Year 6 SATs-style quiz, testing their knowledge of science, geography, English and maths with the help of producer Ben. They also read out listeners' favourite school rumours and myths, and respond to messages including a medical voice note about a previous listener dilemma.
  • Has Jordan’s VOICE Changed?! | And Poppins Parody 4 September 2026In this episode of Help I Sexted My Boss, William and Jordan revisit archive clips from the early series to determine whether Jordan's voice and accent have changed over eight years. The episode also features a Mary Poppins parody clip, listener-suggested names for a Sexted hardware store, and a rebuttal from a self-described card-carrying Catholic disputing Jordan's claims about weak Catholic handshakes.
  • Help That’s Not My Man Porridge | And Spanish Ironing Boards 1 September 2026In this episode of Help I Sexted My Boss, William and Jordan catch up after their summer holidays, sharing stories from Chicago and Spain — including a near-miss with a hotel ironing board and a dirty martini mix-up. They tackle listener dilemmas on filming food in upmarket restaurants, the grey-versus-colour interior design debate, Freemason port-passing etiquette, and an anonymous listener's alarming discovery of unexpected "man porridge".
  • Jordan Loses His SH*T | And Wendi’s Coffee Table Books 28 August 2026In this episode of Help I Sexted My Boss, William and Jordan compete in a fiercely contested round of Guess the '90s Children's TV Theme, with Jordan losing his composure over the final result. The pair also attempt to match coffee tables to members of the Sexted inner circle, including Jordan's mum Wendi, before reading listener messages on topics ranging from corner shops to Disney villains.

All episodes and transcriptsAbout Help I Sexted My Boss