My Friends Most Embarrassing Stories!

At least once is our lifetime we all experience a moment of gut wrenching-want the world to swallow us up-embarrassment!! Usually at the most inconvenient times & places (hence the embarrassment)! They are always face palmingly cringe worthy, & without a doubt absolutely hilarious when it wasn’t us that it happened to!

Picture this – There I was nearing the end of my first year in secondary school, 12 years old, not even a teen yet! Having only recently started to mature as a young lady (by that I mean started my periods, those things I’d now have to endure once a month for the rest of my life, well until menopause!). It was a scary time for a young girl especially when most of my friends hadn’t begun yet! Luckily by the end of first year our form group had all clicked well and we always had a laugh in lessons (which was always funny until the laugh was on me). There we are in our first lesson of the day – Art. The jokers of the pack were seated behind me and my close friends, always in our proximity so we could chat without getting into trouble! Whilst us girls are in the middle of painting & gossiping about who we fancied the boys had quietly taken my school bag & started to rummage through it. All of a sudden all the boys started chuckling with laughter until slowly the whole room followed suit. I looked behind me to see a very proud looking smug lad (who I later went on to date & share my first kiss with!)my bag open in front of him, a bright green wrapped sanitary towel in his hand & my stash of them sprawled across the table!!! I was mortified! Absolutely horrified! Then the words from the same lad who’d been handling my toiletries says ‘Don’t worry its okay to bleed every month! Maybe you’ll need one for your face its so red!’ Followed by endless laughing & a very fragile me! They thought they had struck gold with that comment! Honestly as a 12 year old first year that moment engrained itself into my memory forever!

FYI – All of these hilarious moments really did happen! Most are anonymous to save further embarrassment!! These recollections are definitely not for the faint hearted so be cautious when continuing on!!!

1. When I was 11 I was in IKEA wearing my favourite blue skirt. The elastic pinged literally as I was walking and my skirt fell right to the floor. I was SO embarrassed. It was summer so no tights or anything, just me, in my knickers in the middle of IKEA!

2. Okay so I’m not one to act dumb just for the sake of it or to get attention, and that is probably what annoys and embarrasses me more than anything about this. People must have thought I really was playing dumb! So we were welcoming in a new year, watching the great view of the lit up city when people started to light up Chinese lanterns & let them go, it got me thinking… Where do all these lanterns end up!? So many people let them off there must be millions of them floating around out in space somewhere? Not very environmentally friendly!… I wish so bad now that it was me just thinking, but nope I actually said it aloud. My boyfriend couldn’t quite believe what I’d said and replied with ‘what are you talking about they deflate back down!? You thought they flew out to space!?’ Followed by continuous laugher. He literally told everyone we were with, it was awful! Our friends still tease me about that now. I’m now older and hopefully wiser!

3. I was getting ready to seduce my boyfriend when he got in from work, knowing he’d be back about 5. I started putting on a bit of lipstick and checking myself out in the mirror when I heard him come in from work, put his keys down and proceed to walk into the living area. I could hear him talking so assumed he was on his phone. I took my gown off, I was wearing only my best frenchies and one of his ties, popped my heels on and walked down the stairs, as I started approaching the living area I could hear another voice, not my boyfriends!! Shit!! My boyfriend must have a friend with him! So I try to back up very slowly. I really didn’t want to be heard or seen. Then my boyfriend shouts my name and says ‘we have company’ and as he says that they both walk round the corner, beers in hand and spot me!!!! Shocked we all just freeze and stand there for a second, which actually felt more like forever! I just ran, not knowing what else to do I shut myself in our room until an acceptable amount of time had passed. I later rejoined them, fully clothed and said nothing about what had just happened. I busied myself with cooking and drank ample amounts of wine!

4. I Got up at the end of my maths lesson, saw that I’d started my period because there was blood on my chair, my face went scarlett red! I tried to casually put my chair on the table & walk out towards the toilets! If my friends did see then they were kind to me & didn’t say anything! I was 14!

5. When I was pregnant I was round a friends house, I’d been there all day when I suddenly got really bad pains and thought something might be wrong with the baby! Long story short – I went to the loo to calm myself down, ended up doing a massive fart and was suddenly ok… I was so scared about farting near my mate I’d given myself those stomach pains! My partner was pissing himself laughing when I told him!

6. I was on a night out with some mates and my girlfriend at the time. The night got pretty wild quite quickly. There were some weird guys at this house party we ended up in, unusually loud and aggressive. Everyone at the party noticed something wasn’t right but we all continued to have a good time. One of the guys starts handing beers to everyone so me and my mate accept and took it as a token of peace. Half hour later I started to feel strange, sluggish, slurring my words, everything was moving slower in front of me. My other mates had either fallen to sleep or moved on elsewhere by this point so it was just me and my girlfriend. She noticed I was acting strange so thought we should walk it off and head home. I got onto the bus but by the time the journey was over I could hardly walk. My girlfriend had the pleasure of trying to carry me home from the bus stop which was uphill, as soon as we’d got inside I was sick everywhere & passed out. I woke the next morning to a unimpressed girlfriend, she understood though we found out my drink had been spiked. Thank God I’m not that much of a lightweight!

7. So I see a guy at a local bar and being an empowered woman I go up to him, buy him a beer and sultrily suggest “Your place or mine?” We get a cab to his where the obvious happens and we fall asleep. In the morning we go for round 2 and I think something feels a bit wrong – oh shit I’ve got my period! There’s blood all over the sheets and so he strips the bed – It’s on the mattress too. We head into the kitchen where he puts the sheets in the washing machine, we stand awkwardly as it pisses with rain outside, watching out of the window as a pigeon drowns on the flat roof. I swiftly leave but then 2 weeks later while at Thorpe Park who do I see guiding a group of children around??!!!! Then a month later his photo pops up on the projector screen showing pics taken at the bar. Two months after that, there he is on the DLR! To top it off over a year later I meet another guy – who was his flat mate. Aaaarghhh!!!!!

8. I went on a sports weekend with school in year 11. We were playing a game in the pool when my mate swam under to get me on his shoulders, he thought it would be funny to throw me backwards into the water for a laugh. As I surfaced the pool everyone started to point & laugh – I’d forgotten that my tankini top was too big! My boob only flopped out and everyone got a good eye full! Those who saw my bare boob spread around school that I have nipples the size of fruit pastels! That was my nickname for the week… fruit pastel!! Waaaah! Lol

9. I wanted to join my sister in her karate class – so I went along with her, we were stretching b4 the class started, good ole sit on the floor, legs in a v shape, stretching down to touch ur toes. The room was particularly silent… I ended up breaking that silence with a big loud fart!!!!! Yep everyone looked at me! That was the 1st & last karate class I attended!

10. Okay this is probably more embarrassing on the mans behalf than my own but here goes. I was at work on the tills, it was summer, around 4/5 so busier than the afternoon had been. I had a queue of people at my till when this older guy, in his 40s I’d say wanted to chat. So we are talking I’m asking about his day and he is divulging information that I’m not really interested in so I’m half tuning in and out. Then he goes ‘where from wales are you from?’ The lady behind him started to giggle and we gave each other an awkward look I looked at him and said ‘sorry did you say Wales?’, bare in mind I’m a Londoner born and bred! He suddenly goes a bit pink in the face and says rather slowly ‘yeeeeesss’, I had the embarrassment of having to tell him in front of all the customers who may I add were all listening, ‘I’m not from Wales, i’m from around here’, I didn’t want to make him look like a fool so felt super embarrassed myself! He didn’t say another word the whole transaction! Which made everything so tense!! Either that guy needs his hearing checked out or my accent is really off!! The lady behind him kindly told me after he eagerly took his shopping and headed out that I don’t sound welsh at all & we just couldn’t stop laughing!

11. 22 years ago, at the tender age of 22, a special friend announced she was getting married. All very quick (everyone assumed she was pregnant!), the wedding was organised at the local registry office. Suitable outfit was purchased, along with a really lovely wedding gift. Had no idea who future husband was as she’d met him on a night out and things had moved along really quickly, he wasn’t local either so nobody really knew him. I turned up to the wedding in my lovely new outfit with gift in hand. I didn’t automatically recognise anybody but assumed that was because the groom wasn’t local and her family were due any minute. I sat in one of the rooms at the registry office, waiting for the bride to arrive, still looking around. Thought I recognised her brother so started to relax a bit. In walked the groom and took his place. Fifteen minutes later in walked the bride… Who was a complete stranger!! Not only had I turned up and sat through a strangers wedding, I’d got the completely wrong weekend! I left the gift in sheer embarrassment and walked away at speed!

12. When I lived with my Mum I got caught bashing me old bishop one time. Mum was out at work so I took my chance to really get into it and got totally naked. Bit of a marathon session (way longer than my usual few minutes!) – noise on full volume (no headphones this time my friend, this was to be the wank of all wank’s). Anyway, I finished me business and felt a bit worn out. So I went out to the kitchen, cock-in-hand to get a drink. Only I didn’t get to the kitchen – My mum was sitting in the hallway trying to hide her embarrassment by making it seem like she was reading a book. She played it cool: “Hi ******”. So I (again, cock-in-hand-having-just-finished-myself-off) followed suit: “You alright Mum?” then proceeded to the kitchen, got a glass of water and walked back past her upstairs to my room in silence. Awkwardest moment of my life thus far.

13. I was a about 14, in year 9, in a Spanish class. One of my friends had told me not to sit on the table because it was broken I sat on it anyway thinking it wasn’t that bad! The whole class arrived to start the lesson so I moved to get down from the table but ended up going straight through it!!! I was wearing a skirt because it was hot that day and forgot to put shorts on underneath because I was in a rush, the entire class saw my underwear including my teacher! I went bright red and ran home.

14. I use to get extremely heavy periods, this particular time was really bad! I was with some mates at one of our male friends houses, I could feel I needed to check how it was going down there but felt too embarrassed to get up from his bed just incase I’d leaked! When I did eventually get up I decided not to look behind me and ran straight to the toilet. When I returned they had covered up my leakage, I noticed when I moved the cushion to sit down, I’d left my mark on his bed!! I was mortified! I had to go on the pill after that in the hopes it would lighten my heavy flow!

15. Ok so I was at my friends flat before a night out for pre drinks and by this point I’m pretty drunk. I was just coming off my period and thought I’d be safe and pop a tampon in as I was wearing a dress. It was uncomfortable so I nipped to the loo to change. Someone went in after me only to shout out to everyone that there was a tampon left in the toilet!! I thought I’d flushed it! Still haven’t lived it down almost a year later. Worst moment ever!

16. I was at Waterloo station with my 18 month old when I needed the toilet, whilst on the loo my little girl pressed the panel that opens the door. The door opened onto a really busy platform and there I was trying to get off the toilet, bare behind, with my daughter cracking up behind the door! Sixteen years later she still has that same damn twisted sense of humour!

17. I was in a French lesson, we had a sub teacher for some reason. Anyway she was unbelievably good looking & had a really smooth, sexy accent. I don’t usually pay much attention in this class but that day the teacher had my full attention, both eyes on her, and that deliciously perky butt. Anyway she calls me up to present the slideshow she has. I’m really not up for moving off my seat at this point because I’ve got a massive boner! She takes me by the arm to get me in front of the class, I’m trying to come up with excuses but she won’t take no for an answer! So what do I do? I pretended to faint to hide my lack of self control down there. She starts freaking out and calls the schools medical office. I spent the rest of the afternoon in the nurses room, they called my parents & I got to go home early. Trying to explain what had happened was utter torture!



  1. Lilinha Espindula February 18, 2016 / 5:28 pm

    Very interesting post, I must say I was laughing at their embarrassing moments. It is kind of reassuring to know that embarrassing moments happen to all of us!

    • cheskaaanels February 18, 2016 / 5:32 pm

      Haha yes I agree!! You don’t feel quite so alone anymore!

  2. Faye February 18, 2016 / 6:12 pm

    Great post! Embarrassing moments are the worst! Some really great ones up here. Made me think of all the embarrassing moments I’ve had in the past. Eeeek. Good to know it happens to us all, eh?

    • cheskaaanels February 18, 2016 / 6:14 pm

      Oh absolutely!! I’m so pleased it hasn’t just been me!

  3. Raymond February 19, 2016 / 7:21 pm

    Wow. Some of those are deathly embarrassing. Really felt bad for that poor bloke and his Mum lmao.

    • cheskaaanels February 19, 2016 / 7:34 pm

      Haha likewise!! Has to be one of the worst!

  4. Ana De Jesus February 20, 2016 / 9:40 am

    Haha I have so many embarrassing stories. A friend took a photo of me in university year which I did not realize you could see my underwear and I was pulling some dodgy pose. The bullies from secondary school somehow saw it and posted it all over social media telling everyone that I was sending boys naked pictures and then a load of people that were meant to be my friends freezed me out and said that I deserve to be given hate.

    • cheskaaanels February 20, 2016 / 9:53 am

      Oh my gosh! Some people can be ridiculously immature! At least you know who your real friends are now!

    • cheskaaanels February 20, 2016 / 1:48 pm

      Haha thank you! Was a pleasure to do!

  5. Lima (@Fashionicide) February 21, 2016 / 8:27 pm

    This was a fun read – although I’m sure you must have wanted the ground to swallow you up! Sometimes I do say things out loud that can make me appear ditsy but hey ho, better out than in *laughing crying emoji*



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