9 Funny And Embarrassing Lingerie Mishaps Because Underwear Problems Are Real, And So Not Sexy

June 16, 2024

Whilst researching horribly embarrassing stories in preparation for Valentine's Day, I discovered that there are two particular situations that seem to bring about the worst lingerie disasters: The fitting-room and the wedding. And I can totally understand why. In the fitting room, one is in a vulnerable position — half naked, trying on underwear that often doesn't fit well or look good. We are at the mercy of a total stranger who measures and stares at our boobs, which is a move we certainly would not accept in everyday life. As for the wedding, most of us feel the need to bring out the agonizing shapewear, and any possibly-visible bra straps need to be fancy and pretty. So chances are, we're uncomfortable from the get-go and wearing underwear we wouldn't wish upon our worst enemies. And let's not forget that weddings also involve two of the most effective ingredients for creating embarrassing disaster situations: Alcohol and dancing. Need I say more?

Before you set up a support fund for me and my disastrously embarrassing life, don't worry. Not all of the below stories are mine! I called on my legion of embarrassing/embarrassed girlfriends, bribed them with tea and biscuits and asked them to share their stories with me for this article. So a BIG THANKS to my girls on this one! Some of the stories, however, are mine — but now you'll never know which ones (insert evil laugh here)! No seriously though, my dad reads all my articles. I need to have the benefit of the doubt.

1. CHANGING ROOM MIX-UP

In the run up to Valentine's Day last year, I was in a very busy fitting room trying on some racy lingerie. I went all out: A see-through bra, black lace, red ribbons, matching suspender belt, stockings; it was enough to give the average guy a cardiac arrest. I wanted to get my boyfriend's opinion (mostly about the price tag) so I asked the lady to go get him. He was waiting outside, along with 10 other partners losing their patience. "He's the one with the baby," I said. Seconds later the lady returned, whisking the curtain open to reveal my sexy outfit to a very scared looking random baby-wearing stranger! I'm not sure which of us was more embarrassed!

2. I THINK YOU DROPPED SOMETHING

My boyfriend and I moved in together after a very short whirlwind romance and I had not yet met his family. The day came when my new brother and sister-in-law invited us over for dinner, and I decided to wear my new red stockings that my love had bought me (oh new love, remember that feeling?). Pretty quickly into the dinner I began to realise that the stockings were not the best choice ever. I had never worn stockings before and it seems that my legs aren't designed to keep them up. Every time I was sure no one was looking, I pulled the elastic back up as high as I could, and if that wasn't possible I scurried off to the bathroom to rearrange myself there.

Eventually, the evening came to an end and they walked us downstairs to the door. Halfway down the stairs, one of my stockings gave up any attempt to hang on and floated happily to my ankle. My brother-in-law, not realizing what had happened, thought I had dropped something and tried to pick it up for me. Realizing that he actually had my escaped sexy stocking in his hand, he dropped it like it had burned him and took a hasty step backwards, tripping on the bottom step of the stairs. So much for making a good first impression!

3. IT'S A CONFUSING WORLD OUT THERE

Getting ready for an important meeting at work, I decided to wear a new bra I had bought, which had visible straps as decoration. Maybe a bit racy but I figured they could handle it and it made me feel powerful and wonderful. During the lunch break, I was chatting to one of the important professors and he complimented me on my beautiful necklace. Sounds nice, right? But I wasn't wearing a necklace! Acting shocked, I replied, "Professor, that is my bra!" The poor guy looked as if he wished that the ground would swallow him up, muttered something into his coffee and ran away. So for once, I was not the embarrassed one in the situation!

4. WAVE 'EM AROUND LIKE YOU JUST DON'T CARE

It was a long time ago, but some traumas just stay with you forever. I was 16, sitting in a particularly dull class at school when my bra clasp decided to undo itself. There was an hour to go until the break, and the hooks were bugging me, so I decided to quietly take it off. To fill you in, I only wear bras for the idea of it. I don't actually need any support in the bust area; gravity has no impact on these puppies.

So, I start digging under my layers of clothes, sticking my arm in the neck of my sweater to get the straps off my shoulders. Then with a swift and skilled move, my right hand up the sleeve of my left arm to pull the strap down and free it from my arm. A quick look around to check no one has noticed — seems like I'm in the clear, of course I was sitting comfortably at the back of the class. The second arm, whoosh, my hand up my sleeve and I grab the strap: I can almost taste the freedom. I pull on the strap, ready to deposit the offensive bra in my school bag, but it seems to be stuck. The clasp has caught on one of my layers. Suddenly panicked, I pull a lot harder on the strap and this time it came loose. Unfortunately, the energy I exerted to dislodge it was excessive in the extreme and I ended up dramatically waving the bra above my head for everyone to see. My teacher's jaw dropped and his whole head turned a special shade of crimson, which caused the whole class to turn around just in time to catch me stuffing the bra in my bag. It still makes me laugh if I think back on it, and you know what? I still take my bra off like that. If I'm relaxing in the sofa and it starts to bother me, whish, whoosh, tadaa, and I'm free! But without an audience!

5. WOULD YOU LIKE TO TRY A PARACHUTE MADAM?

I have a confession to make. Please don't hate me for it, but I don't know what bra size I take. We all know that no two brands have the same sizing and that boobs can grow or shrink depending on a whole load of factors, so personally I don't feel so bad about not knowing my size. However, ladies in fitting rooms and women in general seem to react in shock and dispair when I admit this: How can you know know that? What is wrong with you?

So this one day I was in the mood to buy myself a pretty, delicate, fancy bra, I wanted to treat myself and get something really nice, you know, with lace and ribbons and a special color. In an effort to not seem so crazy and out of touch with my body, I picked up a few bras that I thought would fit me and headed off to the fitting room. As per usual, not one of them fit perfectly; they were either pinching or gaping, or you know, is there a term for a boob muffin-top? So I plucked up all my courage and asked the boob lady to measure me and bring some similar bras in my size. She hummed and hawed and eventually said "Oh they don't make any of those bras in your size, come out and I will show what we do have." Annoyed to have to get dressed again I followed her to the section with my size, when I saw the options my heart sank into my shoes and all desire I had to buy a bra that day vanished into thin air. Apparently, the only bras suitable for my mega boobs were white or black, cotton or support fabric, with straps as wide as my shoulders and busts like parachutes. I thanked the lady and politely pretended to inspect the options until she was out of sight and then I high-tailed it out of there.

6. ATTACK OF THE KILLER UNDERWEAR

Delighted with myself for having found the perfect red dress for an upcoming wedding, I tried it on at home only to realize that the back and underarms of the dress were really low, meaning that you could see my bra from every angle. I called the shop where I bought it to ask what lingerie people usually wore with this style of dress. "The designer meant for you to wear a visible black bra," she said smugly. "Well, the designer has never been to a traditional family wedding with my in-laws," I thought, hanging up the phone.

So off I went to a specialist underwear shop and came home with a bodysuit that buttoned at the crotch and was invisible everywhere I needed it to be. It also had the added bonus of keeping my belly under control and making me feel like Gwenyth Paltrow. I know they say pride comes before a fall, and I was seriously proud of my purchases. I guess I should have known it couldn't last.

The day of the wedding I got dressed, and after one last twirl in the mirror we walked the short distance from the hotel to the church. We were a little bit late (as always) so everyone was standing awaiting the arrival of the bride, we shuffled to our seats and stood until the bride had walked up the aisle. Glad to finally be able to sit down (yes my shoes were already hurting me). I took my place, smiling politely at the people already looking at us because we were late. Then, with a squeal of pain, I jumped back up out of my seat, attracting the attention of anyone who wasn't already staring. Red-faced, I slowly eased myself back onto the chair and looked around as if to suggest someone else had made the noise. Turns out, my miracle bodysuit was not as long as my torso and upon assuming a seated position, the unforgiving lycra decided to cut right up into my private parts! Normally I really enjoy weddings, but I couldn't wait for that one to end. It was really difficult to think romantic thoughts with a stabbing pain between my legs. After the ceremony, I rushed to the bathroom and closed the bodysuit over my tights, which made it almost bearable, and after a few glasses of wine I no longer cared about the VPL situation.

7. THE MYSERY OF THE STOLEN UNDERWEAR

When I was a teenager, I had to go into hospital for an operation. It was my first time ever in hospital (besides being born, obvs) so I wasn't down with hospital gown etiquette. When the time came to put on the offending hospital gown, totally open down the back, I wasn't sure if I should leave my underwear on or not. So not wanting to be walking around with my bits hanging out, I decided to leave them on. I figured they would ask me to take then off when the time was right. Right?

Four hours later, I woke up with no recollection of anything following the underwear decision, but one thing I realized very quickly was that my bra and underpants were missing. As I was only 16, I was far too shy and embarrassed to demand their return. Even though the bra was new, denim effect and from a trendy brand that I had saved up for, I didn't want to admit that I had made the wrong decision by not wanting to take it off.

So my parents drove me home, secretly braless and pantless. My mother, in an effort to impress the medical staff, was dressed "for town" and was doused in Chanel No. 5. To this day, the smell of Chanel No. 5 gives me a sick feeling in my stomach and I feel a wave of shame just as powerful as on the day I was drugged and had my underwear stolen.

8. YOU GOTTA ROLL WITH IT

On a particularly wild night out, I was strutting my stuff on the dance floor, feeling like a diva, head to toe in shapewear, loving the attention I was getting from the cute guys shaking their booties around me. I was channeling Beyoncé big style when I felt a strange tight feeling around my ribs, but not wanting to interrupt my dance routine, I ignored it, quietly cursing my fabulous shapewear. Then I noticed that the facial expressions of the flirty dancers had changed and I knew something was really, really wrong. Turns out, my super-tight underslip had rolled itself up to my waist taking my dress with it. In case you have never experienced the boa constrictor-like agony of rolled-up shapewear, that shit is not easy to unroll! So there I stood, in the middle of the dance floor, exposed from the waist down with no other option than to walk across the whole club in a semi-clothed state to get to the bathroom. Needless to say, I went home pretty soon after that!

9. THE GREAT WEDDING ESCAPE

My boyfriend and I were at a friends wedding and were both dressed up to the nines and looking fab. We had been giving each other the eye all evening and finally managed to escape the wedding conversations to slip away to a more, em, private area of the hotel. We ran down a stairwell, pausing for a passionate smooch on the way, skipped through a deserted function hall, and found ourselves in a quiet hallway somewhere between the staff rooms and the kitchen. I'll spare you the details but needless to say we were pretty red-faced when a fancy posh waiter appeared from nowhere and asked us to return to the wedding party. Grasping desperately at discarded items of clothing and getting out of there as quickly as possible, we returned a little disheveled to the party. "Give me my bra," I whispered to my boyfriend, who's only response was a rather shocked shaking of his head. We rushed back to the function hall but the waiter had locked the door. Too embarrassed to ask him to open it, I resigned myself to a braless evening and did my best attempt at channeling braless Beyoncé. Chin up, shoulders back, here we go!

Images: Fotolia; Giphy; Instagram/Katylegs; Author; Flickr/Lies Thru a Lens;

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