10 Women Revealed Their Most Cringeworthy Dates Ever & SOS, They Are So Painful

by Christy Piña

When you look back on your past dates, there's probably one that takes the cake as the most cringeworthy. (And if there isn't, I'm jealous.) Whether your date wouldn't stop talking about themselves, or they decided to wear crocs and basketball shorts to take you out, something about that date likely stood out to you and made it the worst. It happens, and it's nothing to be ashamed of, but it can be something to laugh about down the line once you've gotten over the awkwardness of it all. These 10 women revealed their most cringeworthy dates ever, and if misery really does love company, you're going to love these.

Cringeworthy dates suck, but they're not the end of the world. (Unless, you know, the apocalypse actually is here, but that's a story for another time.) The date may feel really awkward and uncomfortable when you're going through it, but once it's over, good news! It's over. Go home, eat a pint of your favorite ice cream, and marathon-watch Game of Thrones. In any event, you've probably got a hilarious story to pull out of your back pocket. And if you need a little emotional boost after your most recent cringeworthy date, you're not alone. Read on.

At least he was nice.
I matched with this guy on Hinge, and we had been texting for about three weeks before I met him. I was super into him and couldn't wait to meet him in person when he got back from traveling abroad. The day finally came and we decided to meet up at his apartment first before going to the movies. But a couple of hours before meeting him, I got extremely nauseous and felt excruciating pains in my abdomen. I knew I had to poop. So before the date, I let it all out at home. (Or so I thought.) Then I drove 30 minutes to see him. Even though we didn't hit it off like I expected, I could tell he was genuinely a nice guy. We hooked up almost immediately, but I was still battling the stomach pains.
As we cuddled on his couch watching a basketball game, I could feel the pain return. This time it was more extreme than the first time. I had to go again. But the only bathroom he had was downstairs, next to the couch where we were watching the game.
Eventually I was honest with him and told him my situation, he drove me to the nearest Whole Foods so I could empty my bowels. He stood outside the entire time and even bought me water bottles as we left the place. Then, we watched a movie in peace. Like I said before, he was a really great guy, but I never talked to him again.

Ella*, 23

I'm sure she never lied to a date again.
Sergey Filimonov/Stocksy
I went on a first date with a guy from Tinder. Not only was he significantly shorter than I expected (which, no shade to short people, I myself am 5 feet tall), but I also did not feel an ounce of romantic chemistry between us. I fled to the bathroom to text my friends for advice, and found out that a few of them were bar-hopping nearby. I decided I'd use them as an out. (I'm a horrible person.) When I went back to my date, I told him that I was ready to head home, and that my "cousin" was nearby, so I was going to Uber home with him. He insisted upon walking me to my "cousin," so he came face-to-face with the friends I was supposed to "go home" with. My "cousin" (played by my very clueless guy friend) said, "We're going to Shots!" (a nearby club) and I gave him a death stare and said "No! We're going home!" and he said, "Oh, yeah. We're going home." I said goodbye to my date, went "home" with my "cousin" and his friends, but instead of actually going home, we did in fact go to Shots, where I proceeded to awkwardly run into my date. I panicked, yelled "I need to leave right now!" to my friends, and ran out of the club.
Looking back, I don't know why I wasn't just honest with my date and told him I was going to meet up with some friends. I guess I didn't want to hurt his feelings, but I ended up doing just that the morning after when he still texted me, and I opted to softly tell him the truth.

— Veronica, 25

That first red flag was already enough to make me cringe.
Jacob Lund/Stocksy
I once went on a date with a guy I met online who showed up wearing shorts and sandals with white tube socks pulled all the way up. That was the first warning. At the tapas place we went to, he insisted on getting a pitcher of sangria, even though I said I only wanted one glass. No problem, he would drink it all himself! And he did, all the while complaining about his job and telling me that he was only staying there long enough to make a year so it wouldn't look bad on his resume. All attempts to change the topic went nowhere. It was... awkward. So awkward. After the date he texted me to say what a great time he had and asking when he could see me again. I'm kind of ashamed to say I ghosted him, but what would you have done?? Thankfully, I was experimenting with a nickname at the time and had introduced myself with it, so he didn't have the name I used regularly. Suffice it to say that I never used that nickname again and was a lot more careful with my online dating screening after that.

— Leah*, 29

Definitely the messiest date ever.
I went on a date with this guy I was secretly sort of dating/hooking up with who I worked with. It was already awkward because he was dressed super casually, and I was kind of like in a revealing top and tight jeans and booties (lol a past life for me). We went to this fast-casual Persian restaurant, where you get food on trays. I was telling him a story about these two girls from New York, and I was getting really into it and talking with my hands, which I do when I'm nervous. I went too far and just knocked my tray with my hand during a passionate sentence and flipped all of my food, and it went flying all over me and the floor and him, and I got on my knees to clean it up, and it was so awful. It was fine though. We went out again and I think maybe even hooked up after that, but he went on to break up me on Valentines Day so, not meant to be. Maybe that just sealed the deal that I was not chill enough for him.

— Iman, 24

So wrong on so many levels.
Danil Nevsky/Stocksy
Honestly, my most cringeworthy date was once a guy came over to Netflix and chill — which on my end was strictly Netflix seeing as we had never actually met in person, but whatever. So he gets to my place and literally like three seconds into talking to me, I notice he’s starring at my chest so I kinda gesture (with my eyes) to see what he’s looking at and he looks me dead in the eyes and asks if my boobs are fake. I say no and shake it off and we continue to talk, then like 20 minutes later he interrupts me mid-conversation to ask if he could touch them..... again, I say no. After an hour or so of hanging out, he then asks if I would be interested in him talking to my boobs.... TALKING — I told him to please leave.

— Ann*, 21

jamie grill atlas/Stocksy
I went on a Tinder date in Brooklyn with a guy who seemed really cool, I thought we had a lot in common. We went to a bar, and he didn’t want to eat, which was fine by me, so I paid for my meal. We went to another bar to grab a cocktail, and he suggested we split the bill — OK, whatever. His drink was $12 and he gave me his card and a $5 bill to pay for his one drink… I suggested we just split the cards and give the $5 as tip. He was reluctant, but then gave in and his card was declined! For $12! When five minutes earlier he had been talking about how he dropped $1000 for new Yeezys, so of course, I was like, WTF? I ended up paying for him, and then when I got home, he texts me to ask if I want to hook up! And then goes, "Omg that wasn't for you!" He said he was copying and pasting a text from a girl who was texting him, to send to his friend! Needless to say, I never spoke to the dude again.

— AC, 25

Um, thank u, next, for real.
Kayla Snell/Stocksy
My most cringeworthy date was sophomore year of college. I thought he was a catch! He was tall, attractive and very intelligent. It took some coaxing to even get him to finally agree to go out for dinner together after we had been talking for a while. We went to a make your own pizza place and got to the register and he didn’t make any move to even offer to pay. I just chalked it up to the fact that he wasn’t American [and didn't totally understand western dating customs]. Fast-forward to eating the pizza and the guy proceeds to talk about nothing but himself the whole time, all his accomplishments and how smart he was — I could hardly even get a word in! Also, he hardly ate any of his food, and I ended up eating way more than him even though I eat like a bird (awk). After that date, he then proceeded to drop off the face of the earth only to hit me up over a year later professing that he was still in love with me and had just been very nervous on our date because he liked me so much. To this day he will still send me snapchats occasionally of things that remind him of me, even though I’m about to get married.

— Esperanza*, 23

One h*ll of a 21st birthday.
Studio Firma/Stocksy
It was my 21st birthday and this guy from Tinder asked if he could take me to see the new Star Wars movie. We get there, and he complained that the Military discount wasn’t big enough, so not off to a great start. Then, he asked if I wanted snacks, so I go order some candy and he’s just standing there and goes, "Oh I wasn’t gonna get anything." So, I pay for myself awkwardly. Then, he takes me to Wynwood [a nearby neighborhood] so I can be at a bar when I turn 21 and get my first drink! He didn’t want to pay for parking or cover cause he "wasn’t trying to spend money," so we just drove back home. On the way he called me a b*tch for not wanting to give him a blowjob. Happy birthday to me.

— Josie, 22

Great chemistry through text, not so much IRL.
Luis Velasco/Stocksy
It was a Tinder date. This is someone I was talking to for like two weeks already. I thought he was pretty cool, he was a really nice guy, and when I met him, we hated each other off of the very spot because he was far to the left, and I was far to the right. And we just completely disagreed on everything. Even when we agreed to stop talking about politics, just anything was an argument and anything was a very controversial conversation, based on values and based on beliefs, and everything. Literally, at the end of the date, I didn't even fight to make it seem like I was going to split the bill with him.

— Caroline, 23

I feel my skin crawling.
Alexander Grabchilev/Stocksy
In college, I met a guy on a dating app and we got burgers near campus. The conversation was so awkward. I tried hard to keep it up, but he kept giving me one-word answers and not ask me anything else. When he asked if we could get gelato after and sit in a nearby park, I was surprised to hear he wanted to keep hanging out, but agreed. We each got cups of gelato and sat on a park bench. He asked if he could try my flavor, took a spoonful, and put the spoon back in the cup. He said, 'Now that my germs have been in your food, I guess they can be in your mouth, too,' and pinned me to the park bench to kiss me with tons of tongue. Our chemistry was so terrible and I was so taken aback that I jerked away and lied that I just never felt comfortable kissing on the first date.

— Hannah, 26

Not every date is going to be perfect, and if you run into one that sounds anything like the ones above, don't let it get you down! Say "thank you, next," and keep on moving.