People Are Sharing The Worst Ways They Ever Ruined A Date (15 Stories)

If dating were easy, there probably wouldn’t be thousands of apps dedicated to making you hate it less.

It’s inevitable that the dating phase of any relationship is super susceptible to f**k-ups and awkwardness. After all, you’re getting to know each other, and that doesn’t always come naturally (especially if you’re forced to sit down at dinner and pretend you’re NOT sizing each other up).

However, it should comfort you to know that, regardless of how much you might screw up on a date, you will still probably never screw up more than these Redditors on r/TIFU:

15. This is why Austin Powers references are CANCELED.

This happened about an hour ago and I’m still cringing.

So I’m sitting opposite an attractive and funny woman I met on tinder. The conversation is flowing, we’ve just discussed movies and we’re having a laugh. It comes up in conversation that my father is Dutch. She asks me if he’s a crazy Dutch guy and if I’ve inherited any crazy Dutch traits.

“Oh yeah”, I say without hesitation. “I totally eat my own skin flakes.”

Blank stare.

“I carry them around with me.”

Nervous laughter. Looks over my shoulder.

That’s when the penny drops. She didn’t get the joke because she hasn’t seen Austin Powers. Cue very awkward explanation and very weird call backs throughout the night to eating skin flakes.

The date ended with her saying I’m “interesting”. Pretty sure I’ll end up alone with permanent cringe lines on my face.

TL;DR made a spectacularly weird movie reference during a first date that ended with us both being grossed out.

Edit: quick update as I’m about to head out. Turns out I may have written about the wrong fuck up here. I knew before the date the other night that she likes to draw little pictures, so I took a small notebook and pen to the date and joked she could use it if she got bored. She took that in the humerous spirit with which it was intended, but insisted I take it home with me at the end of the night. She texted me the next morning, and now I’m about to meet her for our second date. I’m one lucky redditor.

The real fuck up here was focusing so much on a silly mistake and not focusing on her. To those of you who gave such kind words of encouragement; thank you. To those who pointed out my social ineptitude – well, duh. I’m an awkward dude with anxiety who is somehow about to have a second date with a lovely woman who has looked past all of that. Bloody hell.

And the notebook? It fell out of my jacket pocket this morning when I finally put it away. She had drawn me a picture without me knowing, probably whilst I left her for a moment to use the bathroom. She drew a picture of a skin flake and wrote “skin flakes are cool.”


14. To be fair, choosing between chocolate and sex is kind of a Sophie’s Choice.

So I was on a date with a girl to the cinema. The date went well, but it was only a second date, and I still didn’t know if she liked me or not. So she went to the bathroom, and I decided to go to the shop next to it while waiting. Now we had gone to see the hobbit and I was starving as i hadn’t eaten since dinner before, and I didn’t feel I needed a snack during it, and I didn’t want to ask her for some in case she thought it was weird. So when I went to the shop I saw condoms, and I started to ask myself if I may need some myself. Now I’m a 19 year old virgin, so I’m very oblivious to any signs of interest from girls, and I never had a need to already have condoms. Now I only had enough money for the condoms by themselves, and then I wouldn’t have been able to afford the chocolate. So I bought the chocolate. BIG MISTAKE. I drive her back to her college apartment, and walked her to the door. She then invites me inside for some tea. Now being inexperienced and kind of clueless I think she genuinely means a cup of tea. So we are there sitting on the couch drinking tea when she leans in and starts kissing me. Things escalate and she’s dragging me to her room and we start getting undressed. Then she ask the dreaded question, “Do you have a condom?” So now I’m sitting here, still a virgin, with a mars bar wrapper in my hand. TLDR: Bought a bar of chocolate instead of condoms while on a date, and now I’m still a virgin because of it.

Edit: wow thanks for the response guys it is really helpful. I decided to take the advice of a few of you and rang her. Things seem all good, and she wants to go out again. Pretty clueless as to what I’ll do, but I’m definitely not forgetting the condoms.


13. Don’t go on a date with Norman Bates, ladies.

I met a guy online, and we have been talking/snapping/texting for about two weeks. Our first date was supposed to be Friday, but he really wanted to meet me, so I agreed to meet him at his house once I got off work (at midnight.) I pull up to his house, and his mother (I wasn’t aware that he lived with her) came out and told me that I shouldn’t be showing up at her house to fornicate with her son in the middle of the night. As I was turning to leave, he comes out and apologizes for her behavior, and tells me that she’s just looking out for him. He then says that they had had quite a few drinks. As he was explaining that she acts insane when she’s drunk, not to mind her, he suddenly throws up all over me. I had to drive home covered in puke.

EDIT: Wow, front page. I didn’t realize my massive fuck up was that massive. Also, I have learned my lesson. No, I did not go to his house with even the intention of going inside. It was supposed to be talking for a bit, and then I go home. Thanks for all the concern, but I do understand how stupid of a move I made. The vomit taught me a lesson.

EDIT: Gold?! Thanks! Good to know my awful experience has made a lot of you laugh. I am laughing with you. 🙂


12. Wrestling is sexy — until it isn’t.

So yesterday was Valentine’s day and I’ve been seeing a girl who used to wrestle when she was younger. I was a wrestler for 10 years and we both knew this. So we get drunk last night and start messing around on the couch. We’re just using moves on each other and I’m winning.

We do this for a while and it’s all fun and games until she says “I bet I can beat you from the standing position.” We are both pretty trashed at this point so we stand up in her living room and start facing off. We tie up with each other and instinct kicks in so I sprawl and slam her head into the hardwood floor. I spin around behind her and then I realize she isn’t moving.

At this point I realize that I fucked up badly. She comes to and she has a huge black and blue knot over her eye brow. I’m feeling like a gigantic piece of shit and after a couple of seconds she laughs and says it’s okay.

So the TL;DR here is that I got trashed on wine with a girl. We wrestled. I knocked her TF out on a hardwood floor. Now she has a lump like a pachycephalosaurus on her head.

Update: Holy shit this blew up. For the folks concerned about concussion: she’s a nursing student so when she had clinicals the next day she got herself checked out. She’s good to go.


11. I mean, at least they’ll have a hilarious story to tell their grandkids…?

EDIT: … and Scene. SHE FOUND IT. 5:15pm EST. 5 hours. Good work guys!

I have been “dating” again, and like many 20-somethings in Brooklyn, I have been doing with the aid of the internet. After browsing the dating pool on the popular dating site “OKCupid” I found myself texting this girl a couple times. I suggest we meet in prospect park and walk around.

For those of you who have never been, Prospect Park is a bit bigger than your standard “park.” Designed Fredrick Law Olmstead in 1850something, this thing is almost 600 acres with tons of small paths and arches and small corners. When she suggested we bring a couple canned beers along for the walk, I was into it. I figure, keep them in bags, spend some time on the lass traveled bits and have a nice date walking and talking and sipping.

Around 2 hours into our date, we find a nice little bench by the water to hang out. After about 20 minutes of chilling a GIANT police cruiser pulls up. Anyone who is relatively irresponsible in New York knows what happens next: they take your ID, run it to look for warrants, and after they determine you are not wanted for anything more serious, they write you a $25 ticket and leave you alone.

We sit on the bench for what seems like a while, patiently waiting for them to do their thing, making short jokes about our records and how this is going to make a great story. I noticed there was an issue when I saw the first office get out of the car with only one license/ticket. The other guy got out and started unloading the stuff from his back seat to the trunk.

I vividly remember getting an open container offense a couple years ago (different park), but I only vaguely remember paying my $25. Turns out I didnt. 2 hours into a first date, I am in handcuffs, asking her to look after the other 2 beers I brought. There is a small crowd, and right before they cart me off I blurt our “soo,, I guess I will call you?” WINK.

EDIT: My roommate (sitting across from me) just told me that her friend sent her this link not knowing it was me. I feel like its going to get back to the OKC date. Reddit always finds a way …


10. Honestly, this guy sounds like he’s a champ.

TIFU by inviting this guy(25M) I’m trying to woo over to my (25F) house for the evening. We’ve been on a few dates, but I was pretty sure this was going to be the deciding date on where things were going. Anyway, we’re chilling out then decide to smoke some weed. Which usually is fine I can handle it. So smoke two joints, make tea, and go upstairs.

All is going smoothly until suddenly I feel THE FEAR and PARANOIA coming on. We all know it. Lying there trying to act cool and chill…. Until eventually I just have to tell him to please stop talking and that I am going to die…. Dramatic I know now. I tell him to go downstairs to get housemate/BFF to come save me. At this point I am frozen on my back in the bed with the worst paranoia of my life. I’m (for some reason) convinced that Guy Crush is a weirdo and WTF is he doing in my room he’s going to kill me… But still trying to play it cool…. Not for long.

Housemate comes in, and obviously finds it hilarious. Guy crush remains in room being all comforting and nice… But deep down I know he’s a serial killer… I try to communicate this with my eyes to my housemate…. Obviously not very subtly either as she is still finding it hilarious. She gets me 7UP and Haribo to try help me comedown… While still taking the piss asking would I also like dreadlocks with that.. Or maybe we can listen to some reggae. She reassures me nothing out of the ordinary is happening…. But not in my head.

The Fear begins to get so bad that I start to jump at every sudden movement that Guy Crush/Serial Killer is making. And then… Of course to make matters worse… In a scene reminiscent of when Chandler takes a bath in Friends, or when Ben Stiller gets himself stuck in his zipper in the film Something About Mary… The rest of my housemates are at the door sticking there heads in wondering Hey why is everyone in here, what’s going on… Then see me frozen on my back in the bed with eyes as big as saucers and they finally back away…and I hear the giggles starting from downstairs. This doesn’t help my paranoia as I convince myself the only way out of this situation is to burn the house down.

Still very conscious of Guy Crush/Serial Killer beside me…. He reaches out a hand to comfort me… This is the last straw.. I jump about two foot into the air and tell him HE HAS TO LEAVE. He leaves… The room.

Once we’re alone, I tell housemate she HAS to get him out of house before he kills us all. She reassures me Not to worry… About a thing… Cuz, every little thing… Is gunna be alright. -_-

We sit for what’s probably an hour of me jumping and tuning into every little sound the house is making… Waiting for it to fall down or a chainsaw to roar from downstairs. Eventually it turned out Guy Crush just left without saying anything… After his DAD had to collect him (I was supposed to drop him home). He left a note saying not to worry about it and it happens everyone… A note I immediately interpreted as a blatant death threat in my Fear riddled state.

After he has left, I eventually ride it out and I go to sleep. Have to get up for work the next morning and literally have just pretended like nothing has happened. Which I will continue to do for the foreseeable future. Could the date have gone any worse? No.


9. Remember: karma is real, and karma will f**k up your casual dating life.

The obligatory this actually happened last Friday. I met up with a guy from Tinder (we’ll call him Tim) for a date. It was actually going pretty well, we had stuff in common and didn’t seem as awkward as most dates. Drinks start flowing, I’m having a good time, and the night moves on.

After we got to the 3rd bar he looks at his phone and says “hey, my best friend (we’ll call him Steve) is in the area, would you mind if he stopped by for a drink?” I was having a good time and didn’t care so told him to invite him over.

We proceed to another bar where Steve is going to meet us. I then kick Tims ass at Street Fighter and am still having fun, oblivious to what’s about to happen.

In walks Steve and the world stops. I immediately recognize the guy. How you ask? Because a week prior I was talking with Steve on Tinder, we made tentative plans to meet. When the day came and he contacted me to confirm plans, I just wasn’t feeling it. So I was a shitty asshole of a human and blew him off by not responding and just deleted him. Trust me, I know it was an awful thing to do and Karma chewed my ass right back…

So Steve walks up to us and it’s awkward as fuck. Tim introduces us and instead of saying the usual “hi” he starts laughing and shaking his head. He says he needs a drink and walks off. I immediately tell Tim what happened and take credit for being a shit stain for doing that to Steve. Tim just awkwardly laughed and didn’t say much.

Steve returns, it continues to be weird as fuck (I deserve it). I try to cut the tension and just straight up apologized to Steve for being a douche bag. Tension got worse. Nobody was saying anything. I had to get out of that situation for a bit so I announce that I’m gonna use the ladies room. It’s notoriously nasty in this joint so I leave my jacket behind.

When I came back both Tim and Steve were gone, and they took my jacket with them. Thankfully bartender saw the whole thing so didn’t charge me for their tab, I tipped him well to start being a decent human.

TLDR: I blew off a tinder date, then a week later ran into him whilst on a date with his best friend. Got ditched and my jacket was stolen.

Edited for further clarification: 1) To clarify for several people and the haters. I didn’t stand Steve up or leave him waiting anywhere, we had nothing solidly planned and I just didn’t respond when he messaged to make plans. I feel like I took the higher road and not only told Tim about it, but I straight up apologized to Steve as well. 2) I still highly doubt the whole thing was planned. Why would Tim spend several hours with me having what seemed to be a decent time, just to mess with me and ditch me? He honestly seemed like a good guy and up until the ditching and jacket incident.

Update 1: I called Tim and he HASN’T blocked my number. I left a friendly enough voicemail so will update if he calls back.

Update 2: Thanks for the gold!!! 🙂 Was honestly not expecting this to blow up the way it has. All of these comments add to the hilarity of this whole story, even the shitty ones. You guys crack me up! Still no word from Tim though.

Update 3: This story just keeps getting better and better. Tim called me back! Super busy at work right now so I’ll update details when I have time later today.

Update 4: Sorry all, work was just insane today.. So Tim called me back! Here’s what he told me: when I went to the bathroom Steve flipped out, grabbed my jacket and left out the backdoor. Tim goes to follow Steve to calm him down and to get my jacket back because (obviously) it’s just stupid he took it. Steve starts running, so does Tim, they get into a bit of a live Street Fighter match and Tim’s phone gets busted during this process. By the time he returned to the bar I was gone and he couldn’t get ahold of me until today when he got his phone back. He also paid the bar tab. Apparently the bartender was dying when he heard this whole story and was prepared to tell me what happened to Tim, but I never went back to that bar. He has the famous jacket and we have a second date planned tomorrow to make up for the craziness of his friend and to return my jacket. He says Steve is cool with everything now, was just way too drunk, and he way over reacts to everything anyways. He definitely wants to hang out again, but I’ve learned my lesson and will be more communicative about actually making plans with people in the future. TLDR: Steve is in fact a douchebag, Tim is a hero, I got my jacket back. Bro’s before hoe’s my ass.


8. Maybe try dating someone with a sense of humor next time?

So because of circumstances beyond my control this didn’t happen today.

Cue my first date with a girl I met on Tinder, we meet up at a restaurant and get to talking. This are going great, she thinks I’m funnier in person (when does that ever happen?!), she actually invites me to the mall to hangout more with some of her friends when dinner is over.

So after the food arrives the conversation turns a little more towards how we met (pay close attention and you will spot my mistake). She states she’s glad I’m normal and not some sort of serial killer.

Now I could have just laughed… I could have but I was funny remember? I replied with “Oh thanks for thinking I’m normal! But I actually am a serial killer, bodies for days buried out at the farm.”

She laughed, I laughed, I thought I did great at making it sound sarcastic.

She excuses herself to the bathroom to do whatever girls do in bathrooms on dates. It was taking a questionably long time for her to return and I was slightly worried she bailed and stuck me with the bill, my luck right? Wrong.

So unbelievably wrong, my luck was worse as police officers suddenly appear out of nowhere and tell me to keep both of my hands visible on the table.

At this point I’m confused, this must be a joke. I see my date coming with a staff member and get ready for Ashton Kutcher to appear, no such luck.

The police ask if it’s me and she says ya, the cops get me to stand up and handcuff me and walk me out, not a single person seems to want to answer any of my questions.

I’m in the car and the police are outside talking to my date for a few minutes when they get into the car with me and ask me if I told my date I was a serial killer, areyoufuckingkiddingme…

I tell them yes but I was joking.

LPT: Don’t admit to police you told someone you were a serial killer.

So that derailed my plans, I spent the next 5-6 hours explaining myself over and over and over that I was kidding.

I guess eventually they either believed me or got tired of hearing me speak much to my lawyers disapproval (to me speaking) and let me go and reminded me that my jokes suck.

I’m not sure how date number two will go but I’m excited to find out, also a bright side is that I have no idea who paid for my food.

TL:DR: I made a joke I was a serial killer, date doesn’t get sarcasm, I spend hours in the police station.


7. Don’t try out any crazy pubic landscaping right before a date.

Just to give some backstory before my big fuck up.. I had organized my first date with this girl I had been talking to for quite some time. The plan was to cook and invite her for dinner and afterwards take her to see one of our mutual, favorite bands. But before the date, after checking my genital area, I decided it’d be smart to make sure they’d be presentable in case anything were to happen afterwards. So I sat over the toilet, grabbed some trimmers, and went off on my bush like I was Edward Scissorhands or some shit. At the end of the cut there was a mound of pubes sitting neatly in the toilet. I pulled on the flusher, closed the toilet lid, and jumped in the shower to clean myself off and get ready for her to come over. Half an hour later she enters, we exchange greetings, and the dates off. Date goes perfectly and we click immediately. Midway through the dinner she asks if she could use the bathroom and I kindly point it out to her. “Down the hall, on the left.” However, once she stepped out of the bathroom, something changed. It suddenly became harder to keep a conversation, she seemed increasingly uncomfortable, and a sense of awkwardness hung over the rest of the meal. Confused at what happened, I excuse myself from the table and head to use the bathroom. When I lift the toilet seat, lo and behold, sitting right dab in the middle of the toilet bowl, I’m greeted by that neat pile of pubes I had cut earlier. Of all the nights, my toilet decided it’d be best to break on the night of my date with a girl I had been pursuing for weeks. I head back to the table, get on with the rest of the date, and never bring up a word of that clump. Fml.

tldr; Trimmed my pubes over the toilet, toilet broke, date was met with a pleasant surprise.

EDIT: Can’t believe this blew up overnight and I’m glad you guys are enjoying this TIFU. This is my first reddit post so I’ve been leaving replies to the comments to give an update on the rest of the night but it seems like it just gets lost so I’ll leave it here. Rest of the night went a lot better than I had expected. We had a couple drinks over the course of the night which leveled out the mood. On her way out we kissed and she was off. We’re still talking today, so if any of you guys are having trouble keeping a girl interested, the secret might be to just leave some pubes in the toilet.

EDIT: Wow.. to the kind stranger who sent a gold my way, thank you! May toilet pubes always be absent (or present, depending on your preference) in your life.


6. Asking for a name is usually a good rule of thumb.

So I match with this cute girl from tinder. The conversation is flowing and I suggest we go out for drinks this past Friday. She agrees and we set the time and place.

When I arrive at the bar 10 minutes early i try to see if she already arrived and I see her standing by the bar. She made eye contact with me and I greeted her. We started talking for quite sometime and I was getting weird vibes from her so I suggested we go grab something to eat. We get out and as I see her more clearly under the street light I exclaim “you don’t look anything like your tinder profile pictures”. That’s when it hits me… This is not the girl I had a date with and just straight up hit on some random girl. I try to ask “you are not Melanie (name altered)” and she seems pissed of that I don’t remember her name but I’m more confused than ever.

I look at my phone and see 5 angry text messages and 3 missed calls.

My new date didn’t find it amusing and lost interest and my original date wants nothing to do with me.

Spend the rest of the night eating take out pizza and watching Netflix

TL;DR: accidentally hit on a girl in a bar that looked like my tinder date. Fucked up both dates.