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“Couldn’t Really Believe It”: 83 Men Recall Their Absolutely Worst First Dates With Women
First dates can be as nerve-wracking as job interviews. You’re trying your best to create a strong first impression on a potential romantic partner. But in doing so, many may end up doing the exact opposite.
This holds true for both men and women, but for today, our focus is on the ladies. You’re about to read cringe-inducing stories after someone on Reddit asked, “What’s the worst thing a woman has done on the first date?”
You may find yourself chuckling at some of the posts you read, but overall, these personal accounts are sad and unfortunate. If you have similar experiences or stories you want to share, feel free to do so in the comments.
This post may include affiliate links.
#1
My first date after throwing my ex out. It was awkward, but I was sure it was because it was my first date with someone new in 20 years. After I buy her wine, we have a nice meal and talk. Walk out of the wine bar and are talking. I tell her, "I had a nice time, I will call you." To which she responded, "earlier today I got back together with my ex boyfriend and we are dating again. I just wanted to tell you upfront"
To which my response was, "Telling me upfront is before I buy you wine and dinner".
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#2
I showed up to grab a drink and she was already blacked out. Chatted for 30 minutes and left. The next day she messaged me asking why I never showed.
#3
It was a blind date before the Internet was a thing. She drove up in a Lexus her parents bought her, I showed up in my 10yo truck I paid for with jobs during high school. She proceeded to go off about me being a poors for 10 minutes until I lost my cool and ripped into her and made her cry.
#4
The most confusing one I’ve ever had was when I met this girl at this place. We sit down, some nonchalant BSing, normal stuff. She asked me when my birthday was, I told her, she goes “Oh! You’re a LEO?!?! What the [hell]?!”, and the she got up and stormed out.
I was like “Hmm. I may have just dodged a super ultimate bullet there.”
#5
Her husband, which I did not know existed, showed up to the movies asking who the hell I was.
#6
Asked her on dinner date, she invites her whole entire family & expects me to pay the whole entire bill by myself. I stole some breadsticks & left.
#7
I had a woman at a first date start complaining about how awful it was to have to live around [black people]. AT a mixed race coffee shop. Loudly.
#8
Slapped me
We were having a fine dinner, enjoying each other’s company more or less, until she told me she was glad she didn’t cancel on me. This grabbed my attention a bit, so I asked what she meant. She wanted to cancel bc my mom and I interact semi regularly on social media, and that made me a mommas boy. I pushed her a bit on this and she started saying how weird it was to be friends publicly with your mom. She insisted on the importance of a distant relationship
I don’t consider myself a mommas boy, but we have a great relationship, and I’m very grateful for this.
I didn’t say much the rest of dinner, and when we finished, I drove her home. She was upset the date was ending early, and after talking for a few seconds, asked if it was because I was “insecure about being a [boy] who needs his mom”. I told her to get out and not talk about my family or me like that. She slapped me, told me to [get lost], slammed the car door and blocked me
I still laugh about it every time it comes up, couldn’t really believe it.
Daisydaisy 33 minutes ago
I'd rather go out with a man who's friends with his mum than one who's not!
#10
Showed up knowing he had popped positive for Covid the day before. Casually mentioned it an hour into the dinner. Didn’t believe it was a real thing, I got it and so did my entire family including my immuno compromised mom who ended up hospitalized for Christmas.
#11
Brought a friend to dinner. Ok, sure bring a buddy I suppose. But the friend wanted to sit at the table and not the bar so we could have some privacy. And they both thought I was going to pay for dinner for all of us AND drinks! And friend made it clear she was only there because her friend like to sleep with guys and she was there to prevent that. I kind of felt like I was being accused of a crime!
I just looked them both in the eye, told em, "I ain't the one." and left. This was before we even got our drinks too.
#12
We had previously agreed on a restaurant, time and to just do separate bills, to which I would offer to pick up hers at the end to be polite. I arrived on time and msg'd that I was there. I got a reply stating she was already inside and seated. The server had just bought her another glass of wine and was walking away with an empty wine glass and a shot glass. The first words out of her mouth weren't even hello, they were "you're paying, right? I don't have any money". I didn't breathe a word. I just turned around and left.
#13
I tried online dating once. I was basically tired of being lonely and wanted to see if I could fond someone who I might end up starting a life with.
Went through the app and found a beautiful woman who I matched with. We started talking and our conversations would last awhile, usually an hour +.
Anywho fast forward to date night, keep in mind by date night we had been talking over a week, some random woman walked up to me and said "hi are you blank?" and I was like ya, who are you?
It was my date, who used her friends picture asher profile pic.... I was stunned. She however was incredibly upset when I looked at her and ask why she had lied. She wasn't ugly by any means, but she wasn't honest from the start.
She started crying when I told her that I was sorry but I don't think we should try to date because she lied and I couldn't trust her. But that's my worst date. Nothing terrible but still a bad date.
#14
While driving us to dinner, my phone (on vibrate) went off in my pocket. I look at the text and it is from my date sent to me accidentally saying 'oh my God he's so ugly'. I pull over to the gas station, hand her $2 to run in and get some lottery tickets and I drove the F off.
#15
She literally asked what was their most expensive drink. The waiter met my eyes and the bro code kicked in. He just kept saying everything was out of stock. God bless him where he is now. I went back to give him a tip but he declined.
#17
First time meeting. During the drive I saw my address already in her Google maps. She told me about how she use to follow me to the store after the gym to see if I had any "kids". During dinner I told her that I went to go talk to the chef for vegan options and left.
#18
From the second I picked her up until I abruptly ended the date she was on her phone. Mind you, I’m a tech nut will use my phone A LOT…however, on a date when trying to get to know someone, no. She asked where we were going, and after I told her she was on Yelp, Facebook, checking Google Reviews. Then, when we get there, she needed to check in on Facebook, take a selfie for Instagram(which she asked me for my username so she could tag me), took a quick video for her Snapchat(again, asked my username to tag me). And, once inside…we took a “couples” selfie. Then, she snapped photos of the menu, took one of those “in reverse” videos of her tearing apart a piece of bread. She asked me to get a shot of her holding her plate(which had a steak on it) for comparison to her head size. It’s was selfies here, videos there, tagging this, dropping reviews mid meal! I had enough. I politely asked her if she could get herself a ride back to her place…she was blown away, but said she could score an Uber. I hung out until said Uber arrived. This allowed me some time to ask why all the social media stuff during a date. “I just need to let people know what’s going on!” Yeah. As much as I kind of get that…not on a first date. Her ride got there, she left, I paid…I left. Didn’t talk to her at all after. However, I have an insane feeling there were Snapchats, Instagrams, and Facebook posts about me.
#19
Right before I went out with her, I checked her Twitter and she was live tweeting everything. Her getting ready, her coming to meet me, etc. The entire date she was like always typing on her phone, and alas, she was live tweeting the entire thing. At this point the date was over in my mind, but I just purposely made it entirely weird to see what she’d tweet. By the time we finished our dinner and drinks I had made it so uncomfortably awkward and he tweets were just hilarious. We got up and walked outside and I was like “I guess there is no shot at a second date” and she was like “what do you mean?”, and I replied “Well you tweet led 17 minutes ago that you’re definitely not going out with this guy again” and she just got wide eyed. I told her that within 5 minutes of the date she had tweeted three times and it was incredibly disrespectful for me, so I made it the worst date possible on purpose. She tried to apologize which I accepted, but I didn’t want to see her again, and told her to leave her phone in her pocket on the next date she goes on.
Ever since then, I either leave my phone in my car, my pocket, or in my girlfriends purse. I can’t tell you how much better dates are when you both leave your phones away.
#20
I had one throw a huge fit because I paid with a gift card, she got up and walked out saying a real man pays with cash. She left her leftover steak, that she only had like 2 bites of so I was okay with that.
#21
She ate food off my plate. I'm not talking about stealing a fry either. She nearly ate everything. Ladies, this isn't cute.
#22
I said I'd pay. She offered to pay half. I took her up on it. This was apparently the wrong choice.
#25
I guess not the worst thing but I took a girl out on a first date where she ended up getting wasted at dinner and pulled her [chest] out of her dress and kept them out thinking it was hilarious. We ended up getting kicked out of the restaurant.
#26
She took me to her place and we [slept together]... after repeating that a few more times, she accidentally mentions that she has a husband...
Then classic story about him being [toxic] and them being near divorce... years later - they're still married...
#27
Only talk about her ex, and the break up, talking in details about all of it, and refuse to change the subject.
The best part is, the break up happened when she was 22, she's 35 now.
Fun times that was...
#29
We had ordered drinks and an appetizer after she picked one of the most expensive restaurants in town. She took a few sips, and then asked me about my job. I explained a little bit about it, said it was pretty boring unless you are a software/firmware/network nerd, and asked her about her.
She asks "Does it pay well?" I kinda agree and then try a second time to change subject.
She says "I'm asking you how much you make, because I don't want to waste my time on someone who is broke."
I tell her that it's complicated, because when you get to a certain level at a company, you become a flight risk, but also a risk to their long-term strategy as you are considered a strategic asset. So they won't overpay you, but your salary is basically "name your price."
She says "Do you make more than $250k a year or not."
That's when I knew it was unsalvageable; she was not just tactless, but rude as well. Also, she would invariably be the type of person to think they should spend all the money as fast as they could.
I looked her in the eyes and said "Image thinking $250k a year is a lot of money," paid for the food, tipped stupidly, and left. It was the only date where I felt like I couldn't continue it.
#30
I don’t have any total horror stories but when I was away at school (like two hours away from home) I matched with a girl from my hometown when visiting my parents. We talked for a few days and she wanted to meet for dinner but I had already gone back to school and it was the middle of the week. So I skipped a n evening lecture to go see this girl (as a 19 year olds this seemed like a good idea), and drove two hours in the dark and snow.
Got to the restaurant and when I went to message her that I was there I found she had deleted me from everything. I texted her (we didn’t text often but I had her number) and got no response. Still have no idea why she did this but she was well aware I was driving two hours to meet her. The Last message she sent me was AFTER I told her I was leaving, telling me to drive safe. Not sure what changed during the two hours I was in the car but I never heard from her again.
Needless to say My parents got a surprise visit from me that night and I didn’t feel like telling them why.
#32
Told me I had 12 months to propose.
I proposed - that we get the bill because I had to wash my dog's hair.
#33
Pretend it was a date in the first place, we went to a Texas Rangers game, turns out she was just using me to take her on a “date” so she could post pics and make her boyfriend jealous, I didn’t know she had a boyfriend by the way.
#34
Burst out in tears that she was still in love with her married ex-BF who broke up with her to go back to his wife and kids when I asked if she had dated anyone recently.
Cost me two drinks at the bar, but saved a lot of heartache and left no chance for a second one.
#35
*cracks fingers*
Met a girl online, hit it off agreed to meet, we lived on opposite ends of a major city, she was more familiar with the city then me and insisted on picking a restaurant that was “halfway” between us, she insisted on meeting at 6 pm on a weekday, I asked for a later time to avoid traffic, but she insisted, I left 3 hours early to get there on time, I realized about 2.5 hours early that I’d probably be five minutes late, sent her a text and apologized, no response, got to the restaurant, she seemed nice, told me she didn’t drink alcohol (which was fine I was a very social drinker and still am) and insisted that we couldn’t order our own things we had to split everything, ok…kinda weird but I guess this means I get to try more things on the menu.
Halfway through the date mid conversation she tells me “so I hope you realize that at this point I expect you to fight for me” I have a puzzled look and ask “…what?” She tells me that “we’ll there were times I would initiate conversation or plans and I won’t do that anymore as the man I expect you to take the lead and initiate everything from here on out.” I didn’t really know what to say and changed the topic.
Dessert came, she ordered some cookie thing, insisted that it had to be warmed up (even tho they didn’t serve it that way) sent it back when it wasn’t warm enough (they def messed with it, I mean I would’ve), bill came, I paid, and we went to leave, I had a two hour drive back so I was ready to get on my way home, she asks if I want to do anything else by this point it was like 9ish on a weekday.
I was admittedly a little pissed off by this whole waste of my time and said “what would you possibly expect to do? You don’t drink and most other activities are closed plus I have a two hour drive home”
“You have to drive two hours back?” She said.
“Yeah don’t you? You said this place was halfway.”
“Oh no” she said “I live about three blocks that way I walked here.”
The next day she text me about how much fun she had and how she couldn’t wait to do it again….
#36
She belittled my interests. I mean, if I can pretend I care your dumb collection of perfumes you can at least pretend you care about my passion for mechanical keyboards.
#37
She almost got into a fist fight with the server bc she thought I only took her out to flirt with anyone else, since she was so enthralled in her phone I just had conversation with the server and I guess she didn't jive with it.
I apologized profusely, and paid for the full bill ( I should've only paid for my stuff ) and I left the server a huge tip. I wanted to ask her out but she was wearing a ring so I was afraid to tempt it and embarrass myself.
I pretended to order her an uber and gave her bogus info and drove off. As gorgeous as she was, she was such a waste of time. It's so disappointing when that happens.
#38
Make a joke about how she would grab a pan and smash it over my head if I pissed her off even slightly. Blocked her phone number on my way to the car after dinner.
#39
Negatively compared me to an ex and gush about how great he was. Without being prompted.
I would take fault if it were mine, but I had literally stepped out of my car when meeting her, and she was trying to say her ex had a nicer car almost immediately. This went on for the next hour or so.
I was wondering if I had done something to piss her off prior to ever meeting her, like cut her in line at the grocery store or not held the elevator door open for her or something. Seriously, it felt like it was just a spite-fest to tell me how I didn't stack up next to her exes, how my choice in drinks wasn't to her liking, even criticizing my drink choice.
At the end, she told me she had a great time. She unmatched me though within like 30 minutes, no explanation (and none was needed.) I can't help but think this was some kind of hit or bad karma for something I probably did somewhere else to someone else, but I honestly can't think what it would be.
#41
It would have to be a tie between the one who wanted to go to a ball game and ended up ditching me and leaving with another guy and the one a few years later who wanted to go to a party and proceeded to get totally smashed, puked, passed out, and I had to carry her to her apartment.
Didn't call either of them again and wouldn't have even if they'd been a sure thing second-date lay.
#42
Tl;Dr: She showed up to the date with a baby she didn't tell me about & used me for a free meal.
I gave her my number at the grocery store she worked after about a month of flirting while she checked my groceries. She was attractive and made great conversation. We talked on the phone and text for a couple weeks before our schedules lined up to go out.
We met at a restaurant, she brought a baby that she didn't tell me she had. No problem I can handle that if the situation is right, but red flag. Didn't bother to even brush her hair. No problem, she had a baby and a job, I get it... but red flag. Didn't say anything about "yeah surprise I got a baby and I couldn't get myself presentable". Ok she was embarrassed or whatever, that's fine. Red flag.
What made all that not fine was half way through she changed the baby at the table. There was a changing station in the men's room so I could assume there was also one in the ladies room. On top of it all she didn't really say much and was looking around while I was talking to her and wasn't very talkative. Only saying enough to answer my questions without elaborating.
I asked for the check when I'd seen enough and she said "thanks for the meal," got up and left before the check came.
Looking back now, she probably did this every week to get a good meal and ensured it didn't go further with the red flags. In the future, if a girl shows up with a baby that she didn't mention before I'll give her $10 to pay for part of her meal (I was raised a gentleman) and tell her "deuces, biotch".
I can handle a girl with kids, but don't surprise me with them.
#43
Told me she was not attracted to me at all and that she was a lesbian who just wanted to experiment to see if she could "get over it".
#44
My date asked me to come to her place. Once I was there she told me to assemble her sofa. I was dumb enough to do it and then she kicked me out. Then (and many more events) sent me on a pickup artist journey.
#45
Showing up to the bar seven hours early and proceeding to get blackout drunk while repeatedly texting me throughout my work day saying I should "just come now" is the first thing that comes to mind...
#46
Nothing. Absolutely nothing.
I met a girl via a dating app, wasn't instant sparks or anything but she seemed nice enough and we had some shared interests, so I invited her out for dinner and she accepted.
She showed up to the date looking like she'd rolled out of bed - sweatpants, a plain t-shirt, zero makeup. I'm not someone who thinks a first date needs to be all dressed up and formal, but it was clear she had put zero effort into her appearance.
We sit down to eat and she absolutely refuses to engage in the conversaion. Every question I asked got a 1 or 2 word answer with zero followup.
"Have you ever been to this restaurant before?"
"No."
"How's your week going?"
"Fine."
"I saw on your profile you coach little league softball, that must be a lot of fun."
"It's okay."
The. Entire. Time. It was *painful*.
I finished my meal quickly, walked her to her car, thanked her for her time and left. Later that night she sent a text saying "I had fun tonight". I figured she was just being polite so I didn't respond.
The next morning I woke up to a text with MULTIPLE PARAGRAPHS from her calling me a jerk for "ghosting" her and saying how if I wasn't interested in seeing her I should be up front and say so. It was, and I'm not exaggerating, several times as many words as she'd spoken the entire date.
To this day I'm perplexed by the whole thing. All I can figure is maybe she was really anxious or something on the date? It was bizarre.
#47
Bragged about stealing, (yes literally stealing behind his back) her last boyfriends gucci watch. Then proceeded to complain about her last date for being "too fat", then geniunely got offended I had an android phone instead of an apple. Real nice person.
#48
Alright, I was talking to this girl for a while online and we were hitting it off great, common interests, can't stop talking, all the cutesy stuff.
We set up a meet to chill at my place, I'm sitting there all excited bc I'm gon get some cat. I get a text, she here; I RUN outside to see a big pickup truck, her in the backseat, and her PARENTS IN THE FRONT.
Yall, I was 23 at the time and just kind of looked at them, her dad leans out the window and goes "You know she's 17 right? Like, it's fine but you're the legal adult for a bit so don't let her get into nothing."
BRO WHAT.
Deleted/blocked her on everything, and about a month later got a snap from her along with a picture of my house talkin bout "It's my birthday, we can be together now."
So, yeah, I stopped talking to strangers on the internet after that.
#49
Told her I wanted to use my law degree to help out with humanitarian purposes. She proceeded to go on a rant about how Syrian immigrants were worse than the rats in her country.
Left promptly during her bathroom break.
#50
She brought 2 of her friends. It was weird. She made no mention of it at all prior to meeting up.
#51
Took her out. She kept asking a lot of family law questions. Like...a lot. Pretty much whole date. Dropped her off. She said she liked me but she's couple months pregnant, could never afford an attorney and thanked me for all the advice.
#53
Ask to move the lunch date ahead 2 hours then admits she isn't going to make it because she drank too much the night before. She's a 37F & wants to get married and have kids, like now.
#54
She smoked about a pack of cigarettes during the date, while I don't smoke.
She asked me "does it bother you, if I smoke?"
I thought she'll smoke 4-5 max, not a whole pack.
#56
We had a pretty nice dinner, and she said she was meeting friends after. Which is pretty normal to have an endpoint built in. But then when dinner was up she invited me to go with to meet her friends, which I took as a really good sign she was having a good time and I thought it would probably be fun. Why not? She didn't speak one word to me the entire time we were there. So awkward. I never called again after that so I'll never know why she bothered to invited me.
#59
Lie. Then lie to others about what happened on that date.
Nothing bad happened btw, but we were young and she was a co-worker. Another co-worker told me she pulled the same thing on him as well. Looking back on it, I'm pretty sure she was a textbook pathological liar.
#60
Rolled her eyes over the idea that I researched where to take her on a date. It was a cafe with a harpist. That was magical.
#62
Where do I begin.
Within 5 minutes she told me she just broke off an engagement.
10 min later she said she went out with a guy the previous week, hit it off with him, but then when he went to the bathroom she left the bar with another guy in a cab.
Told me to buy her drinks. Said I’d be sitting at the table while she’s in the bathroom.
I look up 10 min later and she’s talking to the bartender drinking.
Asked her what’s up? She said she didn’t see me. I drank “her” beer and left.
Texted her that I had a great time sarcastically and said she wanted to meet up again. Wacko.
#63
A tinder match once invited me out to meet with her and some friends at a bar.
When I got there she was making out with some other guy, worst of all she tried to deny it!
#64
I once went on a date with a girl who I swear had absolutely nothing going on between the ears. She was good looking/cute in the way I like, but my God… it was like carrying on a conversation with a naive rock.
#65
Was in the bathroom a long time. She was going through my medicine cabinet, checking labels.
#66
This isn't terrible as much as it was very strange.
I'm from upstate NY, she was from Florida. She had made several questionably accurate statements through out the night but I finally said something when she claimed lacrosse originated from Florida. It's pretty well established it came from the Iroquois tribes of western/central NY.
She proceeded to open Wikipedia and read the entry while inserting Florida throughout in an attempt to prove her point.
I dropped it but checked when I went home and she was just openly lying.
#67
- Told me I shouldn't let others know I'm in therapy (I was a bit late to the date due to this)
- then told me she's technically still married, but she ran from her [toxic] husband (wanted to call things here but we were at my favorite pizza joint)
- is very drunk as she has been there a few hours. Picks a fight with the table next to us
- leaves to go smoke for 30 minutes
- tries sticking me with a $200 bill racked up by her and a friend of hers.
Paid for my pizza and got the [hell] out of there after apologizing to the table next to me.
#68
While out watching a movie, some guys came into the theater to sit down and the girl I went on a date got up and left without saying a word. just left me sitting there alone in a theater because she didn’t want some guy she liked to see she was out with me.
#70
Berated me for having a son. I shared it with her to be honest and she told me I was beneath her.
She was divorced. God bless her ex.
#72
Flashed the bartender repeatedly until he threatened to kick us out. Grabbed the cab driver's phone and threw it out the window. I had her dropped off and she took another cab back to my house at 2am and yelled "HEY BUDDY GUY!!" in the yard because she couldn't remember my name.
#73
Got food/drinks, had a good time. Got an uber to go ice skating. Made out a bit on the drive over. She asked me to take a picture of her ice skating, which I did. While still on the date she updated her Tinder profile with said picture.
#74
Went on a date with this girl & she drank half her drink, spilled it on purpose just to get another free one. Then she ate half her meal & told the waitress that she didn't like it & had to speak to manager..she got a free dessert from that. Just embarrassing, First & last date!
#75
Eat with mouth open. It was like getting a close up shot of a garbage disposal.
Not that I am royalty, but I thought that I’d never be able to bring her a friend’s house for dinner.
#76
Called me “Dude”. Like repeatedly. Downvote me to hell but I cannot stand when a girl I’m romantically interested in calls me Dude.
#77
She looked nothing like her photos, invited me back to her place which looked it hadn't seen a cleaning product since it was built, did blowtorch dabs for 20 minutes before acting like it was time for me to take her to bed. I said I needed something from my car and left. She still texted the next day asking when date 2 would be.
#78
She spent the entire time talking about Julia Roberts. Like it was brought up so much, like half the night was spent discussing her love for Julia Roberts. I was neutral on Julia Roberts at that point, but after the date I didn't like her out of spite. Sheeeeeeeesh.
#79
She told me to pay for the meal, as a way of repaying her for her time spent applying makeup. She asked for the date.
#80
Mine was a meet up at a bar following some tinder chats. She turns up considerably heavier than her pics. No issue, carry on the date and have a couple of drinks. She then proceeded (without my knowledge) to invite about 10 of her friends to the bar and she’s there holding my arm and cuddling in and trying to get kisses etc and acting like we’ve been dating for months. It was very awkward. I ended up making a getaway - only after she demanded a kiss.
#81
She wanted to go to several different places to experience things and clearly didn't want to pay. We went on about six rounds. We grabbed an appetizer at one place, dinner at the next, a drink at another, ice cream here, another drink there, etc. The last place we had pricey cocktails ($40/ each) and the bill was put in front of her. She slid the bill over to me with one finger.
She transformed in front of my eyes. She went from this extremely attractive, slightly older woman to just this unattractive person. She wanted to do something after, which I found out later was to go home with me. I was so turned off that we just called it a night.
I decided to end it her after that but she wanted to go out again. I politely declined. She kept trying to re-engage though. I happened to have met my wife a few weeks later and we got pretty serious. When she found out, she never talked to me again. Problem solved.
#82
She asked if she could give my left overs to her baby daddy cause he was watching the kids while she was out.
#83
She told me she had girlfriend and two kids and was still movin like them two didn’t exist.
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