When you think about it, going on a date with someone is the ultimate adventure. If the two of you have never met, you’re essentially sitting down with a total stranger and hoping for a spark (or at least, an interesting conversation) when, in reality, they might be the complete opposite of you and laugh at everything that’s dear to you.
And even if you know each other beforehand, expectations can still get in the way and make the night very awkward. It’s easy to play cool board games in a fun friend group, but an honest one-on-one under dim lights? That’s a whole different world. There are a million reasons why it might go wrong!
So to give you a sense of what might happen if you’re putting yourself out there—and reassure you that in certain scenarios, taking off is perfectly justifiable—we’ve gathered some of the worst first date stories we could find on the internet.
#21

Met someone for a lunch date, and it went fairly well, but on the way back to our vehicles, she told me she loved me, and made it a point to mention that she was on the pill, so I had the “green light.” I told her, “I don’t think I should see you again, as I feel very uncomfortable.” She started crying hysterically, and told me she could get someone tomorrow who will take care of her.
More power to you, I just hope someone else listened to the head on their shoulders like I did!!!
More power to you, I just hope someone else listened to the head on their shoulders like I did!!!
22points
#22

This happened about 10 years ago. TangoWire was this website that had many different dating sites. I matched with this amazing military man who had tons of pictures and was willing to meet after we exchanged numbers and texted for 2 days straight. He sent me pictures of him in uniform and we decided to meet at a Starbucks that was midway for both. Said he was wearing a black tshirt, white pants and would be holding a red rose in front of the entrance. Now this military mans picture showed he was 6’3, Caucasian and built like a truck. What was waiting for me was a 5ft Asian man with a black tshirt, white pants and holding a red rose, looking around waiting...I drove past, went home, blocked his number and deleted my profile.
21points
#23

Was invited over to her home. Upon entering in, the whole house was dark. When we came inside she told me to “be quite.” As she guided me inside her home (in the dark) i heard a male voice and saw a male toss blankets from the couch. He said “wth.” He was angry. I didn’t know who he was but he was clearly UPSET. She locked me in her room. I could hear arguing in the house. It turns out her ex lived with her. The ex wanted to “come at me” and “fight me.” I left the house. The cops were called (they were approaching as i was leaving.) Best. date. ever.
20points
#24

I went on a date with a guy who was friends with a guy I worked with. I guess he came through my line but I couldn't remember him, so I looked him up on Facebook. All group photos, I couldn't tell which one was him but agreed to go on a date with him. Our date was walking around wal-mart while he got some stuff he needed for a camping trip. He talked about himself a lot and I wasn't attracted at all but i thought I would give it a chance. He also bragged to everyone about being in the navy but he was medically discharged before he made it to basic training. A few days later he came to my work and was wanting me to kiss him in public and got upset when I told him that made me uncomfortable, and he was really argumentative for someone I literally just met.
I cut him loose after that. The real kicker was that a year later he got caught in a sting operation for trying to meet up with what he thought was a 14 year old boy. So yeah I went on a date with a child predator :(.
I cut him loose after that. The real kicker was that a year later he got caught in a sting operation for trying to meet up with what he thought was a 14 year old boy. So yeah I went on a date with a child predator :(.
19points
#25

I went on a date with a guy I had been messaging for about. Week or so.
We met at a nice little restaurant, had a pleasant dinner, and then we went to a Wine Bar and that’s when it went downhill.
It was super loud to the point that I couldn’t hear anything he was saying, I was standing against a wall because of a lack of seating,
He proceeds to stand in front of me, and kiss me and it wasn’t good kisses, they were sloppy and cringy.
After about 5-10 mins of that, I excused myself and said I was really tired and needed to go home.
I didn’t hear from him for a while and forgot about the whole ordeal.
He messages me back a few months later, telling me he’s not interested. (As if I care)
He proceeded to tell me how his daughter who is adult age can sleep with anyone she wants and starts discussing her intimate life.
I was stunned and completely grossed out that he’d talk about his daughters personal life in that way.
We met at a nice little restaurant, had a pleasant dinner, and then we went to a Wine Bar and that’s when it went downhill.
It was super loud to the point that I couldn’t hear anything he was saying, I was standing against a wall because of a lack of seating,
He proceeds to stand in front of me, and kiss me and it wasn’t good kisses, they were sloppy and cringy.
After about 5-10 mins of that, I excused myself and said I was really tired and needed to go home.
I didn’t hear from him for a while and forgot about the whole ordeal.
He messages me back a few months later, telling me he’s not interested. (As if I care)
He proceeded to tell me how his daughter who is adult age can sleep with anyone she wants and starts discussing her intimate life.
I was stunned and completely grossed out that he’d talk about his daughters personal life in that way.
18points
#26

Went on a date with a guy who refused to talk. I would ask him questions to start conversation & he would give a one-word answer and then go silent. After awhile I gave up on trying to talk to him so we ate our meal in complete silence. At one point I started laughing (nervous/uncomfortable thing) and he didn't even ask me why I randomly burst into laughter. He drove me to my apartment in complete silence as well. Basically a solid hour of no speaking.
17points
#27

In high school a guy asked me out. It started great, he showed up with flowers and opened my car door for me. Then on the way to dinner every time he hit a red light he would lean over and stick his WHOLE TONGUE in my mouth (I was too young to feel comfortable saying wth). We get to the restaurant and I tell him that I’m severely allergic to shellfish and peanuts lol. He proceeds to order shrimp skewers and ask if I want some (aweh considerate! Lol). Spent the ENTIRE time watching the football game behind my head and not listening to what I was saying at all. When it was time for dessert he grabbed the menu and said “I got this, I know the BEST thing here!” And I reminded him I was allergic to nuts and he goes “oh yea... well you better pick then” he was going to choose a peanut butter sundae. Did I mention the restaurant he took me to was the place he worked? He honestly spent more time talking/listening to our waitress than me.
17points
#28

First 2-3 minutes he told me about his DUI and then laughed at me that I lived with my parents (at the time age 30).
17points
#29

Not me, but my housemate. A few weeks ago she had a date planned with a guy for dinner and he kept pushing back the time cause he was “busy” (idk the exact details). Well it came close to Midnight and he messaged her saying that he still wanted to go on a date with her and then proceeded to pick her up. Since it was midnight, nothing was open... except for gas stations and he was thirsty. So they proceeded to drive to a gas station where he went in and got himself a drink while my housemate stayed in the car. He did offer to get her something but she didn’t want anything. Afterwards, he brought her home.
TLDR; My housemate went to the gas station for a date after midnight.
TLDR; My housemate went to the gas station for a date after midnight.
16points
#30

The guy showed up half an hour late in an arm cast. He ordered a steak where he asked me to cut it up for him. Throughout dinner, all he talked about was himself and complained about his job. Afterwards, he asked me to drive him to his car which was only a few blocks away. Tried to kiss me at the end of the date and when I gave him the cheek, he called me selfish.
The next day he asked for a second date. I blocked him.
The next day he asked for a second date. I blocked him.
14points
#31

Started talking a to a guy off Tinder. We chatted for a good week before we were able to meet (he was divorced, has young kids, etc.) Anywho, we decide to meet at a bar/restaurant in a Wednesday evening. Keep in mind, were both mid-late 30's, work full time, etc.
So, he's late, like almost 30 minutes late. Apologizes and proceeds to order a beer and a shot of fireball. Asks if I would like one. I hesitate but say, "sure, I'll have one with you." So we're chatting, having a good time but dammit, he's talking a mile a minute, constantly interrupting me and complimenting me (thank you but, let me tell my story).
Long story short, he proceeds to order at least 5 more beers, I think 3 shots. I had 2 beers and the one he had offered me. I suggest we order food so we order a couple of burgers.
After this, he orders ANOTHER shot of fireball and a beer and by now it's about 9:30, I want to get home and get ready for bed. We go to leave and our waitress comes running out, worried about him driving. He claims he is just fine, has a high tolerance, didn't drink that much, etc. I tell him maybe he should order a lyft/uber and again he claims he is fine but he wants to come home with me.
I politely decline and state I have to work early the next morning. He gets all weepy, tries to kiss me and I excuse myself and tell him maybe next time. Never heard from him again!
Another one - met a paramedic coming off of his shift. Good-looking man, divorced, couple of kids. We're eating our meal and he proceeds to start on about his ex-wife and how horrible she is, complains about how much he pays for child support and how he would "really like to hire someone to take care of her." Conversation was pretty lacking after that. I felt a bit uncomfortable and just stated how sorry I was that he was going through that. We finished our meal and we parted ways. Again, never heard from him either.
So, he's late, like almost 30 minutes late. Apologizes and proceeds to order a beer and a shot of fireball. Asks if I would like one. I hesitate but say, "sure, I'll have one with you." So we're chatting, having a good time but dammit, he's talking a mile a minute, constantly interrupting me and complimenting me (thank you but, let me tell my story).
Long story short, he proceeds to order at least 5 more beers, I think 3 shots. I had 2 beers and the one he had offered me. I suggest we order food so we order a couple of burgers.
After this, he orders ANOTHER shot of fireball and a beer and by now it's about 9:30, I want to get home and get ready for bed. We go to leave and our waitress comes running out, worried about him driving. He claims he is just fine, has a high tolerance, didn't drink that much, etc. I tell him maybe he should order a lyft/uber and again he claims he is fine but he wants to come home with me.
I politely decline and state I have to work early the next morning. He gets all weepy, tries to kiss me and I excuse myself and tell him maybe next time. Never heard from him again!
Another one - met a paramedic coming off of his shift. Good-looking man, divorced, couple of kids. We're eating our meal and he proceeds to start on about his ex-wife and how horrible she is, complains about how much he pays for child support and how he would "really like to hire someone to take care of her." Conversation was pretty lacking after that. I felt a bit uncomfortable and just stated how sorry I was that he was going through that. We finished our meal and we parted ways. Again, never heard from him either.
14points
#32

Turns out he, at the age of 22, was married in a polygamous relationship. And had slept with 140 partners.
13points
#33

Went on a tinder date (really just met up while at a bar, both of us with friends) with this guy. Was nice enough until I took him, my friend and his friend to their house, where on the ride over maybe two blocks from his house he got in a yelling match with his friend over a misunderstanding and literally asked me to stop the car so he could storm off. We found him in a shop eating noodles a few min later, and as I was trying to get our date back on the right track, a girl walked in and told me “you guys can go to his house now, his gf just left.” What a hot mess.
12points
#34
Similar situation... went out for coffee with a guy I matched with on Bumble. Not only was he 30 min late with zero communication (I was playing on my phone and enjoying my coffee so I didn’t notice how late he was), he sat down, didn’t order anything, didn’t introduce himself, and just started talking. 30 min in I was casually texting my safe calls to call me and tell me my kiddo needed me home. Of course nobody was available so I ended up stuck in a 3 hour conversation where I said basically nothing. By 60 min in he was telling me how much I would like his mom. I couldn’t think of a polite way to get myself out of there and was sort of frozen when an employee came up to tell us they were closing soon. I jumped up and said all the nice platitudes and went to leave because he had come in a different door than me so we weren’t parked close. Nope. He insisted on being a “gentleman” and escorting me to my car, despite my protestations that it wasn’t necessary. Dimly lit parking lot, empty, dude who doesn’t understand social cues... I tried to just get in my car, he held the door and asked for a hug, I tried to give him one quickly and get back in and he kissed me, I had to actually push him off me because he wouldn’t let go. He was frowning and said “is that it? Seriously?” And I left. Blocked him. Have not gone on a first date since. It made me realize that despite my extracurricular activities, I managed to forget vanilla meetings can be dangerous too.
TL;DR awful first date, self-absorbed conversation, unwanted physical contact, reminder that dating requires CONSTANT VIGILANCE.
TL;DR awful first date, self-absorbed conversation, unwanted physical contact, reminder that dating requires CONSTANT VIGILANCE.
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12points
#35
I went out with this one guy, and I thought we were hitting it off, and all of a sudden he starts saying the N-word like a million times (to clarify, both of us are white). He justified it by saying that he had black friends that allowed him to say it. I kept hinting that I really didn't like him saying that word, but it didn't take.
Before we ended up leaving, a group of Indian people came in and he made some comment about 'these darn Hindus' and I was in shock.
Definitely wish I'd been more outspoken about how bad the things he was saying were. But did not see or talk to him again.
Before we ended up leaving, a group of Indian people came in and he made some comment about 'these darn Hindus' and I was in shock.
Definitely wish I'd been more outspoken about how bad the things he was saying were. But did not see or talk to him again.
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11points
#36
So this dude (Im a F) I met 2(?) years ago. He became super attached after swiping, which wasn’t too odd, but def sent a flag. He mentioned at some point how he couldn’t stand women who filtered photos. Mind you. All, but maybe one I noticed, were filtered; he also told me he was 5 years older than the date on his profile.
Mind you, non of my photos have filters, but I had makeup on (foundation and eyeliner on my top lid), and was dressed in nice clothes (I teach fitness classes, leggings and a bun are a daily)
I was reluctant to meet him because he was coming on so strong; sent me a shirtless photo without asking, and was just so upset that I was going on other dates with dudes. But I didn’t want to be mean and said ok let’s meet after I’m done teaching. I also reminded him I just finished class, I look like a hot mess, and he said he didn’t care.
So I meet him at the restaurant, he talks about filters women use on apps, looks in literal pain, says he needs to take this call from his friend...and yup...he left.
I didn’t care since I was able to have my favorite salad, thought it was hilarious he was so concerned about looks. And honestly I look like my pics anyway, but I was just so happy I didn’t have to ever text him again.. I hope he found his happiness.
Mind you, non of my photos have filters, but I had makeup on (foundation and eyeliner on my top lid), and was dressed in nice clothes (I teach fitness classes, leggings and a bun are a daily)
I was reluctant to meet him because he was coming on so strong; sent me a shirtless photo without asking, and was just so upset that I was going on other dates with dudes. But I didn’t want to be mean and said ok let’s meet after I’m done teaching. I also reminded him I just finished class, I look like a hot mess, and he said he didn’t care.
So I meet him at the restaurant, he talks about filters women use on apps, looks in literal pain, says he needs to take this call from his friend...and yup...he left.
I didn’t care since I was able to have my favorite salad, thought it was hilarious he was so concerned about looks. And honestly I look like my pics anyway, but I was just so happy I didn’t have to ever text him again.. I hope he found his happiness.
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10points
#37
I met a guy from Bumble. We met up at a Starbucks and he talked nonstop about himself for 2 hours... I barely got to say a few sentences that entire time. I didn’t even get to order anything to drink because I felt bad to interrupt him. He didn’t even get up or order any coffee for himself. So I felt stuck sitting there and listening to this man. I wondered how he was able to speak for 2 hours without having anything to drink, he must’ve been really thirsty afterward lol. Also, he was a lot shorter in person. He put in his profile that he was 5’8” when in reality he was probably 5’4”.
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10points
#38
I went on a date with this guy whose teeth were so gross (pics online hid them...never again) and he kept smiling throughout the date so I just wanted to talk about sad/serious stuff so he would stop smiling.
I made up an excuse to go home and I called an Uber. I had the Uber drive around the block and drop me back off at the bar once he was gone. I ended up hanging out all night with some people I had struck up a conversation with at the bar while I was on the date.
I made up an excuse to go home and I called an Uber. I had the Uber drive around the block and drop me back off at the bar once he was gone. I ended up hanging out all night with some people I had struck up a conversation with at the bar while I was on the date.
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8points
#39
Met a guy on match... dinner was good then he dropped me off at home and drove home. It was raining... and he got his fancy BMW stuck in the mud in backroads of Kansas after being diverted due to a closed highway for a wreck. He called me crying because he had a flat, so I went to rescue him. Only to have his phone run out of battery so I couldn’t find him. I called the police to help me find him... but no luck. By the time I got home, he was sitting on my porch crying and covered in mud. There wasn’t a second date.
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8points
#40

This is the first and only interview date I had.
Friendly enough girl but we had ZERO chemistry. She was rather boring, never been in a relationship and was an accountant at a plate factory. To be fair to her, I just got back into dating after finally getting over a bad breakup so my skills were eroded.
Our conversation during dinner stunk. Every answer we gave was straight to the point like we were on a timed debate.
Friendly enough girl but we had ZERO chemistry. She was rather boring, never been in a relationship and was an accountant at a plate factory. To be fair to her, I just got back into dating after finally getting over a bad breakup so my skills were eroded.
Our conversation during dinner stunk. Every answer we gave was straight to the point like we were on a timed debate.
7points




