There are few things more embarrassing or awkward than a bad first date. Maybe you're the kind of person to give people a second chance, but for many folks the first impression is everything! Instead of experiencing some awkwardness firsthand, skip the trouble and just read these stories of people's terrible dates.
“Met this girl through tinder, she was from the east coast and I live in the west coast. We meet up and she explains to me that she never had the need to drive in the east coast because public transportation is way easier over there than it is here. She then went on and told me that she really wants to learn how to drive but doesn’t have anyone to show her let alone a car to learn how to drive on. At the end of the date I (stupidly) offered my car for her to at least have a taste of what it’s like to drive a car. Long story short, I told her what to do and the second she took her foot off the break she panicked when the car started slowly rolling on its own and then slammed into the parked car that was in front of us. I left a note on the other car and never heard from the girl again.”
A Very Strange Encounter
“When I was a grad student I was a regular at a cafe near my home. Down the street from the cafe were a few retail shops behind glass windows. I used to walk by them on the way to the cafe. One shop wasn’t particularly busy and as I walked by I would always make eye contact with the girl who worked in the shop and give her a smile.
One day she came into the coffee shop. It was busy, so I invited her to sit with me. We talked a bit, exchanged names, and had a nice time for the ten or fifteen minutes we sat together. A few days later, she saw me walking by her shop and she came out of the shop to give me her number.
I called her that evening and we talked on the phone for hours. I kept trying to get off the phone, but she was a great conversationalist and kept the conversation going. It was fun. I don’t think I had ever spent so much time on the phone. Before we finally hung up, we arranged to go on our first date.
Friday night and I pick her up at work. She was like fifteen minutes late, which was no big deal, but she was really apologetic. On the way to the restaurant, I try to make conversation, but she is mono-syllabic. At the restaurant, the ‘conversation’ was punctuated with long silences. After one of the silences, she suddenly blurts out, ‘I’m fat. I look like I’m pregnant.’ I was taken aback and didn’t really know how to respond to this. I thought she looked great, but my only response was, ‘Why do you say that? It’s totally not true.’ More silence ensued.
The drive home was mostly silent but met with another out-of-the-blue comment. She said, ‘I don’t think I could date someone who isn’t close with their parents.’ It sounded like an accusation. I didn’t know what to say to this. My parents and I are quite close, but I didn’t want to sound defensive, so I let it go.
When we got back to town I asked where her home was to drop her off. She gave vague directions, then told me to pull into a convenience store. At the convenience store, she got out and said she’d walk home from there.
I continued to walk by the store she worked in every day, but never saw her there again. Sometime later the store closed. I never saw or heard from her again.”
Oh! That Kind Of Skater!
“This girl who I’d been seeing told me she’d been skating forever, that she was on a national skate team. I’m like, cool cool, tell me more. She talked about her friends skating with her, all good. After no less than seven months of regularly talking, she invites me to a skating performance. I’m asking, what will they perform? She says, ‘The Nutcracker.’ And I go, ‘Oh wow. That’s… interesting. So will you make up for the dancing with a skateboard performance?’. She looks at me in disbelief, bursts out laughing. Obviously, she was an ice skater. Not sure why that never crossed my mind. I totally imagined her to be a sk8er girl, from her personality, that’d have been a fit. Oh well. The nutcracker performance was dope, though!”
Wow This Guy Has No Luck
“Had a girl try to convince me to cut off my long hair for the date. The first date. She knew I had long hair, it wasn’t a blind date. She also brought her dog unannounced, insisted it go into the bar with her, then only talked about money for the next hour or two, constantly pestering me about how much I made. The second I caved the date was over. Ms. Moneybags still let my apparently broke self pay the tab.
One girl started crying when a certain song came on and demanded to be taken home, maybe 20 minutes into the date. I guess it reminded her of her dad that had passed. No hard feelings on that one, obviously. I did my best to cheer her up on the way home. Never heard from her again. Hope she’s doing alright these days.
One girl brought her brother along and they stole my roommate’s paycheck off my living room table.
One girl immediately talked about her baby that died. Like, I showed up in a cab, got a hug, a few seconds of chit-chat, dead baby. It came up several times again while she was pouring spirits faster than I could drink it. She would alternate between telling me how she’s isn’t going to hook up with me, then saying very sensual things and showing me her bum or making me ‘feel how flat her stomach was.’ In her defense, it was indeed quite flat. She all but dragged me to her room and we got to it pretty quickly. Again, several times during this she brought up her dead baby. At one point she’s giving me a very enthusiastic handy while staring straight into my soul, with a terrifying smile. It was really, really, really weird. Towards the end, she was nearly screaming at me to, and these are her words not mine, ‘finish in her.’ I was already really skeeved out with the dead baby thing and the sudden intake of spirits certainty didn’t help, so thankfully I didn’t do that.
Turns out she was actively trying to pregnant as fast as possible. She spent the entire next day (literally all day, my entire 12-hour shift at work, then hours after I got home) of her constantly demanding I get her pregnant and that I was a horrible piece of trash for not wanting kids, on and on and on. It was incredibly bizarre.”
Some Pretty Heavy Stuff
“When I was younger I had a hookup with a girl, halfway through the deed she started sobbing uncontrollably, I stop obviously and ask what’s wrong, she proceeded to tell me how her grandfather had been violating her since she was 7-years-old….. I tell her how sorry I am and how awful that is and that she should go to the police. All the while she’s still sobbing and gently stroking me. Still crying she starts going down on me again I say ‘Hey no look it’s fine you don’t have to do that’ tears running down her face she says ‘but you haven’t gotten off yet’.
Hands down the worst sad cringe moment of my life. We actually stayed in touch for a while and dated for a bit but she wasn’t in a place emotionally to be having a relationship with anyone until she dealt with her trauma. She seems to be doing ok now though.”
The Bartender Had His Back
“Matched with someone on tinder, we chatted a couple of days on and off, we eventually decided to meet at the bar, she spent a lot of time on her phone, seemed extremely eager/anxious, looking at the front door of the bar, people kept walking by us and saying hi to her so this was obviously her watering hole, we got one drink in before whoever she was messaging/eagerly awaiting arrived, she excuses herself for just a second. 10 minutes later she still isn’t back, the bartender comes down to my end, asks if we’re on a date, I told him yeah, he goes ‘That was her coke dealer, your drink is on me if you wanna dip, she ain’t coming back and if she is, you don’t wanna be around her.'”
One Thing Not To Say On A Date
“I was walking past a rickshaw one night with a dude and a lady in it, and the lady says, ‘I always feel bad for these guys, I feel like I’m too heavy.’
And instead of reassuring her, the guy says, ‘Oh don’t even worry about it, these guys could carry a moose!’
I think he knew as soon as it left his mouth that he wasn’t getting anywhere on that date.”
A Rollercoaster Of A Story!
“More like a first date that never wanted to end so this might belong. I had just moved to a different state and decided to try out the online dating scene. This was before the days of Tinder and Match.com was one of the only options. I matched with a guy that seemed to be pretty genuine, decent looking, and wasn’t horrible in phone/text conversation. We decided to meet at a restaurant to grab appetizers and drinks. When we got there, the conversation seemed great.
He even looked like his picture. Shortly after getting there, we both decided to order dinner because we were both hungry and had a rough day at work. He offered to pay. Shortly after ordering, he grabs my hand as it was resting on the table next to my drink. He proceeds to hold it and seems to have no desire to let it go. Sadly, he still seemed very genuine. He then switches our conversation from work and friends to how he has baby fever. (We’re both in our young 20s mind you.) He’s still holding my hand. No amount of tugging will give him the message and at this point I’m beyond creeped out to the point of scared. I don’t believe I said a word to him after he uttered the words baby fever. Food comes. Thank heavens! I can finally get my hand back. Nope. Think again. He wants to hold hands and eat at the same time. Of course, me being a young 20 something, I ordered a salad which is totally doable with only one hand. Rookie mistake.
The waiter comes over and can obviously see my desperation. (I’m fairly certain I’m sweating at this point, my hand feels gross, and I’m awkwardly looking around for an exit strategy. I can’t even grab my drink without making a bigger effort.) Then the glorious moment happens. The waiter accidentally spills my vino on my date. My hand is finally free! My date rushes off to the bathroom to clean up. He seems overly understanding after having an entire glass of red dumped on him. The waiter apologizes then looks me dead in the eye and says ‘I got you, go now. I’ll take care of it.’ I immediately get up, say thank you, and got out so fast I almost forgot my coat. (Waiter chased me down to give it to me.)
At this point, I have no clue what happened after I left and I didn’t care. I get a text later from my date that says how he hopes everything is ok. Ignore and block.
A day or so later, I get a message from a co-worker that someone is waiting in the hallway for me. (Where I work, you can’t get into the building without being an employee.) I think nothing of it and walk out to see who it is. It’s common to wait there as our office is only open for the IT nerds. I open the door, turn to see who’s there, and yelp. ‘Excited to see me?’ And I’m messed up. I must have had the biggest look of disgust and terror mixed with gas on my face. Mr creepy hand holder online dating sucks the first date works at my company. He asks how my grandma is doing, I play along assuming that the waiter said something about her. He reaches out to grab my hand and I yell out I’m infertile. (I had no clue where that came from nor did I have any idea if I was.) He looks at me strangely without saying a word and I used the awkward distraction to go back into my office.
I get a message from him later that day on my work chat asking if I’d be interested in fertility treatments. I noped right out of that conversation and went directly to security. I never heard or saw him again.”
Long Story Short: No Second Date
“This happened while I was working at a bar.
Had a girl come in alone, 20’s, dressed nicely, nice hair/makeup, etc you could tell she’d gone the extra mile. She ordered and waited for her date at the bar, looking nervous. Then this guy strides in through the door wearing full grey tracksuits, looked like he just got outta bed, and boldly exclaims ‘YOU ALRIGHT LUV?!’ I wish I could describe the look on her face. It was over before it started.
Lucky for me they took a table in front of the bar so I could watch how it all went down. She was already somewhere else, and her bathroom breaks became longer and more frequent. Each drink this dude had took 2 years off his age and increased the ferocity of his hand gestures, by the end of it we had a beautiful, uncomfortable and angry girl with an inebriated child in man’s clothes.
Long story short I don’t think there was a second date.
Perks of working a bar, you see this sorta stuff all the time.”
Just A Genuinely Bizarre Encounter
“I was in Maui for vacation and walked over to eat at a restaurant near my hotel. I sat next to this couple who were just sitting down as well and they had some light small talk and ordered drinks and food and stuff. He pulls out his phone and records a snapchat video of her and saying “This is my friend from Utah” and it all seemed like they were hitting it off, then it got weird. He appeared to lose his ability to strike up any conversation, he kept re-watching the video he just took with his voice shouting the same line over and over and ignoring her at the table with him. She kept trying to talk to him and keep things going, but he just wasn’t responsive or talking and just kept watching his own video with her in it. For like 45 minutes this goes on and then they get up and leave.
I happened to leave within 5 minutes of them and I walk out of the place and I see him hyper-aggressively making out with with her. To the point where I thought his tongue was going to hit her stomach. It was so weird.”
Delusional With Expensive Tastes
“She was really superficial and vapid. Gave a list of what a real man has to have in order to be with her. The list was like have a Mercedes or BMW, wear a Rolex, have a suit, own their own home, have a condo in the city for weekend fun, own a boat, has to have an inheritance, can’t be more than 2 years older than her.
I was peeing myself laughing in her face because she was an 18-year-old freshman in college and believed this was a prerequisite to date her. She’s here eating ramen noodles yet wants daddy to have all this. Like ma, what are you bringing to the table?
We graduated recently and she didn’t date anyone during undergrad because no one was ever enough for her. Those prereqs were weird because she hadn’t grown up in opulence, she grew up in a low-income county of our state.”
Abnormal Response To A Normal Night
“First date back into the dating scene after being out of it for 14 years. It had changed a lot.
So I go out with a girl from one of the apps. Have a great time, we part ways for the night. I get a slew of angry messages about why I didn’t make any moves or invite her over after. Like crazy texts. Nothing about anything physical was discussed prior and the last time I went on a first date was just before I had turned 17. So at 31, I was not in the know about the hookup scene. Her reaction to nothing physical was insane, way over the top.”
Hey Man, Maybe Don’t Play That Movie Next Time
“Oh, I got one. Met a girl on Tinder, chatted for a couple of weeks. She comes over to my house to hang out and watch a movie. We smoke a little bit and decide to find a horror movie neither of us had seen. We chose “Maniac” with Elijah Wood in it. So we get all settled in, turn it on, and the first scene of the movie is Elijah meeting a girl online, her going to his place, and him murdering her. There was no second date…”
“I met a girl on an airplane, got her number. She was doing school, I was interning. We met a few weeks afterward for dinner. We meet at the restaurant, try to go for a hug.. she’s anxious and I can see it on her face, and kinda returned the hug. Weird.
Well, not long after we sit down, she tells me she was assaulted by a member of her dance team, reported him, he was kicked out of school and threatening her life via text (it came out that he assaulted other women, too, so she spoke first)…
Well, she’s freaked all dinner and has her eyes staring at the door, scared he is going to enter any second. The conversation was pretty difficult to get going.. especially cause she was warning me he might actually show up (why did she tell him, I don’t know?)
When she’s ready to go, I led her in an Uber to her dorm. We waited for some of the other guys from the dance team to watch out for her the rest of the night.
To be fair, her first date was probably way worse than mine.”
Okay, Not That This Isn’t Awkward Or Anything But…
“Back when I was single my friend’s wife hooked me up with a woman she worked with. Said she was cute.
She wasn’t. She spent the whole date talking about how she hadn’t had gotten laid for 17 years and she had only had hanky panky with her college boyfriend. There was zero interest on my part so I chose not to pick up on the hints. It was our only date.”
This Girl Was CRAZY
“Met on OKcupid, met up at the boardwalk, and went for a walk on the beach. She spent the entire time talking about how smart her friend is. He’d discovered the secret to making cold fusion work and it could provide free energy for the entire world, apparently. Neat.
But unfortunately, the government stole his research and all he had left were the original notes from a failed attempt. The scientists wouldn’t buy the notes from him and nobody would listen to his ideas anymore.
She’d gone from weird to absolutely crazy by this point. Even if this whole story was somehow true, for the sake of argument, why the heck talk about it on your first date?
Anyway, we met up with some friends of hers and she vanished at some point. I asked one of them what happened and they shrugged.
So I guess she ghosted mid-date because somehow I must have been the weird one? Never did follow up to find out though.”
Get Bent, Brittany!
Oh I got this one!
Matched on Tinder, we seemed to hit it off really well at first and she was cute.
She asked if I wanted to go meet up at a brewery at a certain time. I agreed.
Earlier the day of the date I sent her a quick message saying I’m looking forward to it and confirmed the time to meet. She says she is looking forward to it as well but maybe a little late. I offer to meet up 30 minutes later and she said it would only be a few minutes so we could still aim for the original time.
The time comes around and I get there a few minutes early to stake out a table (a busy night). I text her saying I’m early and where I am but not to rush. She responds with ‘thanks! I am just getting ready to leave my house!’ right when we were supposed to meet mind you. I’m a little ticked then I remembered that she lives in a town THE NEXT COUNTY OVER! I ask her if I can get an ETA and she said ‘google is telling me about 45 minutes.’
Now I’m faced with the dilemma of do I sit here by myself like a goon by myself for 45+ minutes (parking was bad) and wait for her or do I say forget it and leave. Against my better judgment, I decided to stay and bought myself a drink or two, surfed Reddit, and made small talk with the other people there.
50 minutes later, she finally shows up and, while she is still cute, she didn’t look much like her photos. Whatever, let’s give her a shot. She’s talking mostly about herself and not asking much about me, which is annoying, but not in itself a total deal breaker. After chatting for a bit we went to get another drink.
On the way back to our spot from the bar I somehow managed to trip and spill an entire bottle all over my favorite shirt. She gives out a very half-hearted ‘oh no’ before I excuse myself. I go excuse myself to go wash off a little and get another bottle. I told the bartender my story and thankfully he comped me a drink (best part of the night).
When I am walking back she is on her phone and looking concerned. Once the call is over I ask her what’s up and she says ‘my mother just called and said my great aunt had to go to the emergency room and looks like she may die soon. I need to go.’ To this day, I’m still mad at myself for not calling her out on such a by-the-books nonsense cop-out but in the heat of the moment, I was so stunned I couldn’t think of anything and just said bye.
I got back home and realized that I waited 45 minutes at the bar by myself for a date that lasted 20 minutes. The following day she unmatched me on tinder
Honestly, things could have been much worse, but they could have been much better.
From the bottom of my heart, get bent, Brittany.
“My date invited me over to his place and started singing and playing his acoustic guitar. It may sound romantic but he was awful at playing guitar and singing. And he didn’t stop for 30 minutes. For some strange reason I decided to stay (should have left but wanted to give him a chance) and we started fooling around. He was having a hard time finishing, so he stopped like three times and said he has issues with finishing because he believes he beats off too much (super awkward). Needless to say, I never talked to him again.”
She Tried To Summon Some Demons
“Tinder match, she seemed fairly attractive and we hit it off in some conversation. Over a few days, I wanted to meet her as she seemed great and down to earth. Suggest we meet at a park, go for a walk and then something to eat afterward. She gets excited, says she knows just the place, a very old famous bridge just north of the metroplex (Dallas). I was clueless but obliged since the google pics looked like cool history.
Mid-day, show up at the park, waiting around when someone +50lbs heavier comes up to me asking me if I’m Michael. Turns out I got catfished and good. Not to be rude, I go for the walk because the bridge at least looked interesting. We’re walking up to it and she smells like she hasn’t showered in a week, she’s talking about something but that Texas spring heat is amplifying that smell. Get to the bridge, I’m interested in it (built in the 1800s or so) then she mentions it’s history, I’m game. Says it’s an old goat pass and there was a goat herder that took it everyday until some Klan members hung him off of it, but his body disappeared and the bridge/area is haunted.
Okay, cool story I guess, but she’s more excited than ever now that she’s scratched the surface, and man… I didn’t realize the void I was standing on. She starts talking about how ghost hunters aired here one time, it was her favorite show she told me. She finds the location someone on the show got force pushed by a ghost and then reenacted it… I kid you not.
I’ve had it, my patience and kindness are paid in full and I’m gonna get out of there. I mention I’ve got something to go to excuse and she gets bummed until she’s had an idea. ‘Give me a second’ she says. She tries to jog down the trail like 30ft, looks off the path, finds a branch, starts drawing in the pathway murmuring something, throws something out of her purse, and looks around the trail like she’s waiting for something. I’ve officially freaked the heck out. She comes back disappointed, I ask what that was about and she says ‘I tried to summon the demon that haunts the bridge.’
‘Hmmm, interesting, AND WHY THE HECK WOULD YOU DO THAT?!’
I’m heading back for the parking lot with or without her at this point, IDGAF. She’s trying to keep up, mentioning something about a cursed ceramic doll that got nailed to a post without shattering or some nonsense. Get to the car, she’s like ‘Wanna come over?’ Somehow ‘no’ just didn’t seem powerful enough. I peeled out of there and said a prayer. There’s more to it but just doesn’t come across well via text. Coworkers thought I made it up, but I swear to God almighty she put fear in me. One of those times I’m glad I did it for the story but… never again.”
The Meat Guy
“I was with my S/O in an Indian restaurant.
There was a Chinese girl with this Western dude. Not only was their language barrier terrible, but the dude was also not the nicest. When they entered the restaurant, my SO and I instantly knew it was the first date because of how awkward they were with each other.
The guy proceeded to put more meat on the girl’s plate. She kept saying she didn’t want them. He responded by saying that she needs protein to ‘have more muscles because she’s too thin’ for him.
A little bit later, she tried pouring some tea into his cup. He blurted out loud how too much tea is bad for him because they’re unhealthy. He proceeded to explain that he has a daily tea limit.
There were other awkward parts of the conversation. We didn’t really want to eavesdrop, but they were talking loudly on a table beside us. It was also tough to not notice them because the guy was talking really loudly over her all the time.
We now call him the meat guy and will always remember him.”
The Waitress Earned Her Tips That Night
“When I was in high school, this guy in my friend group asked me to tag along on a first date with a girl he liked. To this day, I have no idea why. The girl was also in our friend group, so we knew each other, but I could tell she also wondered what I was doing there.
We met at the mall (because it’s the 90s) and had dinner at a Pizza Hut. He was visibly nervous and quickly knocked over his water cup. Whatever size cup you think would be normal for a restaurant, double it. The thing was huge. Water went everywhere. All he could do was laugh nervously and attempt to mop it up with napkins. The waitress helped mop up the water and brought him another (giant) cup of water. His date took it well, and I think she could tell it was just a simple goof. No harm done, right?
A few minutes later, he knocked over his water again.
His date had a look on her face that said, ‘Oh for Pete’s sake,’ and I couldn’t hold back the laughter. He was beet red. The waitress earned her tips that night.
Despite the rocky start, he seemed to get a little more comfortable as the evening went on, and the rest of the date went well. They dated for several weeks, but it was a high school relationship, so you know.”