20 Types of Worst First Dates We’ve All Suffered Through
Dating is rough. If you’ve ever walked by a table of chicas at brunch, then you know that they’re probably talking about their latest adventures in love and life. I know that’s certainly what I always did, regaling my friends daily with what’s happening in my love life, the good and the bad. Mostly the bad, of course, because that’s what makes for the really good stories.
And for anyone who HAS a love life, then you know that the number one evil of dating is the first date. Sometimes, it can be good. Pleasant, even. But most of the time, first dates make us cringe. They’re awkward and weird and you walk away not quite being sure where you stand. Sometimes, even, they’re so bad that they go down in your memory as the worst first date of all time. We’ve all been there, amirite? That’s where these stories come in. Told from real women (who wished to remain anonymous for, ahem, obvious reasons), these are the 20 types of worst fist dates that we have ALL been through. Trust me, you’ll probably recognize your own or your friend’s stories in at least some of these.
1. The date who pursues you, then insists on splitting the check… Like WHAT?Photo: @kumascornerwestloop/Instagram
“I literally had this guy hassle me to go on a date with him and, because I was a dumb college student, eventually I was like ‘Ok, maybe I should be flattered,’ so I went. We get to the end and he TELLS me we are going to split.
Oh, and the best part: Before we go on our date, he asks, ‘Oh, do you want me to pick you up?’ I was dumb but also paranoid, so I said, ‘No, I’ll meet you.’ So at the end of our date, AFTER he makes me pay, he’s like, ‘Do you mind giving me a ride? I walked here.'”
2. The date who meets you with his bros, then is clueless about how to treat women.Photo: maximilianludwig2/Instagram
“I went on a first date with a guy. We were supposed to meet at this bar but I called him and he said he was across the street with his friends from work. I got there and LITERALLY there were like eight finance bros chillin and throwing back shots. They were also being super rude to the bartender and were all giving me the once-over. I slipped out to go to the bathroom and plan my escape by frantically texting my friends for help. I got out of the bathroom and my ‘date’ was there. He apologized for his buddies and said we can go somewhere else.
He took me to this hole-in-the-wall Mexican place where he proceeded to tell me that I was funny ‘for a girl’ and when I asked if he worked with any women he said, ‘Oh yeah, but we put them in the back of the office cause they are too distracting.’ Naturally I tried to high-tail it out of there. He ended up trying to kiss me sloppily and it was super awkward. He proceeded to call and text me for the next two weeks before getting the hint.”
3. The date who literally lives in a bar.Photo: ahautulum/Instagram
“I knew the date was going to go south when he immediately confessed that he lived on the couch in the back of the bar where we met. But he was the drummer in this pretty well known band I liked, and I was 24 and kinda starstruck. He started the date by ordering two pickle backs, we did them, ordered two more and I was like, ‘I’m good,’ so he did both.
Over the next hour, he basically took a bottle of bourbon to the face, spent the whole time talking about himself, then, fairly drunk, told me he’d just quit the band that was the primary reason I went out with him in the first place. He then, of course, tried to get me to come back to ‘his place’, which as I mentioned, was a couch in the back of the bar. I declined.”
4. The date who couldn’t handle a successful woman.Photo: melissaelisebookstyle/Instagram
“A guy told me completely seriously that he was glad I was a writer because he could never date a woman who was in a ‘man’s industry,’ like law or medicine.”
5. The date who tried to serenade in THE most awkward way.Photo: nicoleconnerphotography/Instagram
“A guy took me out to dinner, which was fine, but then on the car ride back home he serenaded PSY’s ‘Gentleman’ to me. He made an extra loop just so he could finish singing the song because we got to my place before it was over. It was so awkward, though I still listen to that song occasionally because it cracks me up to remember that.”
6. The date who insisted on watching a movie in the most creepy way possible.Photo: mr_bobgray/Instagram
“I went out with this guy for drinks. He kept trying to get me to come over to his apartment to ‘watch a movie.’ And then after I said I don’t watch horror films, he responded by saying he would protect me.
The worst part came at the end of the date as I was walking away, he grabbed my shoulders to do a quick massage and told me that was what I was missing out on by going home. It should also be noted that he was an hour late because he ‘lost his keys.'”
7. The date who shows up drunk… and it only gets worse form there.Photo: alexmottern/Instagram
“This one guy showed up drunk on the first date. I didn’t realize it right away because it was my first time meeting him in person (online dating, folks). As I was parking, he nearly hit my car, then got out, came to the driver’s side of my car and proceeded to touch my hair. ‘You’re so pretty,’ he kept saying.
Inside the restaurant, he accused me of being married because I didn’t give him my number right away. Then, he showed me a tattoo on his chest of his ex-girlfriend’s name and told me how he’d been arrested for allegedly choking her. He talked about how he was going to the renaissance festival and how I should go with him because ‘when you’re in a relationship, you do things you don’t want to do.’
I texted a friend for help to tell me she had an emergency so that I could bail. She waited 30 minutes and her text only said ‘Emergency,’ so I was stuck with making something up to leave. When I got home, he had messaged me on my profile, asking if we were going steady.”
8. The date who tries to impress with his gym routine when he doesn’t exactly look like Rodrigo Santoro.Photo: elias_frutos_do_mar/Instagram
“In college, this guy and I were casually flirting while we were both on the board for a club. He asks me out, he’s cute-ish, I say yes. He takes me to Applebee’s… where he orders a half salad… So we’re talking. Turns out we have very little in common.
Then, I think in an effort to impress me, he starts talking about his workout routine… Now, this guy is not what one would call muscular. I wouldn’t go as far as scrawny, but you definitely don’t look at him and think, ‘Gee, this guy works out.’ Which is fine, but then don’t spend 30 minutes talking about the gym.
I’m sure he could tell I was losing interest. So he pulls out this line, ‘I like my face.’ No joke. I think, ‘Cool, guy. Good for you.’ We head back to campus and we go to the club there, where his friend is. We dance for a little, he kisses me and then we leave. It was so odd. And awkward. And cringey. I still occasionally use his line though. I like my face.”
9. The date who leaves you alone and simply can’t give you the proper time or attention.Photo: yoanaalarcon/Instagram
“I had a guy take me to the restaurant where he worked, where he proceeded to get up on stage and sing for the crowd. He left me at our table alone for about an hour. Then he used his discount for the meal. And this was all after I had to sit and watch football at his place for about 45 minutes before we could leave because his team was on.”
10. The date who was very, very cheap.Photo: meg.looyk/Instagram
“I went on a date and the guy took out a coupon and proceeeded to tell me what I could order. The man was very successful, just cheap. I told him I’d order what I liked and pay for it myself. Needless to say, it was the first and last date.”
11. The date who gets lost on the way.Photo: deejo_knives/Instagram
“This date was overseas, where I went on this date with a local and public transportation is the norm so we take it to go to this ‘cool spot’ out of town. I’ve been living in his hometown for some weeks now so I was getting familiarized with the area. As we arrive to the stop, we get off and realize we are in the middle of nowhere except surrounded by apartment buildings and a supermarket. He proceeds to tell me that ‘we are lost.’ We had spent more than an hour trying to see this ‘cool place’ that didn’t seem to exist. I ended up having to take us back to the city and then I find out he ‘forgot to take his ADHD medication.’ I was floored!”
12. The date who almost threw up. ALMOST.Photo: trophywifebarbie/Instagram
“My current partner and I met on Twitter before meeting in real life. When we finally did, we were both bundles of nerves — specifically her. She was so nervous that she almost got sick. I felt bad! Thankfully, she recovered… and after a few years of long distance friendship and a year of long distance love, we’re still here.”
13. The date who is a hoarder… AND can’t stop drinking.Photo: allianceenviro/Instagram
“I went over to a guys house who he lived with his mom. Okay, not a big deal, we were in our early 20s. Then he invited me into his room, and it was straight out of an episode of Hoarders. There was paper trash, bottles, dishes, and junk just EVERYWHERE. I suggested we go out and get something to eat. We walked to this local pizza place, then he took me to a liquor store, bought a 12 pack of beer (I don’t drink beer) and he proceeded to drink it all on our way back to his house.”
14. The date who has money problems, and many other problems.Photo: okpako.k/Instagram
“I had a horrible date with this guy who I met at a Mediterranean restaurant. We went there because he knows an employee at this place, so we get the food for free (to-go). I really don’t care if a guy drops a lot of money on me, but we spent at least an extra 20 minutes trying to order because his card wasn’t working. Apparently, he had money stolen from his account.
At first, I understood until we get our food after waiting for his situation to be resolved. Then, I get into my car. He gets on his motorcycle so I can follow him to our next location. The motorcycle does not turn on. I wait an extra 5-10 minutes for it to function. It eventually does. We get to our final destination and it’s at this Marina. Everything is fine until we arrive to the sailboat where we were going to have our dinner.
So, if you can picture this, we have to make a small leap onto the boat and I’m hesitant to get on because of the jump. He gives me his helmet and I was going to toss it onto the boat. I didn’t know this, but the keys to the motorcycle and entrance to the marina were IN THE HELMET so… They fell into the ocean. They weren’t even his. I ended up seeing him in his boxers on the first date because he was contemplating to swim to the bottom of the ocean to grab them cause his friend was pissed since the keys cost $200.”
15. The date who left her keys in the worst place possible.Photo: globerocketstore/Instagram
“I had a blind date, which went okay. But towards the end, we left the restaurant where we ate and she realized that she left her keys in the restaurant, which was now closed. We walked back in freezing February weather to see if anyone was there, but nope.
She had no way home AND her car was parked in a tow-away zone. I ended up calling AAA to tow it to a place she could park overnight. Then I had no choice but to invite her to my place, where I slept on the couch and gave her my bedroom. She was nice, but I never heard from her again. She probably just wanted to forget that the whole thing had happened.”
16. The date who is a bit TOO enthusiastic about the food.Photo: thecookierookie/Instagram
“I went on a first date with a guy who stuffed tortilla chips into his mouth with both hands. I ran home and immediately told my sister about it, and we still laugh about it to this day. We’ve since called him ‘the two-handed chip eater.'”
17. The date who drags you to the last thing you want to do.Photo: nascarsupdates/Instagram
“I was once dragged to a NASCAR event. I feel like that needs no more explanation, haha!”
18. The date who maybe wasn’t prepared for you to be emotional.Photo: penetralia.x/Instagram
“I met a guy online. We’re at a restaurant, and he goes to the bathroom, so I check my phone, and see that my dad has called me a whole bunch of times, at night and uncharacteristically, so I call back. As the cute, nice guy comes back from the bathroom, my dad answers and tells me my grandma died unexpectedly. I fell off the chair I was sitting on (yep, really!) and started crying. I manage to choke out what happened, so he just asks what to do.
At a loss, I call my friend, who is only a friend but happens to be guy, and he gives nice guy instructions to drive me home along with an lecture about not taking advantage of me. My date kept me comfortable until my friend showed up, and everything worked out fine, but alas, nice guy did not call me again.”
19. The date who was late, terrible, AND made you pay.Photo: another_loststar/Instagram
“I went on a date with a research scientist. He was 45 minutes late and showed up stinking. He apologized for his tardiness (and looked NOTHING like his profile pic, by the way). Then he told me, ‘Sorry I’m late. The experiment I was working on went badly and I had to euthanize the monkey.’ Oh, and he forgot his wallet so I had to pay.”
20. The date that starts off really badly… but has a happy ending.Photo: ecailles_mucus/Instagram
“He took me fishing. I hate fishing. When we passed a gas station on our way out of town, he told me to duck down because his ex-wife owned it and he didn’t want her to see me and call his CURRENT WIFE and tell on him. Two years later… I married him. We’re still together. We never go fishing.”
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