First dates can be nerve-raking. You build up this confidence and try to look your best for that wonderful night, but it goes downhill — usually from the start. What do you do then? Continue and be polite, or get out of there as fast as possible?
In this article, people share their weirdest first dates and how they handled it.
[Source can be found at the end of the article]
Met a man from OK cupid. Nothing fancy, just a coffee shop date downtown one evening.
He maintained eye contact the entire time, I swear he didn’t look away for even a second. When I told him it was making me really uncomfortable, he asked “Why do you think that is?” and then proceeded to ask many more way-too-personal questions that I did not have answers to. It felt like he was performing some kind of bizarre social experiment to see how much he could make a socially awkward young woman squirm with his unwavering gaze. There was no second date.
Met on Plenty of Fish. Her profile was ‘looking for women’ which at first I thought was odd because she messaged me first, and my profile is of me, fully bearded and clearly indicates ‘male’ in my description. We met at a bar, and she was very quiet. I really liked her and we had great conversations online. I thought she was just shy. She disappeared halfway through the night. I was really sad because I had just gotten the courage to try dating again after a really intense breakup and I really liked her. She messaged me a few days later after no response explaining that she thought I was a trans male on hormones, not an actual man. I was clearly very upset for multiple and very different reasons for a while after that.
Met a guy at the skate park when I was 14, he asked if I’d go out with him the next day. I thought he was gorgeous, and when he said I should dress up I expected something special.
He took me to his little sister’s funeral.
When I was I was in high school I went out on a date with this girl I had a big crush on. We went to the zoo and then grabbed some food as a diner. Afterwards, we had to split up in order to get our trains that were going in the opposite direction. I awkwardly tried to lean in for a kiss, while she went in to hug me, and I ended up headbutting her in the face and her nose started bleeding. I was embarrassed as fuck, so I just asked, “Are you okay” and when she said, “I think so” I just waved goodbye and walked away into the train station face palming really hard.
I’d been seeing this guy for a couple months but we never actually went on a date. So this being our first date, we went to get some froyo at Tutti Frutti. He comes and picks me up and he brings his mom along. He apparently can’t go on dates unless she comes with him. So we are sitting at our own table, eating and I lean over to show him something on my phone. His mom gets up and marches over to our table and grabs my phone practically shouting “What are you showing my son?!?!?” It was a funny puppy video. I took back my phone broke up with him and walked home.
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Met on tinder when I had just turned 19. We decided to go to a really popular park downtown, and had a rad time, right up until she told me she lied about her age, she was 14 (she looked 20 and said she was 18), and that her parents were working literally 30 feet from the shop we were in. I’ve never run so fast in my life. Got calls and texts for about 3 months after, telling me she loved me. Oh boy, I get anxiety just talking about it.
A month ago I went on a first date with a guy, we hit it off, he was walking me home afterwards, and decided to do one of those romantic moves where the guy dips the girl and then kisses her…only he miscalculated, slamming the back of my head into the sidewalk. I ended up with a moderate traumatic brain injury and he broke his finger trying to stop the fall. We were right outside a hospital when this happened so we ended our date in the ER with all of the staff cracking up at the ridiculous story we had to tell.
I went to the cinema with a school friend. At this point I didn’t even know it was meant to be a date. Afterwards he asked if I wanted to play some games at his place. So I said yes. As soon as I walked into his front room I was met with about 8 of his family members. He had invited over most of his family to meet me. They all believed I was his girlfriend, and that we had just come back from a date together. I felt very uncomfortable, and couldn’t bring myself to tell them that we weren’t actually boyfriend/girlfriend.
He was a lab partner in college, he asked me out, we met for dinner. He locked eyes with me over his salad and told me he thought I was “as beautiful as Hitler’s niece.” I could not look less like her, but okay. He was a little intense and a good deal larger and stronger than I, so I texted a girlfriend to meet me at the bar across the street so I’d have an excuse to run after our date ended. He then described to me how he thought I’d be “exquisite while pregnant” and how he’d searched “so long for a woman so compatible with his genes and heritage,” rolling his sleeve to expose a swastika tattoo. It was then I excused myself to the ladies’ and got out the kitchen into the waiting arms of my best friend. I had to change my number, he was so insistent.
A childhood friend of mine asked me to go to dinner after we ran into each other at a party. I thought this would be great as she had gotten pretty cute since last time I’d seen her and it was all was going well when we were texting. I met her at the restaurant and to my surprise there was a middle aged business looking guy there as well. As soon I sat down both of them tried to recruit me to a one of those pyramid marketing schemes. After I declined and went home I would get texts regularly over the next month asking me what went wrong and why I didn’t want to make all this easy money. I’m pretty sure I didn’t even get to order dinner as well.
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Have been talking to a guy he invites me over mid-day to watch a movie. I say fine, head to his place. I knock and wait at the door to apartment for like 5 minutes, check text message to make sure I have the right place. He invites me in and tells me he needs to finish something on the computer. He proceeded to ignore me for like another 30 minutes while playing League of Legends on the computer it was so awkward. Bonus weird points he shared a bedroom with his sister in a small apartment. I understand I was a broke college student but this guy had a job as a charge nurse at a local hospital he was very socially awkward. Definitely weirdest first date.
Got a call from a friend of a friend who I thought I’d met once before, asking if I wanted to go out tomorrow (Saturday) night. Sure. Went out to her place about 40 mins away. Realized upon arrival that I didn’t actually know her name. Had dinner, talked, made out a bit, talked about going out again, made out some more, called it a night at around 1am. Tried several ways to get her to reveal her name, to no avail. Dropped her off at her place, drove home, went to bed.
Realized the following morning that she had never spoken my name either, not on the phone or in person. Further realized that I didn’t have her phone number. Called mutual friend to ask for her number. Mutual friend had no idea who I was talking about. Gave him address of girl. Said he didn’t know anyone from that town and the address wasn’t familiar.
Never heard from her again.
Went on a date to a sushi bar with this guy, pretty cute, met online. He ordered Ramen for us both because it was the best side to sushi I guess. I am not a chopstick master, I tried using them and kept dropping noodles and making a mess, so I asked for a fork from the waiter. Date starts SCREAMING “You do not use a fork! It is disrespectful! You are supposed to use chopsticks! If you can’t than don’t eat it!” The waiter stared at him, then looked at me “It’s okay if you need a fork.” I had tears in my eyes and just mumbled “No thanks, I’ll be going.” Handed him some cash and left.
Had another where the guy invited me over to watch movies, was moving furniture (so I just stood awkwardly since I was ‘a guest and petite lady’) so once we sat down to watch the movie he smelled to high hell, proceeded to take his shirt off and say “Just wanna show ya what you’re working with.” It was awkward, but I liked the movie we were watching so I stayed, afterward we were talking and he started laughing at something and I noticed his teeth had yellow/brown/black stains. I’m shallow, good teeth are a plus for me. We ended the date and that was that.
Met up with the girl at a coffee shop. The entire ‘date’ she would not stop talking about her ‘androgynous’ gay best friend (her descriptor words, not mine, but having seen about a dozen photos I’m inclined to agree) she was obviously in love with. Literally, not two sentences could go by without her talking about him. I asked politely to change the conversation a few times, didn’t work. After about 20 minutes I told her I had to get going but she asked if I would walk her home since it had gotten dark. I’m a gent and a glutton for punishment I agree. She still keeps talking about him. Gave me a kiss on the cheek at her door and I never answered her calls or texts again. She was really really pretty too, oh well.
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Date was dinner and a movie with a girl. We got the movie time wrong so went to dinner first. After ordering she starts looking at her phone a lot and has this weird look on her face. I ask what’s wrong she says her cat has gone missing. She goes outside to make a phone call and comes back 5 mins later saying we have to go. I get our food boxed and pay the bill. I drive her back to her dorm and she runs inside with no good bye. I shrug it off and go eat my boxed cold dinner. Later that night I check Facebook and see her on a date with another guy. I send her a message asking how her cat is.
First date to a movie (The Hobbit) with a girl I started talking to on Facebook. I get to the cinema and find out that she brought both her parents to our first date.
Okay, maybe she just wanted me to meet them. A little early but alri- Nope. They’re watching the movie with us.
We get movie snacks and go into the theatre. I take a seat next to her and then the parents each take a seat on either side of us, with my date and I in the middle. I was sitting next to her father. It was super uncomfortable, so I said that I “liked sitting next to the wall better.”
Barely anything happened between my date and I. We shared a straw for the soda and that was about it.
So I had met this girl my second year of college. She was pretty cute, and my roommate had a thing for her friend, who was also cute. Long story short, dark apartment, 4 people, wandering hands, etc. And then the two girls left. But that’s not what this story is about. This story comes a few nights later.
Since we both lived in campus, (me in the apartments, her in the dorms), dates were kind of tough. But she came over, we drank a little, and I go to walk her back to her dorm. We are walking through the practice football field, and she THROWS HER PHONE AND BAG IN OPPOSITE DIRECTIONS, and takes off into the night. Thinking she’s just messing around, I go to grab her bag, but can’t find her phone. I now, can’t find her. So about an hour later, I go to her dorm room and get her roommate. The night culminates in 3 cars driving around the area screaming her name, police cars cruising the area, and me and the roommate’s boyfriend on foot. She was found at a house party at her cousin’s house, which was apparently nearby. She was brought back to her dorm room, where she asked if she could borrow my phone to call her therapist.
I never distanced myself from anyone faster in my entire life.
Asked out one lady, went to pick her up, she didn’t want to go to dinner, wouldn’t see any movie over PG. We drove around and all of my questions were answered with yes/no and no follow up conversation. Offered to do a half dozen other things, no. Asked if she would like to go to a little restaurant that had live music in the evening. Wouldn’t go there because they sold beer/wine. Took her home and that was that.
Set up on one date. Offered her dinner, no, she wanted to go to a bar. Every five minutes she saw someone she knew and would leave me to go talk to them. Spent maybe ten minutes of that in the two hours we were together. Friend of mine showed up and sat at the table next to me. Date showed up again, we talked for two minutes, again saw someone she knew and went to talk to them. I got my coat on and said good night to my friend. He asked about my date and I told him one of her many friends could take her home. I went out the door.
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Went out with a guy who was a few years younger than me. At the time, I was late 20s and he was early 20s, so I didn’t think much of it.
We went to dinner first. After dinner, he wasn’t ready for the date to be over yet, so we went driving around. I was driving, but I got the feeling he was steering me someplace specific (hey let’s go left here, I don’t know what’s down this way!) Didn’t get a creepy vibe from him at all, and I was the one driving anyway, so I just went with it.
Eventually we ended up near a shopping mall. “Hey let’s go in, just for fun, I haven’t been to the mall in ages!” K, sure, why not.
This is where this began to be the weirdest date of my life. For the next 90 minutes or so, he kept acting like he was walking aimlessly, but then would make a beeline for specific stores. Each time I noticed this, he would just happen to have a friend working in that store right now, isn’t that so weird that we’d run into my friend here!
After the 3rd time it happened, I really began to feel like I was going on a tour to be introduced to all his friends in an effort to prove that he knew a girl.
Finally, we left the mall, and he suggested we stop for ice cream to end the evening. There was a Cold Stone Creamery nearby and I suggested it. No, he wanted to head back toward the restaurant where he’d left his car. Okay, reasonable enough.
If you guessed that he wanted to go to a Dairy Queen where two of his buddies worked, you are way better at predicting things than I was.
We are walking around and a guy asks us if we want drinks, that he is holding. I say no, we keep walking and he is clearly following us, we change roads, side of road and walk off into the darkness.
Went to a pier, started making out and she sits on my lap. She tells me she heard a noise behind us, we see nothing, keep making out. No one was there it was a dark quiet pier.
We make out for a while and I close my eyes, after who knows how long I open them and a guy 40 – 50 years old, big build wearing a leather jacket with one hand in the pocket asks if he can join in and tries to kiss my date. I push him away and tell him I’m calling the police, he tries to grab her but she slaps him and I stand in the way.
He is in our path to leave, my phone has 0 battery and I know that. He still has his right hand in his pocket, which to me means strong possibility of a knife. I wasn’t about to die for this and contemplated if I could push him hard enough for him to fall off the pier and make a run for it, but it wasn’t a sure thing and I was terrified.
I take out my 0% battery phone and pretend to dial, and put it to my ear. He starts running away and we stay back. My date starts crying, I hug her and we walk away.
I went on a date with a guy I had met online. He wanted to meet for drinks, so I went to the pub and waited. He showed up 20 minutes late on his bicycle, proceeded to come into the bar and down two pints after giving me a point and a wink. I overheard him tell the waitress to “put it on his tab” and then he came over to the table with another beer. He proceeded to tell me about his two boys (no mention of them in our previous conversation) and how his mom wanted to take them all to Disney World. He told her that would be too expensive, so he left his boys at home and he and his mom went to Disney World instead. Then he proceeded to tell me that he rode his bike everywhere because after his sixth DUI, “those stupid cops” took his license away. He mocked me for drinking water, then in his next breath told me that he could really see falling in love with me. In 20 minutes, I got about ten words out, and most of them were me telling him I had to go.
I later found out that he worked for a friend’s father, and that he was married.
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I was 22 at the time, and I went out with this 32 year old attorney. She’s cool, she’s pretty, but the date was strange.
We’re talking over dinner, and I notice she has a big scar on her arm. Managed to find a polite way to ask about it — turns out she’d been hit by a car while crossing a street and broke her arm.
Anyway, we leave the restaurant after dinner and stop at a coffee shop.
A question I always like asking people is ‘what’s your greatest fear?’ because you can learn a lot about people that way. So I ask.
She gets real quiet and contemplative. Like, she’s REALLY thinking about this one. I’m convinced I’m gonna get a really deep and meaningful answer.
She finally looks up and says: “I think I’d have to say bears.”
Walking back to our cars, I could not get her response out of my head. BEARS!?
Since I couldn’t get that out of my head, I definitely wasn’t thinking about the earlier conversation in the restaurant, and I decide that we should quickly cross the street just as the light changed from ‘green walking man’ to ‘red flashing hand’ and…
We almost get hit by a car. I see the PTSD flash before her eyes, and in that moment, I became acutely aware that I had never messed up a date so badly in my life.
There was no second date.
Took a really pretty girl out on a date. She was 18, I was 22. I’m pretty well known in my small town, so she knew me as a friend of a friend. When I picked her up, the plan was to go to dinner, then back to her brother’s place, who was out of town at the time.
When I picked her up, she barely spoke to me. I take her to dinner, she orders the most expensive thing on the menu. We go to her brothers, I initiate making out for all of 5 minutes, and she uncomfortably asks me to take her home. Never spoke to me again.
Now, why was this weird? My friend, knowing I wasn’t prepared to take a hot girl out, gave me Adderall to take beforehand. I’d never taken it, but he assured me it would make me feel more confident. I popped three of the immediate release pills with a red bull 20 minutes before I picked her up.
I didn’t know why she never called me, but our mutual friend basically said the date went like this, in her words: “He picked me up, and did not let me get a word in. At all. He then takes me to an expensive restaurant, and doesn’t order anything but water, which makes me think he is broke but trying to impress me (not true, just wasn’t hungry…at all). We then go to my brother’s house, he picks a horror movie which I had already told him I didn’t like, and before the previews are over, he was kissing me with a mouth drier than desert sand.
Met on a dating website and texted nonstop for quite some time. He is a funeral director. I came to his house for dinner and a movie. I pull up to him standing in his garage with a suit on, holding a roll of duct tape. I honestly thought about driving away. He told me that he just got called out and I can either go with him to get the body or wait at his house. Um #2 please! He gives me a quick tour of the house and neglects to mention where the light switches are located. I was in the living room of a split level house and I needed to use the restroom. I go upstairs in the dark, feeling everywhere for a damn switch. Never found one. I go to head back downstairs and the heel of my damn shoe gets caught on the 2nd stair. I heard a snap as intense pain ensues. On my way to falling flat on my butt, I take out a stupid plant he had on the half wall.
So now on this first date, I am laying in his foyer, sobbing, with the worst sprained ankle ever surrounded by dirt from the plant. All I kept thinking was that he was going to come home any minute and find this lady laying there. It took about 15 minutes for the pain to subside and allow me to crawl downstairs to get my phone. When he got home, I told him what happened. Not sure that he truly believed how much pain I was in until I had to have an MRI the following day. We have been together ever since and will be married in a month or so.