Sometimes they can be awkward. Sometimes they can be weird. 1st dates are always a little uncomfortable, these are downright cringe-worthy
When You Say The Absolute WRONG Thing at the Wrong Time
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“We met on OK Cupid, and decided on a place to meet for lunch. She’s overweight, but definitely not obese. Very nice, seemed like just the sweetest person. She talked about her job (nurse) and some random goings-on in her life. All’s well.
We ordered and got our food. She started talking about how she had recently lost a ton of weight with diet and exercise… doing it right. She ordered… I think it was chicken fried steak and mashed potatoes? It was something very heavy. She started eating it very happily; it was clearly an indulgence.
‘Man, I just love food.’
And my reply? Well sir, it was just the best possible reply!
‘Yeah, I can tell!’
Her face dropped. She literally put her fork down on her plate, and pushed her plate back a couple inches. I could tell that she was on the verge of crying.
Now, I didn’t mean it like that. I was commenting nervously, and that’s just what came out of my mouth. I stumbled and said something like ‘I mean… don’t we all!’ But, the date was clearly over. We tried to push through some very awkward conversation until the check arrived. Gave each other a meek little hug at the end, and we both got in our cars and never spoke again.
My face still gets hot when I think of that date.”
Big Spender Expects Big Things, Gets Nothing
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“I went to a guy’s house for pizza and a movie once. We’d been on one date previously after meeting online, and it had gone pretty well. He got pizza from this really awesome place and also brought out a bottle of tequila for margaritas. I made my own so as not to be too drunk, but he insists on shots (ugh). I ended up doing one, but then just watched the movie as he continued to drink. Then he says, ‘okay so the pizza was $30 and the tequila was another $30 – that gets me something, right?’
At that point, I was just like dude, I’m not a prostitute or an arcade ticket counter, I’ll just pay you for half. So rude.”
Pre-Date Dinner Turns Out To Be a Bad Idea For His Bowels
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“In my limited dating experience, it would definitely have to be the time I made the mistake of stopping by a gas station to get what they call a ‘steak and cheese ranchero tornado’ for a snack, since it was an hour+ drive to the date and we weren’t even eating immediately (going to an arcade/bowling alley type place, then food.) This was our third date and things had been off to a somewhat awkward but pretty good start.
So I get there and we have all sorts of fun, playing arcade games, glow putt, do some bowling. We decided to go elsewhere to grab some food, since the food there was pretty mediocre. This was when I started feeling the coming storm, as my stomach loudly protested.
We sat down, and at this time my stomach’s protests had turned into cramping and an impending pressure in my bowels. I excused myself to the restroom, and proceeded to spend probably 15 to 20 minutes in toilet-shaking terror.
When I returned, she looked worried and asked if everything was alright. I told her the entire story, gas station snack, the runs, and all.
She still teases me about it.”
Don’t Associate Anything With Periods On A Date
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“So, he picks me up and takes me to King Taco — a delicious fast food place, but probably not the best place for a first date.
He (nicely) offers to pay, and asks what sauce I want on my taco, red or green. I tell him red. Instead of accepting my choice, he decides he needs to know WHY I want red sauce. So I tell him, I prefer red, then he asks why AGAIN.
This conversation continues for almost a minute before he goes, ‘I know why you prefer red!’
By this point I’m annoyed, but curious, ‘okay why?’
‘Because you’re a girl, and you get your period, and your period is red.’
I was horrified. How did he even come to that conclusion? Why are we talking about periods? I just want my carne asada tacos.
I made him take me home after, and didn’t return his calls. We were 19/20 at the time.”
A Guy Sends So Red Flags It’s Ridiculous
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“OkCupid. First date was at a local park with a lake for some fishing. He told me the wrong dock which I went to and waited around for 20 minutes as we texted back and forth trying to navigate to each other ‘I think I see you!’ ‘Oops! That lady was not you!’ When we figured it out, he teased me for being late in a way that made me think he actually thought it was my fault, which rubbed me the wrong way. Then the second or third sentence he said to me was mentioning that even though he is a gun nut, he was not carrying with him that day (WTF? Not a question that ever crossed my mind before). It was super weird and I should have left then, but of course I didn’t want to be rude. My mistake.
He had two fishing poles with him, did not offer me one and instead just used both himself while he talked at me. We barely got past introductions (seriously not even 5 minutes had passed) when an older guy approached us and started chatting him up about living in our state and guns, and ‘Merica. I stood there awkwardly while they talked for 45 minutes. The sun was setting and they were still talking. Just when I was about to leave, these 3 ducks flew up to us and landed at our feet. Two males were aggressively chasing a female to mate. They were so focused on duck-attacking the female that they ran around our legs. My date and the guy were laughing, yelling ‘get her!’ and I was so uncomfortable. They then turned the conversation to firearm laws and my date said to the guy, ‘Yeah, I’m armed right now. You wouldn’t even know it. SHE didn’t know it!’ pointing to me. I stared at him alarmed. ‘I only thought you weren’t armed because you brought it up and told me that you weren’t armed.’ He pulled me aside and said, ‘I only want him thinking I am. What if this guy was trying to mess with you?’
I took that as my final florescent, flaming red flag and dismissed myself.”
People Who Talk On Their Phones At Movies Is A Good Sign They Have Tons More Wrong With Them
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“My first ever date. At the time I was buzzing because, well, it was my first date but looking back it was a cringe fest. Here’s some of the high(low?)lights:
She turned up almost 45 minutes late on what was a really cold night, me just sitting on a bench on my own.
I used to wear this 3/4 length leather jacket, and wore it to the date. When she did turn up, she said ‘I told you not to wear that.’ I remember no such thing.
We finally get to the cinema, and in some bizarre effort to appear quirky and random I ate my ticket after we went through (this was when Jackass was still cool). She looked at me like ‘WTF.’
Her phone went off (not on silent) in the middle of the movie (US remake of The Ring by the way). She then proceeded to answer and talk at normal volume while remaining sat exactly where she was, as people around us SSSHHH’d us relentlessly.
Later in the movie, she tried to kiss me. Right before the bit where Sadako/Samora climbs out of the TV, and I REALLY wanted to see that bit so I didn’t reciprocate.
After the movie she had to get some cash from a supermarket ATM. I bought a small pack of sweets and she was like ‘Are you five?’ Girl, I had turned five at least three times.
On the way out of the supermarket I saw two rather large women wearing clothes that would have been tight on girls half their size. To lighten the weird mood I said something along the lines of ‘Wow, check out those two,’ which she instead took as me ‘checking them out.’
We then proceeded to a bar where we had what was quite possibly the most awkward, stilted conversation I’ve ever had. I’ve probably had more conversational chemistry with a stranger on a bus.
We didn’t have a second date. My bro went on a date with her after I did. He didn’t have much more luck.”
A Kid Is Honest About What He Finds In His Mom’s Room
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“In high school, my freshman year, my parents put me in Catholic school instead of the high school that most of my friends were fed into. So for the first few weeks I sat with random people. Eventually I started hanging around this kid. He had a Nintendo and I did too so we would sit together and play Nintendo. I had no idea he couldn’t hold a conversation for nothing. About a week before homecoming he asks me to be his date, I said heck yeah.
It’s comes to the night of the date, I’m wearing a black dress and my long black hair was straightened by my mom. I’m wearing cute black shoes and my buddy holly glasses. He knocked on the door wearing all black and takes me to to the backseat of his grandfathers car. We were 14, it was fine. Silence permeated the air on the way there, and his grandfather eventually asked ‘what the heck do you think you’re going to talk about at the restaurant?’ No answer.
At the restaurant, I asked him how getting ready was. He told me the long and drawn out story about how he went snooping through his mom’s room. He was trying to find money, because he wanted to buy a flower, and found his moms ‘lipstick’ and not thinking he put it in his mouth. It started buzzing, and he thought that was weird.
I had to tell him that he stuck his moms adult toy in his mouth.
Needless to say, this stuck with me.”
An Awkward Date Turns Into Planning For Another One…With A Different Person
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“I met a really handsome, clean cut guy online – and we met up for a date.
One of the nicest guys I had met on a blind date. He showed up t shirt, jeans, and flip flops.
As soon as he got out of his car (which was immaculate by the way) – he sashayed over to me.
I noticed he was a tad feminine but I figured I was being stereotypical, rude and not open minded.
I don’t remember if we went to dinner but I do remember that the entire night he didn’t want to touch me or anything like that, which by this point was fine with me because he felt so much like a friend. There was absolutely no sexual chemistry or attraction between us.
He then made it a point to tell me his ‘male’ friend was visiting from New York and he wanted to plan a special dinner for him.
We went to the liquor store and he had me help him pick out some wine for the dinner with his friend – the entire time he kept gushing about his male friend who was going to come visit, about how awesome he was and how he was so excited to see him.
The friend sounded like a pretty nice guy. I helped him pick out some wine and we talked about the dinner and what he should cook for him, etc.
I finally asked him flat out, are you gay? And he said ‘oh god no!'”
Chess Nerd Called About By Another Couple
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“Date to TGI Friday’s with my first boyfriend. He spent the whole hour and a half we were there trying to teach me how to play chess and then getting seriously annoyed with me when I wanted to eat or just talk about ANYTHING OTHER THAN CHESS.
What made it worse was the fact that the woman over at the table next to ours muttered ‘at least we’re not on an awkward first date like they are’ to the guy she was with. The kicker is that we’d been together for two years at that point. Spoilers: it didn’t last.”
Wow, That Was “Not Subtle At All”
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“I had recently gone through a bad break-up and a good friend of mine set me up with one of his close friends. I had met the guy a few times before and thought he was pretty chill.
He picked me up for dinner, was very nice and I was looking forward to the night. At dinner though, he ordered for me… His reasoning was, ‘I love this place and know you’ll love what I got you.’ OK, looked past that but whenever the waitress would come over and asked me anything, he would answer. I asked him why he kept answering for me, and he stated that it was ‘his job.’ At this point I am ready for dinner to be over. The bill came and I said I wouldn’t mind paying my half but he insisted. While getting his card out of his wallet, a condom fell out. We both kind of just looked at it for a second. Nothing is really too weird about that, he practices safe sex, cool. But he had to say something and of course it made me cringe/vomit, ‘I’m ready to use this tonight, you?’ Annoyed and over it, I said, ‘Pass.’
We didn’t talk the whole way back to my house but before I got out of his car he told me, ‘Next time, tell a guy you’re not interested before he has to pay for your meal.’ Then he sped off. He was a little more of a jerk, than cringe. But to this day I cringe when I think about that date.”
Pro Tip: Never Go On A First Date When His Mom is Involved
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“Once met a guy on Bumble and we bonded over a discussion for the love of beer and board games, so we naturally decided to meet up at a brewery to play games for the first date.
He met up with me, we laughed, played games and enjoyed happy hour deals. We both agreed that we were having a good time and decided to move to another bar for some more happy hour deals. Note: The only oddities at this point had been him calling attention to a hole in his pants that he had found.. he had been helping his father earlier that day and these may have been ‘work’ clothes. Might I add that the hole he described was in his crotch region. I smiled and shrugged it off.
We arrive at the next bar and he goes to the restroom as we sit down. I order a drink and wait for him to return.
As he sits down he asks me ‘how adventurous are you?’
I respond with ‘depends on what we are talking about.’
‘Well, my mother just messaged me asking me if I’d like to go to see a movie with her. Would you be interested in keeping the date going?’
I thought for a moment and said screw it. ‘Sure, what kind of movie?’
He says ‘She wants to see Fences.’
Fast forward through the research to find a lighter movie, but decide to go see fences.
We showed up and we’re going to meet her in the lobby. I love popcorn and a drink so I went to the concessions to order what I’d like and come to find out his mother is in front of me buying the tickets for us.
We settle into the theater and she sits in a row on the end and he chose the row directly behind her.
As the movie progressed he would ask me inappropriate questions, not sure if it was just because I was embarrassed or what but I was flushed red because I couldn’t tell if anyone else may have heard him, including HIS mother!
Then later proceeds to grab my hand and try and make me feel the hole in his pants.. yes directly near his crotch. I slapped his hand off of mine after he wouldn’t let go and I fought his grip.
Well.. lesson learned.. never go on a first date and say yes to a movie with mom. HUGE RED FLAG!”
Quiet Girl Has a Total Breakdown On A First Date
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“I pick her up to get Eddie Rocket’s. Met her on tinder.
She’s extremely nervous in the car, wouldn’t even look at me. She quietly answers my questions with one-word answers.
I ask her if she’s alright and does she want me to drop her home, I had thought she just really didn’t like me and was regretting everything.
She immediately bursts into hysterical tears. We’re both just sitting in the car in the car park, only met her 5 minutes, and she’s just crying and crying. I had no clue what to do.
She was saying ‘I knew you wouldn’t like me… just drop me home then if that’s what you want.’ And I mean hysterically crying.
She didn’t seem to be able to hear me for a while but eventually she heard me say, for the fiftieth time, ‘I do like you I just wasn’t sure if you were regretting the date.’ I kid you not, she stops crying, turns to me smiling and says ‘Really?’
At this stage, I was very freaked out but was young and dumb so had no clue how to deal with the situation (not that I know now lol). I say yes in the hopes that she’s all finished crying. She’s then all smiley and we go into Eddie Rocket’s.
Back to one-word answers and avoiding any eye contact while we’re eating. I eat as quickly as possible, pay for the food and drop her home to my relief. By the time I get home I had 3 missed calls and 7 texts from her.
I felt really bad because she obviously had some serious issues but there was no way I was meeting her again and just texted her that I wasn’t interested. She proceeded to leave me voice messages for the next 3 days eventually leaving me alone.
Needless to say, it was a while before I went on another tinder date.”
Alls Well That Ends Well, No Matter How Smelly
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“Went on a date to Six Flags, and after the third ride I projectile vomited my breakfast all over his back and arm. We were several minutes away from the nearest bathroom. He wouldn’t let me buy him a new shirt so he smelled like puke all day.
We’ve been married almost a year now.”
Gross Guy Scares A Girl Off Dating For Years
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“During high school, I went on one date with this guy. ONE. He took me to a cemetery because I was a goth and he thought it would get me in the mood. I was weirded out but tried to stick it out. It was one of my first times going out. We sat on the hood of his car and listened to music. Then he tried to kiss me and touch me. I told him to screw off. This was the FIRST DATE. He backed off, then tried it again a few minutes later. I yelled at him again and got off the car. He yelled back, saying he only took me out to make out with me. I was astonished and so angry. He got in the car and drove off. Leaving me alone, in a cemetery, and it was getting dark. I had to walk all the way back into town and use a pay phone to call a friend to come get me.
I didn’t date again for years.”
This Guy Thinks He’s Channing Tatum. And Loses His Mind Over It!
“We were discussing celebrities and he kept trying to hint that he looked like Channing Tatum. He did not look at all like Channing. I try to ignore it, but he cuts me off to list instances where he was mistaken in public. I say that I don’t see a resemblance, and try to again change the subject. Then he starts pulling up Google Images, reenacting poses. I ignore it.
This sets him off. He starts showing profiles of women he claimed to have dated. Claims he could ‘never date a ten’ implying he’s doing me a favor, like he’s so much hotter. Getting sick of his nonsense, I reply ‘neither would I.’ This was my first encounter with a narcissist. He lost his mind. ‘HOW AM I NOT A TEN!?’ He started screaming and freaking out. It started to scare me. He began badgering me ‘IF I’M NOT A TEN, WHAT AM I!? I’M PERFECT, I LOOK JUST LIKE CHANNING TATUM!’
He was losing his mind, pulling up photos from when he ‘modeled’ and trying to continue his comparison with Channing. I found a way to get out of the situation and started ghosting him. When I rejected his text advances, he’d send me these crazy rants how he was doing me a favor since he’s a ten and taking one for the team.”
First Date Goes All Wrong, It’s All Uphill From There
“Met some girl on the internet after talking a little while we discovered we didn’t live too far away from each other and arranged to meet up for a few drinks. A few days before we were due to meet up she texts me saying her friend wants to come too because you can never be too careful with meeting people on the internet. I say yeah that’s fine I’ll bring a friend too then.
So we meet and she spent the entire time talking to her friend, tried my best to make conversation but was getting one word answers back (I’ll be the first one to admit I suffer from social anxiety so I’m not saying it was all her fault but she wasn’t making it very easy either) it was the most awkward 2 hours of my life. My friend ended up coming up with some lame excuse why we had to leave.
About 6 months later she started texting me again and asks me if I wanna go to dinner, I said why not as long as its just you and me. We hit it off big time ended up being together 8 years.”