First dates can be awkward. You have to meander through the ever-changing, unspoken dating rules, and find things to talk about other than the basic, “where’d you go to school?” Sometimes, they go well until one small or huge thing happen that utterly changes the prospect of a next date. Read some of the most face-palm, cringiest, and just straight up bad first date moments!
1. Bad Math
I offered to pay for the bill. She insisted to pay half. I didn’t fight it, but I only had a large bill so I did some mental math, pocketed her money and put my bill in. Anyway, long story short, I did the math wrong and ended up stealing 20 bucks from her. She sarcastically said, “thank you,” and I thought she was being sincere. I’m an idiot.
2. Too Kinky Too Soon
On two separate occasions, the first time I’ve gone home to a guy’s place, I’ve seen a horrific sight. Both times, he’s had a variety of intimate toys laid out on the bed. And I’m not talking about regular stuff, either. I’m talking full-on specialist stuff. There were more than ten implements, bundles of rope, and fine leather goods.
Everything was just laid out there, as if he’s expecting me to be like a kid in a toy store with all the possibilities the night has opened up. I mean, I don’t mind getting wild, and if I’m going home with you it’s a pretty safe bet that you’re getting some. But for God’s sake, man, you can’t just put that stuff out there as-is. You’ve got to give a girl some warning. You can’t just assume.
3. Let’s Get You Into Some Wet Clothes
It was our third date and I’d driven my project car because I’d just gotten it on the road. It started raining right before dinner. By the time we came out of the restaurant, it was a pretty torrential downpour. We hopped in the car and started driving to the bowling alley. Well, apparently the seal around the T-tops leaked and a bunch of water had pooled in the frame underneath.
The first corner we went around, it all dumped out on her. She was soaked. Whoops. She said it was alright, but I knew it wasn’t.
4. Sweet Disaster
We order a small snack for our coffee and as it’s arriving at the table, he pulls out his Nokia phone. Trying to make a lighthearted joke, I say, “MAN, that has got to be the oldest phone I’ve seen in a while.” I really dug it in, trying to break that awkward first date wall. Well, it turns out that it was not a Nokia, it was something much more embarrassing. It was his insulin pump.
5. Better Late Than Never?
A while after my parents split, my mom joined a dating site. She met up halfway with a guy who lived pretty far away (at least two hours) and he was late. 45 minutes later, he stumbles into the restaurant completely hammered. He starts towards my mom’s table, trips, and smacks his head on the corner of the table she was sitting at.
He then fell unconscious and began bleeding profusely from the forehead. Literally everyone in the restaurant is frozen and in awe staring at him, passed out, bloody, and drunk. For whatever RIDICULOUS reason, instead of just calling an ambulance and leaving, my mom decides to drive the unconscious man to the hospital and spends all night there to talk to him when he wakes up.
She stayed essentially just to say there won’t be a second date and officially reject him in person. I can’t remember if she drove him home or not but it’s a possibility. She’s insane.
6. Nailed It
I still have nightmares about this date. When I was about 20 or so, I got a date with a girl who I really liked, she was exactly my type and I couldn’t believe my luck. We met in a local pub for a few drinks and things were great. I was getting all the good signs with lots of hand touching and the like. An hour of pure bliss went by and I needed to pee.
After washing my hands, I went to the hand dryer only to find that it didn’t work. I wanted to dry my hands because I wanted more of the hand-holdy stuff. In the single most stupid idea of my life, I thought, “I can fix this!” and put my hand inside the nozzle of the dryer. WHY!? WHY THE HECK!? Obviously, I got buzzed by the electric heating element, fell back, and cracked my head on the wall.
I didn’t get knocked out but I needed a few minutes to sort myself out before going back. I didn’t have the guts to tell her what had happened; dumb idea number two. I had a banging headache and I wasn’t quite right. Not much later she made her excuses and left and turned me down when I asked her for a second date. A year or so later I found out she had told her friend that she really liked me, but I went to the toilet and came out acting really weird and she “wasn’t up for dating someone on drugs.”
7. The Grand, Bad Slam
We were sitting on my couch watching a movie and she moves closer and closer until she is on my lap. As a joke, I started to tickle her and then she started to tickle me back and then it turns into play wrestling. Right before things switch from play wrestling to making out, it took a very dark turn. We both slip off of the couch and she slams her head into the hardwood floor.
She laughed it off, but it ruined the mood and we went back to watching the movie.
8. No Second Date, Bye
The date had been going great. It was possibly one of the best dates I had ever been to up until the point when he suddenly asks me if I wanted to use my hands on him down there. I awkwardly laugh it off and say that I don’t really know him well enough for that. Then he gets all quiet and seems really angry after this. It ended with me just going, “There will not be a second date, bye.”
9. Two Many Kristens
There is this interesting (and cute) woman at work that I’ve flirted with from time to time. I recently gave her my number and told her to hit me up if she was ever free to go out for some fun. The key thing to note here is that her name is Kristen. Fast forward and I got a text from a female friend (also named Kristen) who asked me if I wanted to check out a concert with her on Saturday.
We hang a lot together so I had no qualms showing up to this concert a bit drunk and in a t-shirt, jeans and a hoodie (not looking clean cut). Out of the blue, I see my crush work-Kristen near the front of the concert. I went over and said hello for a bit then said I needed to grab a drink and meet a friend. I kept texting my friend-Kristen and she was replying that she was near the front.
So once again I head down there. I chat for a bit with work-Kristen and keep looking for my friend. I mentioned to work-Kristen that I kept texting my friend who I couldn’t find. When at that moment work-Kristen says, “Is that why you keep asking me where I’m at?” That’s when it dawned on me that it was NOT my friend who invited me out, it was my crush!
I showed up a little drunk, disorderly, and probably seem per-occupied the whole evening. She seemed ticked off after that and has sort of avoided me since this past weekend. Oh well, c’est la vie.
10. An Old One and Not a Good One
This was in high school. She invited me to her house to have dinner with her family and I didn’t know them very well yet. The conversation turned to names we thought were old-fashioned and ugly-sounding. We all threw out a few like Gertrude, Bertha, and Eugene, and then I said the one thing that ruined everything.
I said, “At least that one’s not as bad as Deborah!” I used my ugly voice and everything. Her mom’s name is Deborah. Her grandmother was also at the table with us.
11. Hesitant Eavesdroppers Almost to the Rescue
He didn’t let me order on a lunch date at a cafe because “girls don’t really eat anything for lunch anyway.” So, I drank water while he ate a family-sized pasta dish with his mouth open while talking constantly about fashion. I actually had fun listening to the two women at the table next of us be horrified about how clueless he was and how bad the date was.
They were clearly trying to figure out the best way to rescue me from him. They didn’t rescue me, but I magically got “a text”and needed to leave.
12. Don’t Mention the Carl
I had been flirting with a girl for a few weeks and finally asked her out to coffee. Things were seemingly going well. Somehow squirrels come up and I mention casually, “my friend Carl likes to shoot squirrels in his backyard. He taught me how to shoot but I was never good enough to hit such a small target running across the lawn.”
Her response was, “Ummm, well it’s getting late.” And that’s how the “Don’t mention Carl” rule got added to the list of things I am not allowed to do on first dates.
13. Welcome to the Love Boat
So, I met this girl off of a dating app, in fact, many dating apps. I managed to match with her on OKC, Tinder, and Bumble. She never responded to any messages. But then one day, I get this really strange message on two of the apps. Each is more or less the same. “Hey! Hi! Insert phone number here.” Hm, well okay, I text her. And that’s when the best worst date of my life begins.
She tells me she is moving away at the end of the week. She wants me to go to her going away party. First date. Going away party. Sure, what the heck. I’ve made it a staple in my life at this point to say yes to crazy stuff. The party starts at 2pm. I can’t make it until 5pm. I tell her this. I show up. I am the only one there so far, three hours late. She is jittering off the walls.
She’s talking a mile a minute moving from room to room searching for some nonexistent thing. That’s when I learn that she has kids. The house has toys strewn about and chalk drawings all over the walls. The kids aren’t there. They’re out of town she explains. The going away party is so she can go live with her kids.
I find this out as she explains to me that Mama is on a bender as a vacation from her children. Guests begin to arrive. A guy comes up to me and asks how I know the host. I tell him we met on OkCupid and I ask him the same question. His face drops. He looks simultaneously uncomfortable and really sad. “We met on OkCupid too.”
I do an emotional backflip in my head. This is amazing. I think this is hilarious. I start asking everybody. 70% of the guest list are from dating apps. In her state, she started indiscriminately inviting anyone who would respond. Great! One guy shows up. He won’t stop telling me he’s from Boston. He will not let up about being from Boston.
Another girl shows up. She looks and sounds like Juliette Lewis. She’s a mess. Somehow in this mess, I end up alone in a room with this girl It’s just me, her, a terrible couch, and a 17″ iMac with a huge crack down the middle. She is searching for some song. She begins to repeat to me over and over about how vulnerable she feels.
She finds the song and grabs my hand to try and dance with her. I deflect as best I can and claim I have to use the bathroom. This is when I take it all in. The original girl is screaming at Boston man, calling him bad names because he won’t stop talking about Boston. The other girl is swaying like a ship at sea and another handful of people are addled out of their minds.
It is now 4 AM. I’ve had enough. I slip out the front door without saying a word. The streets are dead. Not a peep. I walk down the middle of the road back to my car. A coyote jumps out of the bushes. We just stand there staring at one another in the middle of the street. That was the best date I have ever been on.
14. Let’s Go Somewhere Private
It wasn’t really a date, but I hooked up with a guy (friend of a friend) who I met in a bar close to where my parents lived. As I was home from college and he was too, we couldn’t go to either house to “get to know each other better.” So, on the drive to drop me off, I suggested we pull in to a deserted parking lot in front of what looked like an automotive shop.
Not 5 minutes later while we were distracted, the cops pull up. They suggested we not choose the municipal garage where all the extra cars are as a place to have some private time. Oops.
15. Grocery Boy or Boyfriend?
I met a girl who was a friend of a friend and we swapped MSN Messenger details. We talked for a couple of weeks, got along great, and I suggested meeting up again. She was keen. Instead of going for a coffee, as I had suggested, she took me to a grocery store. She needed help picking up groceries for her Scouts for a camping weekend.
Basically, she had asked me out so I could help her load two full shopping trolleys of heavy stuff. I helped her load it into her car, thinking maybe we were going to drive somewhere to chat, or whatever. No, she just said “thanks!” waved at me, and drove off. On MSN that night she asked me if we were now boyfriend and girlfriend. I explained that we’d have to start dating first.
16. King Cry
I went on a date with a girl who I met in an online chatroom to see King Kong at the cinema. I was in my young teens and the ending absolutely shattered me even though I knew it was coming. I cried. Not a lot, but a couple tears. Her response crushed me even more. She noticed and asked incredulously if I was crying.
I just nodded and without saying anything further she got up and left. She never returned any of my messages after that.
17. I Thought I Was Being Smooth
My first night in Buenos Aires. I’m in a nightclub buying a drink. I hand the bartender about $20 in their currency. He’s saying something in Spanish I don’t understand. But I’m thinking one drink can’t cost more than $20 so what’s his problem? This incredibly smartly dressed, beautiful woman intervenes. She explains the barman is asking if I have a smaller note because he doesn’t have change.
No problem. We get to talking. I tell her it’s my first night in the city. She says, “Oh, you must let me show you around town tomorrow.” She puts her business card on the bar and pushes it towards me. It has her name, her number, and the fact that she’s an English Language Teacher. So, in what I think is an incredibly witty, flirtatious comeback I pushed the card back towards her and say, “oh, I don’t know. My English is already pretty good.”
She scoops the card back, says, “fine,” and walks away. I remember thinking, “Oh well, at least no one saw that.” Then I turned around and my friend is right behind me shaking his head like “What a loser.” When I told that story to some Argentinians I met later in that trip, they said not to worry. The woman had probably been a con artist targeting foreign tourists.
18. Oh, Look at the Time
A couple years after my divorce, I matched with an Indian (as in, not Native American) woman on OkCupid whose username included Pocahontas in it. Immediately, I assume this woman has a great sense of humor, and we have a couple days of great conversation and decide to meet up at a bar. It went so much worse than I planned.
When we meet, she’s much more awkward than she was via text, which happens sometimes, so I think nothing of it. That is, until about a half-hour into the date when she reveals that we hadn’t actually been talking on OkCupid and that her friend had been doing all the messaging because her friend didn’t trust her not to mess it up when she was talking to a guy.
I think that’s weird, but I figured I was there, so I may as well try to get to know this person. Then, maybe an hour in, she starts asking me about my divorce. I don’t mind a couple questions, but she starts grilling me. Then she starts lecturing me about how Americans don’t understand what marriage is actually supposed to be.
THEN she starts telling me about all of my moral defects that obviously led to my divorce. Finally, she also tells me that because I wasn’t financially secure (I was still working on my PhD), that I shouldn’t be dating anyway. Finally, I just cut her off, held up my wrist, pointed to my watch, and told her I totally forgot about something I had to do.
As I paid my tab and walked out, I realized I didn’t wear my watch that day.
19. We Fell Hard…
This was early in my dating days, so I can claim awkwardness beyond human reason. It was my first date with a guy who’d I’d known and crushed on for a while before we mutually agreed we should give dating a go. So, naturally, the whole hanging-out-with-the-intent-of-romance didn’t exactly go smoothly. It went horribly, actually.
When the “moment of magic” came at the end of the date, he bobbed left, I swooped right, and he managed to fall down some steps and I fell in a bush. We called it at that and there were no more dates.
20. Bleeding Heart
I have volatile allergies. My nose may have started bleeding during a New Year’s kiss with a beautiful girl I met that night. It may have gotten in her mouth by the time we noticed. And I guess she maybe ran to the bathroom and threw up. Please don’t look at me.
21. The One Who Got Away
I met a girl at Circle K, but I didn’t see her for a while, so I posted a Craigslist missed connections ad. I had never done anything like that. She actually saw it and responded. Mind blown. AND she wants to go on a date. So, we go out for drinks. I figured we’d just get drinks for an hour or two. My friend was playing a show that night at midnight that I had to go to.
It turns out we hit it off. Things are going well and we decide to go to another bar to get food. Get food and more drinks. We’re both very tipsy. I’m getting ready to say goodbye and head to the show. She says she really wants to keep hanging out and wants to come with. “Okay, great! I got to go though so I’m going to go close out.” “Okay! See you in a minute.”
So, I closed out both our tabs. Only later did I realize my mistake. This is a first date. You don’t normally handle someone else’s credit card on a first date. As I handed her back her card, she was quiet for a minute and then flipped out. She said I didn’t tip enough (I tipped 3 dollars on a $12 tab, she said she would have tipped $5) and that’s her money and none of my business.
Understandable. She told me she wanted to hang out again but had to go now. I emailed her a couple days later to see if she wanted to hang out some time again. Her response, “No. You messed up. Have a nice life.”
22. Have You Ever Kissed a Human?
He leans to kiss me just before I board my train and there’s the “kiss” that scarred me for a few months. He had both my lips in his mouth, sucking them, then he just stood there like that for a couple of seconds before releasing the suction. I was shocked and I quickly said bye and boarded the train. The next day I had two red marks around my mouth like I sucked out of a glass all night.
I had a crush on him for more than a year, but that experience quickly destroyed any attraction towards him.
23. I Kissed My Car and I Liked It
I drove a Volvo from the 60’s. The fuel line and filter would get clogged occasionally. On a first date, I pick her up. As we’re heading to dinner, the car dies. I pop the hood, knock out the crud in the filter, and then have to suck on the fuel line to get it flowing again. I wasn’t fast enough and end up with gasoline in my mouth and on my shirt.
She was understanding, but needless to say, she wasn’t impressed with the Techron mouthwash/cologne.
24. Splitting the Bill, Splitting up
Gay guy here. My date insisted on going to this expensive place, well, expensive to me at the time, being fresh out of high school and the closet and only working part-time for minimum wage. Everything went fine until the end of the meal when our bill came. His response stunned me. He just looked at me expectantly because he thought he was the more “feminine” one.
He was cute, but I immediately lost all interest right there when he curtly explained this. I went up to the hostess’s desk and asked her to split the bill. I then paid for my half and left him there. I blocked his number and never saw or heard of him ever again. I wouldn’t have minded paying if it weren’t expected, but the stereotyping was really off-putting.
Plus, the fact that I wasn’t asked nicely! He just handed me the bill without a word on the first date.
25. Know Your Angles
I went on a date with a guy and we seemed to hit it off. It went so well that I immediately texted him “thank you for a great time, hope to do it again soon” when I got home from our very first date. His response? An, er, intimate pic. I wouldn’t have been so offended if it hadn’t been possibly the worst pic I’ve ever seen. Socks on.
Messy bedroom in the background featuring Naruto posters and a serious collection of Goosebumps books on the shelves and to top it all off…it was possibly one of the smallest I’ve seen. However, he seemed pretty pleased with what little he had to offer. He asked me (to paraphrase) if I liked what I saw and I responded awkwardly that I’m not a fan of clutter or mismatched socks.
He blocked my number after that so I guess that shows me?
26. We’re Going Where??
I didn’t mess up the date. The date was just messed up. I met a girl at the local McDonald’s after school one day when I was 15. We talked and then exchanged numbers. She asked if I’d go out with her the next day. I thought she was gorgeous, and when she said I should dress up, I expected something special. She took me to her grandma’s funeral.
27. Don’t Mess With the Golden Arches
I got six months of prepaid Match.com membership, so I launched myself into the world of online dating. After a long time, I finally managed to meet a woman who seemed, at first glance, like she might be a nice companion. She was tall, slender, came across as being both fiercely intelligent and incredibly witty, and she wrote in a way that implied an appreciation for directness and rationality.
She also had impeccable spelling and grammar, for which I have a somewhat unhealthy fondness. I was smitten. We exchanged about a dozen letters before deciding to meet in person and when it came time for our date, I was feeling more than a little bit excited. We met at a local restaurant for lunch, ordered our food, and started amicably conversing.
If I’d known what would happen, I would have asked for the check with my meal. At first, we rehashed things that we’d already discussed. That quickly gave way to new topics, one of which was childhood experiences. This is where it went off the rails. “I can remember,” she told me, “going to McDonald’s as a kid, and ordering a Happy Meal just for the toy.”
“Me too!” I replied with a bit of embarrassment. “Fortunately, I grew out of that compulsion.” My date nodded her agreement. “But I grew out of that. Now, I can eat an entire Big Mac without stopping!” Her eyes brightened and she leaned forward. “What’s your favorite McDonald’s burger?” she asked. I said, “I don’t really eat at McDonald’s—”
“You don’t eat at McDonald’s?!” The urgency and the shock of my date’s interruption caught me off-guard. “No, not really,” I said again. “Not if I have a choice in the matter.” This was the wrong thing to say. From that moment on, I was treated to nothing but averted eyes and monosyllabic responses from her now.
Each time I tried to start the conversation back up, I found myself faced with a glare that would make Medusa jealous. Even my attempts at finding out why McDonald’s was so important to the girl were entirely fruitless. We parted ways immediately after the meal was over without her so much as saying goodbye. So weird.
28. All the Wrong Moves
I picked the guy up at his house. He didn’t introduce me to his sister and her boyfriend who we were conversing with. We went to movies, got to front of queue before he says, “I don’t have any money on me.” So, I paid. We went back to his house where I heard all about his ex and the amount of people he’d beaten up. He tried to get me to stay the night and refused to walk me out to my car. No second date for him.
29. There’s a Fire in My Heart
I was at a girl’s house and had to use the bathroom. Well, unfortunately, her family had candles in the windows for Christmas and the wire for the candle went right by the toilet. While I’m peeing, I sneezed, which messed up my aim. It set off a horrific chain of events. Of course, I end up hitting the wire and somehow starting an electrical fire.
Luckily, I was able to put it out, but of course I had to tell her what happened. I haven’t talked to her in a little over a year now.
30. Hit Me With Your Best Shot
I got hit by a car walking to her apartment. I bounced off the windshield and was thrown across the intersection. Probably because I was in shock, and in retrospect the driver was drunk, we didn’t call the authorities. Instead, I limped to the girl’s apartment. When she answered the door, she was dressed to the nines and ready for a big night.
I had to tell her I couldn’t go out because I’d just been hit by a car and probably should go to the hospital. She didn’t believe me. In fact, she looked at me like, “now I’ve heard every excuse in the book.”
31. Backseat Dater
She brought her best friend to a movie date. Date sat to my right. Best friend sat to my left. Awkward enough, but the friend’s bizarre actions made it even worse. He kept whispering, “C’mon man, make your move,” in my ear approximately every two minutes starting before the previews even wrapped up. Talk about a buzz-kill.
Worst of all, my date could hear, but seemed to find the whole thing to be perfectly normal. I did not make my move.
32. Can I Finish?
This guy was very attractive. He would occasionally come into my work. I never would have thought he would think I was attractive too. Well, he ended up asking me out. (Yay!) He arranged for dinner, but I would come to his place first. He immediately makes me a drink and also a shot of some type of liquor.
Not for us. For me only. He ends up trying to make out with me a short while later. And after a while of what I can only assume he thinks is that we’re playing a game of cat and mouse and him trying to shove my hand down his pants, I forcefully tell him to back off. He then asks if he “finish himself off.” He goes to the bathroom and has some, uh, alone time. We did not go on another date.
33. Rudely Interrupted
Ok, so I was driving this girl back to my house after a date and I decided to stop at my old middle school. I went to a private school that has a nice garden so we broke in and ate some strawberries. On the way back to the car, I noticed one of the windows to the English room was ajar. I climbed in through the window and unlocked the door for her.
The room was filled with couches, and after 40 minutes or so, we’re both completely in the buff. I’m kissing her neck when suddenly she says, “Wait! There’s someone at the door!” I turn around and sure enough there’s a shadowy figure at the window and the door handle begins to turn slowly like in a horror movie.
We grab nearby pillows to cover ourselves and brace for the inevitable. The lights go on and it’s none other than my old PE teacher (who’s married to the English teacher). He jumps and says, “Shoot! What the heck?!!” We throw our clothes on as fast as we can and then jump out the window that I came in through.
34. Love Is Blind
My aunty set up a date for me. I am half Asian and half European, and my family wanted me to date and probably marry this girl because she comes from a rich family. So, we met at a restaurant and she brought her brother. He brought his girlfriend. I went there with a cousin and he thought the whole thing was hilarious.
We introduce each other but its loud and they mumble so I don’t understand their names. I decide not to ask them all for their names. I didn’t want to be rude. So, I talk to this girl and she is educated and good looking as well. I start to think: Hey, this wasn’t a bad idea. I actually like her and we seem to be on the same wave length.
I start to flirt with her and she seems to like it. Then suddenly the brother says something and they just leave without saying anything. I am totally confused. Then I learned the awful truth. It turns out I was flirting with the brother’s girlfriend the whole time and I never even looked at the girl I was supposed to date except when we introduced each other.
35. Drinking Alone
I flirted with a cute bank teller for weeks before working up the nerve to ask her out. I didn’t realize she was super religious, invited her to a Mexican restaurant, and ordered two margaritas. When she told me that she doesn’t drink, I said, “That’s ok. These are uhh… these are both for me!” She told me I wasn’t Christian enough for her and I agreed. And there I sat, drinking two margaritas alone.
36. Fistful of Nothing
He showed up late to the restaurant and had me wait outside while he finished a smoke. We went inside and had drinks waiting for a table and when our table was ready, we settled up with the bar and he pulls out this massive fistful of change and tips the bartender in dimes and nickels. He spent all dinner talking over me about Magic the Gathering and his job hunt.
After dinner, I had to walk 4 blocks back to my car at night alone because he had to run to make raid time. Any one of these things alone would have been enough, all four made it the worst date I ever had.
37. Inappropriate Dad Jokes
This girl’s father had just recently passed on, so I invited her over to make her dinner and console her. We make dinner and we are talking about stand-up comedians and she tells me she’s never seen Louis C.K. so I say we need to watch one of his standups. Well I turn on one randomly and the first 25 minutes are dead dad/parent jokes.
38. The Zombie Apocalypse
I’d been interested in my cute co-worker for a while but we were just friends and that was fine. Still, we hung out a lot and eventually one night we got drinks after work and things escalated. Fast forward to later that night. We’re both asleep at her place. Now, I hadn’t been sleeping well all that week partially because of her dragging me out with her.
And when I’m sleep deprived, I have very strange dreams and am prone to sleep walking/talking. In my dream I’m walking done this tunnel, like a metro tunnel. I see this girl on the ground crying. She’s got no clothes. I ask her what’s wrong and she lunges at me. She was a zombie or something. She wraps her corpse arms around me and I throw her off and start yelling.
That’s what I was seeing. I was fighting for my life. In real life, it was ten times worse. What had actually happened outside of the dream was she tried to cuddle with me and I responded by freaking out and literally throwing her out of the bed. She screamed and that partially woke me up but I’m still mostly in the dream.
She asks me what’s wrong and I just start yelling things. “Who are you? Where’s your clothes? Get away from me!” I woke up fully as she was storming out of the room. She thought I was trying to be a jerk, I suppose. I was absolutely mortified. No joke, I felt awful. I thought I blew it. Once I went out and explained what happened, she thought it was hilarious and came back.
39. The Olive Garden Tragedy
I was like 17, and a buddy of mine was trying to get with some girl from a few towns over. She’d only come to my place to hang out if her friend could come too. Fine. So, they come over and we talk and I really like the friend. We hit it off and when they left, she actually gave me a kiss! I couldn’t believe it.
I get her number and her IM name and all that and I proceed to fall pathetically in love with her. I mean, we hadn’t gone out ever, but man was she the best. Fun. Out of my league cute. So, she agrees we should go out on a date. Sweet! On Saturday night, we went to the Olive Garden, because I am a classy 17-year-old dude.
There was a wait, so I put my name on the list. And we sat there, and waited, and waited, and waited some more. I remember distinctly that she started looking through the phone book (we sat near a pay phone) for funny names to kill the time. I was, and still sort of am, the type of person that doesn’t want to be any trouble, so I felt awful asking the hostess what was up.
After what had to be at least an hour we just left. Nobody else was in the waiting area at that point. I was so embarrassed.We talked on the phone a few more times but I never saw her again. I sent her at least a handful of “you broke my heart” type IMs. It was without a doubt the most cringe-worthy stretch I ever had with another person. Blech.
40. Take Me out to the Ball Game
I was 17 years old and my girlfriend told me weeks in advance that she was planning to take me to dinner and a baseball game. The night before the big day, she reminded me, “Be ready by 4 PM, I’ll be picking you up and you don’t have to worry about anything.” The next day came, we spoke earlier in the day and I was stoked to go to the game. 4 PM rolled around.
I somehow fell asleep on the couch and slept through her pounding on the front door. When I finally awoke, it was about 4:20pm, my girlfriend was very upset, I felt like a pile of trash in more ways than one. I felt terrible for not being on time. We’ve been married nearly 10 years now. That day has come up a couple times and we laugh about it.
But I know she still feels a little upset about the day her boyfriend messed up the first date she planned.
41. Can You Hear Me Now?
It was a blind date. Her mom worked with my mom. I saw a picture of her, she’s very pretty. I called her and set up a date. The phone call left me feeling like she might not be into it. This continued after I picked her up. Most things I said got an unenthusiastic response of a drawn out, “Yeahh.” I couldn’t figure it out.
Want to do this? Want to go here? Want to go there? “Yeahh.” When I learned the truth, I nearly passed out with embarrassment. It turns out that she was mostly deaf. Even worse, nobody (including my own mother) told me. I ruined it by not knowing she had a hearing problem. I still feel bad about it. I could have done better if I had known.
42. Destiny, Tears, and Soiled Pants
Okay. So, I went on one date with a guy that I met on Facebook (mutual friends). Now that I think back on it, he may have had some serious mental problems. He was really sweet and handsome, but towards the end of the date he said something like, “I really think this is destiny like we are meant to be.” And I just laughed along with it and said, “cool,” or something.
He then said, “I had a dream we got married and I think it’s going to come true.” And then looked at me like it was the most romantic thing a guy could say. After a long silence, I burst out laughing and he is visibly upset. He then begins to shake and start sobbing. I say something along the lines of “oh my god, I’m so sorry. I just like to take things slow.”
“You caught me off guard with that comment!” He shouted back through hot tears, “You caught my heart off guard!” I sat with him for a while longer with the only sound between us being his quiet sobbing. Oh, but it gets worse. He suddenly stops and I smell the most potent, disgusting smell I think I’ve ever smelled. He looks at me accusingly and says through his tears, “I just pooped myself.”
After stifling a laugh, trying to comfort him, and sitting next to a wailing, soiled 26-year-old man for a few more minutes, the smell became too much so I mumbled an excuse and left him there. In a pile of his own poop and tears. A few days later, I received a Facebook message from him apologizing for his “little accident” and informing me that I “still drive him crazy.” I blocked him.