Bad dates. Is there anything more uncomfortable in this world? Meeting a weird person, even one that might be cool but find out it's totally wrong? Or blind dates that blindside people with crazy revelations? Like the girl that was dating her brother? Or the woman that thought going on 10 Craigslist dates was a good idea?
Michael Che Makes It VERY Awkward
“Michael Che (comedian and anchor for SNL’s Weekend Update) ruined one of my first dates!
I go to a lot of standup around NYC and I happened to see him trying out material at two different free shows in the same week. He was doing this crowd material bit about adult videos where he would pick a guy in the front row and corner them and ask them what they searched for when they looked for smut.
The first time I saw him doing it, he just would not let up on this poor guy, the guy didn’t want to answer and kept saying, ‘I don’t know’ or ‘I’m not sure, but Che kept asking, ‘Come on, man, I KNOW you know. What do you mean you don’t know?’ The guy never relented and said anything out loud but Che kept pressing him for seriously the entire show, like he kept going back to this one poor guy.
Cut to later in the week, I’m taking an OkCupid date to a standup show, I sit in the front and Michael Che turns out to be the surprise headliner. The second I see him on stage, I freaking know it’s gonna be me, I know he’s gonna do the bit again and I’m sitting front and center. My brain is racing trying to think of a good way to get out of this awkward situation, ‘don’t say bondage, don’t say bondage’ (this was a very casual date and I had not been speaking to this poor girl for very long, plus I’m already a weirdo).
Within like 30 seconds he turns to me and asks, ‘what about you, sir, what do you type in the search bar when you look for smut?’ and I think, ‘okay, just say the most innocuous harmless kink possible.’ I stall for a second with a ‘who me?’ and he repeats the question, so I blurt out without thinking, ‘Redheads!’ Whew, fine, I’m in the clear. Awkward situation handled. Except I forgot that my date was a redhead. Of course he immediately picks up on that. ‘You know the girl sitting next to you is a redhead right?’
I reply, ‘Yes, we are… actually… here on a date.’
He said, ‘Wow, this has never happened to me during this bit before,’ then cut me some slack and moved on.
In the larger scheme of things this probably wasn’t that bad, and the date wasn’t going spectacularly anyway, so it wasn’t like a huge loss, but it definitely made things very awkward for the rest of the evening. It was kind of a relief when she said no to a second date because then I immediately texted her back and was like ‘That’s fine OH MY GOD CAN WE TALK ABOUT HOW CRAZY AWKWARD THAT WAS?’ and she was like, ‘I KNOW!!’
That’s funny, but as someone who also does comedy as a rule I never try to be funny when somebody onstage is talking to me as an audience member. It works out for the person every once in awhile… but usually the comedian is looking for a genuine response from someone so they can do their material and it kind of throws them off if the response is smart-alecky. It’s just more polite to let the comedian onstage be the one telling the jokes.”
A Player Gets Caught
“Once, I talked to a girl on Tinder that I hit it off with pretty well, and we made plans to meet up later in the weekend. We’ll call her Sarah. The next day though, another girl that I’d talked to, that we’ll call Sophie, told me she’d be out at a bar close to me. She told me to come join her, and bring a friend. So I brought my roomie, and went to meet Sophie.
When we got to the bar, I spotted Sophie sitting there with another girl, whose back was turned to me. I went up, gave Sophie a quick hug as I sat down next to me, and motioned for my buddy to sit on the other side with the other girl. It was only then I actually looked at Sophie’s friend. First noticing the intense stare I received from over the table, I realized the girl was Sarah, the girl I had made plans to meet up with the following day.
I could see she was equally taken aback as me, and for what felt like an eternity we sat there with the biggest deer-in-the-headlights-look before the silence was broken by Sophie, saying ‘Hey, this is my bestie, her name’s Sarah!’ Which led to us nervously shaking hands, exchanging names, not knowing what else to do.
Already having shook hands as strangers, neither of us really knew how to proceed, not wanting to mention the elephant in the room, since Sophie and my buddy had no clue what was going on.
It actually did go alright in the end, my roomie and Sarah ended up talking, and hitting it off. It seemed we’d reached a silent, yet mutual agreement not to mention the glowing mammoth in the room.
In the end, the girls actually ended up going back to our flat with us, spending the night. Sophie and I dated for almost two months, but things did not work out, as they sometimes do. We’re both in happy relationships now though, so it all ended well, I think.
I only told my roomie the reason I had looked so confused after they had left the following day. But yeah, that was such a strange date, which somehow worked out.”
Rich, But Wasted
“About eight months ago, on a Tinder date, this girl suggests brunch at trendy restaurant in Dallas. I pick her up at her apartment nearby. She’s not ready, so she buzzes me in and I wait in her place. Her apartment is beautiful, lots of high-dollar stuff, no roommate.
We go to the restaurant at 1 pm and she drinks an entire bottle of bubbly by herself. We leave and in the car, she says she wants to stop by a shop nearby. I park in the parking garage and get out. I look for her and don’t see her. I hear a noise, so I look around my car and she’s squatting next to the wall peeing on the ground.
We go into the shop. She takes a few dresses into the changing room and tells me to come over. I stand outside the changing room and she grabs me and pulls me inside. She completely undresses, gets in the clothes, asks me what I think, undresses, gets in more clothes, etc…
She takes about $1,500 worth of clothes to the counter and tells the cashier she really has to pee. Cashier says sorry. My date begs, so cashier relents and takes her into the back, but it’s too late. The damage is done. She also buys a new pair of pants.
On the way back to her apartment, she answers a call and starts talking in a foreign language that I can’t place. Couldn’t even guess the continent. She’s very nervous and upset. She hangs up and tells me she has to go to her other apartment – in the same neighborhood. She asks me to go in with her. We go into her apartment which is also completely beautiful and belongs only to her. She has an awesome telescope that I start playing with. In the mirror, I see her open a safe and put something in her purse. She tells me we need to leave and asks me to take her to my house.
We go to my house and she instantly passes out and stays passed out for about 6 hours. She wakes up and wants Dairy Queen. It’s closed and she starts crying, so I take her to Sonic instead. She gets a cheeseburger, a chili dog, cheese fries, and a sundae. We come home, she eats it, immediately throws up, and passes out on my couch. I read and go to sleep.
The next morning, she asks if she can stay and watch football. I tell her I have plans and need to take her home. She says she can’t go to either of her apartments. I tell her too bad, I have plans, and drop her off at the apartment closer to me. She texted asking when we could see each other again, but I never responded.”
This Guy Was WAY Too Bold
“I got setup with the son of one of my mother’s friends from our Synagogue.
He picks me up at my parent’s house (we were 17). Not even 10 minutes into the date, we were literally driving to a restaurant, he point blank asked me if I would rather give him head now or after dinner. To which I replied, ‘Excuse me!?’ Perhaps I misheard him?
And he smiled and replied slowly, as if I was hard of hearing, ‘Are you going to suck me off or what?’ At that point, I yelled at him to go eff himself and pull over. I kept yelling pull over as loud as I could. He started to freak out, but pulled over. I got out of the car and started walking home.
He followed next to me for a few blocks with the window rolled down imploring me not to tell his mom or my mom. I ignored him and refused to respond so he got frustrated called me an ugly witch and drove off. I got home about an hour later as I walked all the way home – this was before cell phones – and told my mom what happened and she was justifiably mortified. She, in turn, calls his mother and tells her exactly what happened. The guy’s mom didn’t take it well either and tried to put the blame on me, that I ‘asked for it.’
Needless to say, my mom never talked to her again.”
A Parade Of Parties
“I was going to have a second date with this girl. She knew of three parties happening on the same night, so she suggested that we hit all three. Sounded good to me, so off we go.
At party one, her best friend from college is there that she hasn’t seen in four years. They immediately run off together, and I’m left with the friend’s boyfriend having a drink. I think to myself, this is no big deal. She hasn’t seen her friend in a long time, and the night has a lot more to go. She comes back after a while and suggests we head on to the other party. Great!
Arrive at second party. My date immediately runs off with some other friends. Like, ‘Tim, oh my god, how are you doing,’ and dashes across the party to find him. I slowly follow behind, but then they keep scurrying on to talk to other people without the girl making it clear that she wanted me to come. I feel really awkward because she doesn’t introduce me or say anything about me. I’m just an awkward guy there that no one knows. I get tired of that and go to the bathroom, where I find that the door has been ripped off its hinges. I find a screwdriver and fix the door before using the bathroom. Fast forward 30 minutes, my date finds me and suggests we go to the final party. But this time, her friend Tim is going to join us. Okay…
Arrive at third party. As soon as we walk in the door, Tim says he needs smokes, and the girl and Tim run out for smokes and leave me at this new party with all these other people I don’t know. They are gone for 45 minutes, by which time I decide that this date isn’t working out and I should just go home. When my date comes back with smokes, I tell her I’m leaving and she FLIPS OUT. She starts screaming at me in front of everyone about how she was going to hook up with me later and how I ruined everything. Then she proceeds to scream, ‘You’re not leaving me; I’m leaving you,’ after which she bolts out and slams the door.
Then everyone at this other party, whom I don’t know, is staring at me while my date, who brought me there, has abandoned me.
Someone eventually comes and offers me a drink. I stay for another hour and laugh it off with the people at the party. I am still friends with some of those fine people today.”
“I went on an OKCupid date once.
The girl and I drove past a mattress and box spring hand wrapped in plastic.
She asked and then insisted that I stop and get the box spring/ She wanted me to put it in my truck and then help her put it in her second story walk-up apartment.
I politely said no, I do not think that is a good idea. That there is a pretty solid chance of bed bugs because sealing an item is what you try first when you have those nasty little things.
She was having none of it.
I refused. She started crying, telling me that I don’t know how it is to not have things and that it is easy for someone born with a ‘silver spoon in their mouth’ to write off a free box spring. She didn’t know me at all and made these assumptions based on who knows what. It was hard to hear since I came from absolutely nothing and worked my tail off to get to where I am.
We pulled into the restaurant and she finally settled down a bit. We ordered our food.
She answered a phone call at the table; it was a friend that had an extra ticket to a festival. She really wanted to go but had just started a job serving food at a restaurant. I suggested that she not call her boss and ask for the days off. I worked in the restaurant industry when I was younger and I knew that her supervisor would not let her call off from her fist weekend. She called her work anyway. She started crying when her boss said ‘no.’ I felt bad for her boss, not her. Her boss fired her on the spot. Did I mention that her roommate had just moved out, and instead of earning money to make up for her missing rent, she chose to try to go to a music festival that weekend?
I paid the check with both of our meals still steaming and untouched. On the way back to her house, we reached a stop sign. She jumped out of my truck and ran towards a trash pile. She came back with a day-glow painted end table and threw it in the back of my truck. When I got to her house, I said nothing. I just put it in park and hit the unlock button.
She then took both of our togo bags and ran off with her ‘new’ end table. I was actually stunned. I felt bad, she was really pretty.”
His Friend Should Have Known
“My freshman year in college I had a crush on a girl from my high school. When I asked her out, she informed me that she only dated women (I am male). She insisted that we should still be friends, she just didn’t roll that way. She offered to be my wingman and I gladly took her up on the offer.
A few weeks later she had set me up on a semi-blind date with one of her friends (we’ll call her Monica). The three of us met at Arby’s (because we were fancy) and my friend tried playing matchmaker.
‘Bob (that’s me) loves theatre and so do you, Monica!’
‘Monica loves music and so do you, Bob!’
The date was going fine, so my friend decided to leave Monica and I alone. We talked a bit more and decided to go see a movie. I didn’t have a car at the time so I hopped in Monica’s passenger seat and we went on our way.
That’s when things got weird.
About two minutes after leaving Arby’s, Monica receives a phone call. She says it’s her roommate and she needs to answer it. She picks up the phone and I hear a man’s voice. I was a bit surprised, but it’s not too unusual for a girl to have a guy for a roommate. Monica and her ‘roommate’ get into some kind of argument, and she pulls over to a gas station. Another car pulls in right beside us. Again, I didn’t think anything of it at the time.
Monica turns to me and says, ‘I need to go talk to my roommate. Just wait here for a minute.’ I assume she just wants to be on the phone in private, but what happens next will shock you! Monica gets out of the car and goes to talk to the driver of the car that pulled in next to us. This is where I start to freak out. What are the odds that her roommate happened to pull up right beside us?! I hear a bit of yelling and then I start thinking about an escape plan. At this point, Monica opens my car door and says, ‘Hey, I’m really sorry to do this but my roommate is going to have to take you home.’
Now, this is the part of the movie where someone in the audience screams, ‘Don’t you go with him, now! That’s how you get killed! White people always going with the strange man thinking everything will just be a-okay!’ I wish I could say I got smart, said, ‘No thank you, I’ll just walk’ and went home.
But I didn’t.
With some combination of confusion and curiosity, I get out of Monica’s car and head into the passenger seat of this stranger. We’re in my hometown, so I know if he goes any direction he’s not supposed to I can just bail out of the car and run to freedom. The guy was pretty big. I was 6’2″ at the time and he was significantly bigger than me, if that tells you anything. I don’t remember his name, but we’ll just call him Ross. Anyway, Ross starts driving back to my dorm and we’re sitting in awkward silence for most of the trip. Eventually, he says, ‘So how do you know Monica?’
I knew something fishy was happening, so I wasn’t about to say we were on a date. I just say ‘Oh, we have a mutual friend.’ and hope Ross doesn’t get suspicious. He just nodded his head and kept driving. Apparently Ross was resolving some anger in his head, because out of nowhere he starts talking as if we were in the middle of a much more personal conversation. ‘Yeah…. A lot of people at our church are upset that Monica and I live together. I think they’re just assuming we’re ‘sinning’ all the time or something. It shouldn’t even matter since we’re engaged, but it’s still annoying to hear stuff like that, you know?’
I just nod my head as I realize what just happened. Apparently my lesbian friend set me up on a blind date with an engaged girl, and her fiancé came and picked me up to take me home.
I was silent the rest of the night. I told Ross the wrong dorm so he wouldn’t know where I lived, and I got out of the car and just walked around campus for a bit. It was definitely the strangest date I’ve ever been on.”
He Starts The Date With A Lie
“I had just moved to London and met this guy on a dating website, but he was generally not my type. Still, I was fresh out of a long-term, damaging relationship and trying to meet new people yada, yada.
On our date, he takes a call from a girl and he says to her – ‘Oh, I’m just in the pub with (male roommate’s name).’ I can hear her on the other end getting worked up about something and him telling her to calm down. Alarm bells already ringing.
He hangs up the phone and says ‘that was my fiancé, but not a real one, just one i’m with for her visa’ At this point I’m already thinking ‘oh shoot.’
He continued on with his excuse ‘She also lives with me.’ In his 2 bed apartment with this other roommate. Cozy.
‘Oh yeah, I should probably tell you I’m getting married in three weeks.’
At this exact point, I just said, ‘Well, I’m going home’ and start pulling on my coat.
His reply was even more classic: ‘Do you want to help me buy groceries first?'”
She Was Super Sketchy
“I went for a meal with this girl I met through a dating app and it was going really well. We started talking about movies and then we decided to go to the cinema to go watch the movie Inception.
She said there was a cinema nearby but I didn’t know the area at all, so I used the GPS on my phone and she held it and directed me. Once we got there we started walking inside, I realized I didn’t have my phone in my pocket. I said I must have left it in the car and started to walk back to get it. She was trying to get me to leave it and saying we would miss the film but the phone was only about a week old so I was really paranoid about it. We checked the car for about 10 minutes but we couldn’t find it. I asked her to check her jacket and her bag but she said it wasn’t there.
A couple parked next to us so I asked them to ring my number because I couldn’t find it. It started to ring and it was obviously coming from my date’s handbag. She took it out and said she must have missed it. I thanked the couple and locked my car and as I turned back around she was walking the other way. I ran to catch up and asked what was going on but she was very dismissive and was barely talking.
I had asked her and she said she called it. I didn’t see her dial the number and I only had 1 missed call from the guy that called my phone. When she found it in her bag I thought it was weird, but it wasn’t until she started walking away that I suspected her trying to steal it. Before that I had no reason not to believe her, I was more focused on finding my phone.
That’s when I realized it wasn’t an accident and just left her to walk home alone.”
Don’t Meet People On Craigslist
“So, a few years back, I lost a bet with a friend. The loser had to go on 10 Craigslist dates. The rules were as follows: I had to post a personal ad in the women seeking men. The ad had to be simple. I had to correspond with the people who responded and if they asked me out on a date I could not refuse (up to 10 people). Once the ten was met, I was off the hook.
I don’t remember the exact wording of the personal ad but it said something along the lines of ‘young, professional woman seeking young professional man for light conversation and friendship.’ Here is date #1:
Enter the crazy.
So date #1 was with the first man who responded within 2 minutes of the ad being posted (yikes). He responded saying he had just moved to the area was 29-years-old and worked as a lawyer. He too was looking for friendship and to meet people in the area. We exchanged emails back and forth, and in the third or fourth email he asked if I would like to meet for coffee. According to the rules, I had to accept. So I set the meet up with him at my local coffee bar. I asked to exchange pics so we knew what we looked like but he evaded and instead described his clothing. Red Flag.
I went to the meet up accompanied by a close guy friend who works as a bouncer. He sat a few tables away for support and in case things got crazy.
I drank my coffee and waited. I told him I would be wearing a red cardigan and he said he would be wearing a blue button down. Before I knew it, an older gentlemen (late fifties, early sixties) sat down at my table asking me if I was the girl from the Craigslist ad. I confirmed I was and he introduced himself as the man I was supposed to meet.
I immediately called him out on lying about his age to which he replied, ‘Well, in my head and in my heart, I’m 29 so what’s the difference?’ He then admitted that he was not a lawyer and that he was a retired sanitation worker. I asked him why so many lies? His response, ‘I always wanted to be a lawyer and you said you wanted a professional so I figured it was a good match.’ He started getting upset that I was asking him so many questions and that I was implying that he was liar.
At that point I asked him point blank: ‘What were you expecting from this? What did you think would happen when I met you and realized you lied about everything you told me?’
He responded, ‘We had so much in common, I just thought you were already in love with me and you wouldn’t care.’ I was speechless. I didn’t even want to know how he had the idea I was in love with him. I was starting to get super uncomfortable.
I looked over to my friend and implored him to save me, but he didn’t notice my distress at first. The gentlemen saw my distress and smiled while he asked me, ‘Are you uncomfortable?’ He started leaning over the table as if to grab my hand, but instead grabbed my coffee and started chugging it while making direct eye contact with me. I sat there stunned and unsure of how to react. I looked over at my friend again, and thank god he saw my look that time. He immediately came over and pretended to be a friend who happened to be at the cafe.
I stood up to greet him and after a moment of chatting, made an excuse to use the bathroom. My friend caught the drift and as I went to the bathroom, I turned and I booked it out of there and he quickly followed.
Thus ended my first Craigslist date in all its weird and uncomfortable glory.”
She Was A Real Pig
“Met a girl online, talked her up, and while she seemed a bit immature, thought heck, why not? She casually mentioned she really liked pigs. What she meant to say was she was obsessed with pigs. OBSESSED.
We go to one of the best restaurants in the area for a first date (bad idea). Sometimes pictures are from someone 10 years prior, or the person hides things, etc. But that wasn’t the problem. She looked just like her pictures. But I didn’t even have to have seen her first, because everything else gave it away.
She came in a giant T-shirt that had a sparkly pink pig on it. Earrings? Pig earrings. Bracelets? Yep, pig bracelets–I swear her dad might have been Homer Simpson. She had this headband on with a little pig on it. Her shoes? Yep, pigs on the front of the toes! But best of all? She had a GIANT (or at least it seemed giant) pink purse with the face of a pig on it.
You could not stop seeing it once you did. And I’m sure everyone else in this nicer/classier restaurant saw it too. I felt overdressed with her but under-dressed with every other couple there. It was beyond embarrassing. For some reason which I have to convince myself was politeness not stupidity, we still had dinner. It was the fastest dinner I’ve ever had at a sit-down place.
I practically blurted out something like, ‘Oh, you really do like pigs…’ to which she started giggling (oinking?) and going on about how everything she has is pig themed. Then she wouldn’t stop, and it became the dominant part of the conversation. There were a dozen other things that made it a train-wreck, but these were the clinchers to a solid 0/5 date. I remember afterwards consoling with a friend of a friend, because I had to tell someone; and then I promptly buried this as my worst date.”
She Dropped All The Hints
“I met this girl online and the way the conversations went, it was always friendly, getting to know you type banter. After a few online conversations, we meet up at a bar by her. The plans for the evening were to have drinks there then go play Donkey Kong Country at her place. Being the oblivious male I am, I genuinely was excited to play some DKC on Super Nintendo.
We meet up at the bar and things go fine. I wasn’t really attracted to her at all, but she was nice and we had an alright time at the bar. Eventually, we get back to her place and start watching TV. I look around and don’t see a Super Nintendo. I thought maybe it was in her bedroom. I don’t mention it because I don’t want to be rude. She makes some drinks. We’re watching some show one the History Channel, when all of a sudden she looks at me with murder in her eyes, ‘Are we going to stop playing games?!’
I look at her, smiling, trying to play it off, ‘Do you mean Donkey Kong Country?’ She really didn’t appreciate that. She scoffs and then proceeds to chide me about how guys are always wanting to play games and want to hook up. I told her the only game I was wanting to play was DKC. This is when it got weird. She gets up off the couch, calmly, walks to the kitchen and pulls a butcher knife out of somewhere. She just stands in the kitchen, still with the look of murder in her eyes, and stares me down. She doesn’t move at all, just staring with the butcher knife at her side. I look back for what feels like a few minutes, and then I jump up and dash for the front door.
I didn’t even bother closing the door, behind me I hear the door slam hard, and she’s shouting at the top of her lungs, ‘YOU PRICK, PLAYING GAMES, EFF YOU!’
So a night of what I was hoping to be relaxing, friendly conversation, and Donkey Kong Country, turned into my ‘maybe I could have been murdered’ dating story.”
Her Boyfriend Was Her…What?!
“I’m a dude. I was about 16 at the time.
My female cousin tried to hook me up with her ‘nice friend’ whom I had shown interest in after meeting her at a family gathering. We text and talk on the phone for a couple weeks and later, we agreed to meet at the mall.
We get to the mall and the girl shows up with another guy, who apparently is her boyfriend. Yes, she introduces him as such and all that. Apparently, he was her ride to the mall. My cousin didn’t think this was odd. I was highly annoyed the whole time because the girl is really fine. We walk around the mall, the girl, my cousin, and myself. The boyfriend waits in the car. The girl tries to get me to buy her stuff in the mall, I lie and say, ‘Oh, I don’t have it like that right now.’ She tries to hold my hand, asks me to get her something at the food court, the latter I give in and do. I tell my cousin I’m ready to leave. And the girl goes, ‘You’re cute. And sweet. You should totally be my guy.’
I was dumbfounded, ‘Don’t you already have a bf?’
‘I could have two! Besides, he’s just my brother. I don’t have to commit to him.’
My jaw drops, I just tell her no thank you, and leave quickly. My cousin asks what’s wrong, still not seeing the problem with her friend’s relationship status.
I’m still weirded out by that to this day.”