What’s Your Most Awkward Date Story?

My husband and I dated long distance in college, but by his second year, most people knew he had a girlfriend (it was a small school, he was in a fraternity). We both had lots of male and female friends, so he didn’t think it was unusual when a woman in one of his classes asked him to get lunch together until she insisted on buying his lunch. He decided not to overthink it, and said he would get the next one. As they sat down, she said ” wow, you’re confident, you already think you’ll get a second date.” My husband choked on his food a bit, and awkwardly (but kindly) explained to the woman that he was in a relationship, and had been unaware that this was a date. She started crying, saying that it was the first time she had asked someone out without looking them up on the internet, because she wanted a more “organic” experience. My husband calmed her down, and insisted they finish their meal so they could at least be friends. He paid her back for his lunch, and went out of his way to be nice the rest of the semester. A few months later, we were on campus grabbing snacks before a movie marathon with his friends, when she approached me and apologized for making my boyfriend into an “unwilling cheater” and hoped I forgave him. I made the comment that he didn’t really cheat on me, and I actually thought the situation was a little funny. She was super nice about it, and actually attended our wedding!

Went on a date with a girl I met at a dance club. We met up at a bar, had a few drinks…she had a lot more than me and was soon pretty drunk. We decided to head to a new spot. On the way, she insisted she had to stop somewhere on the street to pee. We were 2 blocks away from the next bar so I told her to wait, but she decided that was too far and went to an alley. Instead of hiding behind a dumpster, she proceeded to drop her pants 3 feet from the sidewalk in full view and made me hold her hand while she peed. I was obvi done with the date then, but worried about leaving her alone and she refused to go home. We went to the next bar and had water while she tried to pressure me to have sex in the bathroom. After that I got her a ride home and that was the last we saw of each other.

I decided to try online dating because it was new in the early 2000s. I was living paycheck to paycheck at the time and on that day, my account balance was abysmally low. I agreed to meet my date at a trendy sushi restaurant that just opened; he insisted on paying. I had taken a cab from my city apartment and had just enough cash for the cab ride home. I met the guy, a “musician”; the date was going fine, not great, not terrible. We both ordered a drink and a roll of sushi and had decent conversation. Towards the end of the night, I went to the ladies’ room, and he said he would pay. When I came back, he was not there, yet the bill (over $100) was sitting at our table – unpaid! I literally could not cover the check myself, so I left my cab fare as a tip and walked out, red hot with anger and embarrassment. It was going to be a 45-60 minute walk home in the cold, dark, and potentially dangerous city. Fortunately, a taxi saw me and picked me up. I told him what had happened, tearfully, and he took me home for free. I never went on another date without being able to afford the whole thing myself (including transportation).

My worst date with from Tinder… he seemed normal, was a lawyer, seemed smart and witty. We chat a bit and agree to a date. First off, he ends up arriving more than an hour late and shows up notably drunk from a child’s daytime birthday party (??). Then he proceeds to tell me that he figured out my last name and where I worked and that he used to date my co-worker – who I very much like and is an amazing woman. He then let me know that they didn’t work out because she was too prude (again, sir, I told you she was my friend…). He THEN informed me that he requires sex every day and based on my face (of total shock and maybe confusion as to whether I was actually hearing what I was hearing – like this was 10 minutes into a first meeting), it didn’t seem like it was something I was willing to do (after arriving drunk and swearing, I decided that was never going to happen anyways). Then, to further elaborate, he let me know he’s not some total sex weirdo and that, in fact, “missionary every day is fine”. Like most other stories in the comments, I am embarrassed to say that I did end up staying for at least an hour more trying to figure out a graceful way to extricate myself. The waitress looked like she felt sorry for me. But “Missionary Every Day” became somewhat of a single woman rallying cry among my girlfriends. Also, based on texts from the next day, he thought the date went super well… I guess he decided maybe I could in fact handle missionary every day…

This is the sweetest story! What a good man you got <3

I got asked out in a doctor’s office…while I was with my mom! He had a big smile and was a very smooth talker. The big red flag should have been that he worked in a women’s shoe department. We went out a few days later, he picked me up (was late) and we proceeded to the fancy Mexican restaurant in the nearby beach town.

Little did he know that my sister and her friend decided this guy sounds like a creep and booked a table (with my consent) at the same restaurant. We sat down RIGHT NEXT to them.

The date went on…and on. He was very nauseating and wouldn’t stop talking about his high school football career. I get a text halfway through and it was my sister saying “meet us in the bathroom”. I excused myself and met them – they said I looked incredibly miserable – which I was. We decided I should end the date earlier than later and NOT feel bad for doing so.

I took their advice and after dinner said “I was busy the rest of the summer so no I cannot go out with you again”. He laughed. I never saw him again.

To this day I’m so thankful for my sister and her protective and hilarious intervention. She has since passed away and I will always treasure that date for what it was and what it wasn’t. Thank God for sisters!!!

A few years ago, I accepted a date from a man my friend had set me up with. He picked me up and on our way to eat he played Celine Dion power ballads the entire ride. After eating, we went to go see a movie. an Indian movie. which was about 4 HOURS LONG. He kept trying to put my head on his shoulder and the scent of bare scalp (he was bald) kept making me want to gag. I kept excusing myself to go to the bathroom. The entire date he kept asking me if I was his boo (“You’re my boo right?”) On our way back to my house (he was going to drop me off and definitely NOT get invited in) he began to complain about how he would get blue balls and if I could just touch his little man to help him out medically. Ok, our date was officially over now. I told him to drop me off at some random gas station, when he asked if I would like to meet his parents now because he was sure I was the girl he was going to marry. I said no and walked the entire way home. The next day I received a text from him saying I need to lose a few pounds from my stomach because otherwise how would we perform all the sex positions he had in mind. Block. Coincidentally, I am no longer friends with the girl who set me up with this walking disaster.

These stories are amazing, hahaha. I love this post.

A few years ago I was feeling extra inspired to find a relationship, and I was going out on a ton of dates via match.com. I set up a dinner date with a promising guy. I arrived at the restaurant first and decided to just go ahead and get a table.

A couple of minutes after being seated, I looked up and I saw my date coming toward me. I got up and said “hello!” and gave him a big hug. I sat down and asked him how his weekend was going. He just stood there and said, “good!” with a smile on his face, and then intently asked me how I was doing.

I remember giving an answer and thinking, “why isn’t this guy sitting down?”

We chatted about something else for a minute or so and then I suddenly realized….. this guy is not sitting down because HE IS THE WAITER. He resembled my date, but he was NOT the guy. He was wearing a black tshirt and nice jeans; something a lot of guys wear on dates.

Hahahahaha.

I could tell quickly that the waiter was trying to place me. He clearly thought that we must know each other and was trying to figure out how.

Anyway, I was so embarrassed, and just decided to play along like we knew each other. My date arrived a couple of minutes later (he got a hug too), and we ordered dinner. At the end of the dinner, the waiter dropped off the check and was like, “it was so good to see you again!”

:-)

I’d like to start by saying that I am happily married and have been with my (amazing) husband for 12 years. In the Before Time, I casually dated a guy with ‘born to kill’ tattooed on his throat, who, after dating for a few months, invited me to a fancy dinner in the North End. Turns out he also invited another woman he was dating. He introduced us, we all sat down to eat. I was in a trance for the first half of the meal, until finally I shook myself awake, told him off, and left. I’d like to say I never saw him again but I found out a bit later that our relationship was immortalized on Google street view. Whenever someone looked at my apartment for the next seven years, there we were, standing on my porch.

I often think to myself, will the first dates ever end? I met up with a guy from a dating app. We messaged for 10 days and he seemed totally normal. We went to a small plates restaurant where he ordered one small plate for us to split, the tiniest portion of meat. Who orders that on a first date? He proceeded to share his life story, from being raised in a cult, not knowing how to multiply until 15, to wishing he could quit his job and relax in a hammock while smoking weed all day. Told me he wanted to sell his car to use public transportation…we live in Texas, there is very little public transportation. Wanted to move to Peru, a country he had never visited. Did not even offer to pay for my drink at the bar after I had drove 45 minutes in the rain to the restaurant. The real kicker, he asked me to go to a sex store at the end of the date…I worry for the girl who thinks any of this is normal. I’m learning to be strong and leave when I know things aren’t going well. Dating is hard to navigate, I could really use a manual or a maybe margarita.

My most awkward date started like a fairy tale. I was at a fancy Teen Magazine party in LA and he was the bass player in a semi-famous band they had hired to play. We made eyes at each other the entire night while he was on stage and when they were done playing he made a beeline right to me. We hung out for a short time with his “children of celeb” friends and made a date with me the following morning for brunch. I thought it was so dreamy that he had made a date for a ‘sober’ time, rather than get me to stay at the party all night. I had stars in my eyes when I showed up at the brunch but the actual date ended up being SO boring. The conversation flowed like molasses and at the end he actually TOOK A FEW OF THE DOLLARS I had left for my own tip (we went dutch….eye roll) “Gas money” he said. WOW. The dream is NEVER the reality, my friends.

My most awkward date was a set-up through a friend of a friend. “He’s a great guy! I think he would really like you! He works with troubled youth!” But he also lied for fun. We talked on the phone before we decided to meet in person and he would ask me things like “So, do you have any problem dating someone who is divorced?” When I started to answer he interrupted with “Just kidding, I’m not divorced!” Then he asked if I liked dogs, and pretended to be calling his dog “Come over here, buddy…” But just kidding, he had no dog. It was like an SNL skit. Huge red flags/what the hell was I thinking, I agreed to go on a date with him. He rode his bike to my place, but wouldn’t leave it on the street. He also didn’t want to leave it in my bike room…he wanted to bring it to my apartment. On the 6th floor. But he was afraid of elevators (so am I, but I don’t pull that out on the first date). So he carried it up 6 flights of stairs. We went to a street fest where we ran into an old friend of his, and he lied and told the guy we had had been dating for 2 years. But he never corrected that one with a “just kidding”. The conversation was horrible. He said, “I hate small talk…why don’t you ask me what I think about abortion?” And we still had to go back to my apartment to get his bike. (Such a bad decision on my part to let him put it in my apt.) Worst date ever.

I married the man who turned what could have been a non-date or bad date into one of the best dates of my life. I had been to the physical therapist in the morning and had a terrible, raging dizzy, spinning spell. The PT sent me to an ENT who recommended an inner ear exercise (to reset the tiny bones in my inner ear). I planned to cancel my date that night. I was feeling so terrified that I might have another dizzy spell and I was definitely not feeling myself. When I tried to cancel, he said, “Let me call you right back.” When he called back, he offered to take me to my ENT appointment. He had educated himself about the inner ear and had some thoughtful questions for the ENT. He held my hand while the ENT tilted my head back to induce a dizzy spell. I was myself. This was me – full of fear! My date stayed. He saw the raw fear, he watched and learned how to do the inner ear reset. He took the info sheet from the ENT and promised to help me do the reset, every hour throughout the day. He invited me to reconsider our dinner date. “I think you can still do it,” he said. He knew how much I wanted to eat at this special place. I had made reservations months in advance. So, we decided to try it. He packed blankets in the trunk and set the timer on his phone. Every hour, he was by my side, holding onto me, talking me through the spinning that ensued from the reset exercise (with me on my hands and knees). Next the the road, in a parking lot, behind the restaurant, on a patch of grass… I clung to him, whimpering at times, until the spinning subsided. Between the hourly reset exercises, we carried on with our date. We had amazing conversation, fabulous food, and lots of laughter. I was completely shocked at how kind, helpful, understanding, and calm he was. My fearful reactions to dizzy spells did not scare him away. I felt genuinely seen and cared about. He had seen me at my worst, and he did not run away. We’ve been married for almost 3 years now, and he is absolutely the VERY best!! My dream come true.

I had a mix up like this with a Brian from work, who I thought was Ryan from school when he called. Needless to say, it was very awkward when I figured out the mix up, and even more so when he took me by his church on the way home after dinner and made a not-too-subtle joke about asking if I would be interested in learning more about his faith. (I wasn’t.)

Awkward date! Got to chatting with a guy on the bus and we made a date for the next weekend. I didn’t think it would be amazing but he seemed charming, and I was curious. He is enthusiastic, sending multiple texts (“I can’t wait for our date, can’t wait to see you”, etc.)
Cut to:
He suggests a Marina district karaoke bar that runs bad homemade commercials on TV. I counter with a bar on Polk Street (the Hemlock, RIP).
We meet up. At the bar he implies that we’re slumming it, tells me he thinks Trump will win the election because his “generals are all such smart guys” (this is pre-election, obviously!), and talks about his love of first person shooter video games. His primary interests are playing video games with his roommate and getting food delivery. The conversation is stilted. Loooong silences. He does not tip the bartender.
After half a drink I know this isn’t going anywhere good. Still, the night is young, and so are we.
We get dinner (he pays, and I did not have any qualms about letting him do so) and then head home. He gets out at his bus stop, I get out of mine. He keeps texting/calling for a week even though I tell him honestly that I’m not interested in seeing him again.
A few weeks later, he hits on a friend of mine who is basically my doppelganger, and then tries to pick her up a second time shortly thereafter.
Fred, if you are out there, you make a good story…

He waved to me from across the empty college cafeteria. He was cute. Amused, I waved back. He joined me at my table and started talking. I thought, “How funny, he thinks I’m my twin.” (It happened all the time.) He walked with me to class and outside my building said, “I’d like your number. We could go out?” Because in those days I was unable to say no to someone to their face, I handed it to him, but laughing, said, “You can have it, but I’m not who you think I am.” He looked confused. (That always happened, too, following this statement.) “I’m not Em. She’s my twin,” I said. He said, “You have a twin?” A feeling of horror expanded from the pit of my stomach. In addition to cute (from a distance), he had been strange.

And that the “meet cute” that quickly unraveled into one of the most awkward and awful dates of my life. It was the age of landlines. The time when you couldn’t text your sister, “Do you know a cute but slightly creepy guy who wants to be a paleontologist?” But also the time when you could choose not to answer the phone and (without caller ID) not know who you had “missed.” Ha.

hahaha that is so funny.

Mine was a series of dates. With the same person. I was young – 19ish – and yet, 30 plus years later I still have a hard time saying NO to someone I have NO interest in because I imagine how hard it is to put yourself out there and ask someone out! (oh and I might have initially said yes because he had a cabriolet convertible and I wanted to ride in it haha).

So…he was my stepfather’s (very nice man) cousin. And he worked with my sister at the ambulance. Plus, I worked with his Uncle who was a super cool guy so I thought he must be cool. I was walking through the parking lot at my work (a grocery store, I was in high school) and he drove past me. I was said hi and he slowed down and was talking to me. I made fun of him for having little crossed golf clubs on the sides of his car with his initials (so preppy and ridiculous!). He laughed and said I was cute and asked me out for dinner. I said sure.

He arrived in his volvo. WHAT!???? No one wants to ride in a volvo for a date esp in the late 1980s when they were super uncomfortable. He got upset because I didn’t sit in the car and wait for him to open my door and I opened the door at the restaurant. We went to a trendy restaurant in Chestnut Hill (a very hip place outside Philly) AND THEN he proceeded to tell me about the long time girlfriend and their relationship and how he thought they would get married AND then he started to talk about his dead father AND THEN he started CRYING.

Remember HIP restaurant – so the tables were like inches from each other. And everyone was looking at me like I did something. And he’s saying “I feel so comfortable with you, I never talk to anyone about all these things or cry like this!” and I’m thinking “OMG stop crying…I don’t know what to say…I hate being here” so then he takes me home. at that time I had a cat who would run up to me whenever I got home.

He didn’t like cats (another strike against him added to the volvo AND the crying AND that he was a black republican which in my 19ish year old brain was a total oxymoron) so the cat runs up, I pick her up and he backs away THANK GOD because I was sure he was going to kiss me.

And then (to my still utter shame and embarrasment) I agreed to AT LEAST two more dates. One we went to a jazz ensemble (my least favorite music at that time) at a hotel down in Philly…again, I was like 19…so this wasn’t fun for me. oh let me sit here listening to this music and drinking a shirley temple. yay! and praying the whole time he won’t start crying again. AND we drove in the volvo again!

the last time I was like “you know I really want to ride in your convertible” so he was like “ok we can go out for ice cream” I was like ok, can I bring my little sister? (she was 14ish) he agreed. ON THE WAY THERE they got into an argument about politics. And he literally said, “women shouldn’t discuss politics.”

I was like UM WHAT? and he went on about how we shouldn’t stress our brains etc. THEN we got to the ice cream place and he sits so he can watch his car. AND THEN a group of kids walk by his car and they are looking at it…(because it was cool back in the 80s) and he gets up to go out and tell them to NOT TOUCH HIS CAR and MOVE ALONG. My sister is FURIOUS about the women and politics thing PLUS we were not republicans and would never agree with almost any of their policies.

Each time we got home the cat would run up and one time he was all “aren’t you going to let me kiss you” and I was all “oh haha probably not.” so awkward.

I finally went back to college so didn’t have to say yes or no anymore and then I just wasn’t home when he called. He got back with his old girlfriend, they got divorced, and he’s currently single. why do I know this? Because my MOTHER still thinks we might get together and says he asks about me all the time and my sister (older one that he was working with) is still friends with him on facebook. gah…

OH MY GOSH! My mom recently told me this story, which I don’t remember so I must have blocked it from my memory, I am not even kidding! When I was a senior in college I worked at my local Abercrombie & Fitch and this guy that worked there was kinda nerdy and quiet and from one of the more rural areas nearby. He asked me out to dinner and I always had a hard time saying no to people’s faces about first dates, so I said yes…. I met him at dinner only to find his entire family there and he introduced me as the girl he was going to marry. SO AWKWARD. My mom said I called her the next day to tell her all about it and how horrified I was. I remember how awkward he was but I seriously can’t recall the details so I am glad I called her to tell her about it!!!!

I had online date, we met on chat (ah, that old days :-)) ). While we were chatting he said that he is very handsome, so I expected, I don’t know, somebody like Paul Newman when he was 30 years old. Well, reality :-)). When I saw him, the first sentence which pooped from my mouth was: ” You’re handsome only to your mother!”.
I was really disapointed :-)).