Nostalgia: Some of my all Time Worst Dates

I got married a little less than a year ago to a marvelous gentleman. He really is the greatest person in the world for me. Since we will go on “dates” for the rest of our lives, it’s a given that some will be better than others. Some fail miserably, but at least it’s sort of funny and we are contractually obligated to move past it.

Recently we were seated smack next to an ex-girlfriend of his at a restaurant. (Why is LA so small?) I sat rigidly facing ahead, unable to turn around or even move because my staring problem would certainly flare up. He awkwardly shifted his position to hide behind my head. We are mature adults after all. This went on for a while until she and her party finally left. I still don’t think she saw us. It’s too bad because I was looking f-i-n-e fine with my Something About Mary post-scrub cap bangs and flannel-avec-heels slapdash ensemble.  Anyhow, what could have been technically a bad date was still great. It was actually quite funny, and it got me to thinking with fond nostalgia of my all time worst dates, of which there have been quite a few…

1. My ultimate worst:

I went for sushi with a guy I met in a Whole Foods. I let my friend talk me into it because she said it was a “cute meet” and that he looked like an “Asian Keanu Reeves”. I met him for dinner after a long day in the OR, pretty famished – famished as in I had eaten nothing since breakfast and I’d been up since 5am. As the hostess began to lead us to our table, he proceeded to demand a window table and said we would wait 45 minutes until one was available. I insisted that seeing food was much more important to me than seeing water and so we were seated. Things he actually said:

“So, how did you change inside when you cut a person for the first time?”
“What does it feel like to cut a person?”
“Wow. You eat and drink more than I do.”

Check, please. Take me home – I get up at 5am. I’ve never been so glad for that excuse. Needless to say, I failed to return future calls. He then sent me a package of Fresh bath products and a letter saying how “disappointed” he was in me and my failure to recognize a wonderful man. You see, he thought I was “smart”.

The story continued a couple years later when a woman giving me a facial was talking about a breakup and I recognized the guy she was ranting about to be this very guy! Apparently he had like 5 girlfriends. And herpes. Sometimes we dodge big bullets, ladies.

2. Snooze Fest. Literally:

I went out with a guy from He was a “lawyer” but in real life he turned out to be a law student. That’s fine, but he wanted to go to dinner at 5pm and then talked about law school non-stop. I’m sure this was really interesting, but I was post call and… I actually don’t remember any of it. I only remember hearing him say: “Are you okay? Do you want to go home?” I had fallen asleep at the table.

3. I love you:

In college, I agreed to go on a date with this guy who asked me out for a Friday. Lo and behold, that Friday was Valentines Day. Ew. One could have easily coasted past this slight first date faux-pas, but not him. He brought me a balloon that read: “I love you”. Of all the balloons out there, he chose this one. Several dates later, when I was breaking things off, he actually said he loved me. One reason? We had so many things in common- “We both like sushi”.

4. Are you even trying?:

I went to dinner with a really super hot tennis instructor who was really charming every time he came into the bar where I worked. However, come our date, it was like pulling teeth to get him to talk. I must have been thinking that, because I remember asking him if he had any fillings. I asked his favorite color. I asked his favorite cereal. I was that hard up for a conversation. Crickets.

5. Radioheadache:

There was a cute bartender who I decided to go out with because he liked Radiohead. Let this be a lesson: Liking Radiohead should not be your sole selection criterion for a potential gentleman friend. When we were out, four different people approached me, warning me to be careful because the guy had been through anger management rehabilitation programs roughly 5 times. Apparently Thom Yorke hasn’t helped him in that respect.

6. Repeat offender:

A very handsome guy I knew through work wanted to take me to dinner. We had known each other for a while and I am pretty sure he knew that I don’t do red meat. So where did we go? Ruth’s Chris Steak House. I reminded him of my eating habits but enjoyed something there nonetheless. Whatever. It turned out he was a real jerk (I won’t go into details) and I refused to go out with him anymore.  Eventually he conned me into a second chance by offering making me dinner. He was very charming, you see.

What did he bring to make? Steak. Sigh.

Every now and then, as I sit watching Devil Wears Prada or whatever with my husband, I am struck with profound gratitude that I found him. But I will miss terrible dates for the stories! Hopefully we will have some more bad ones – gotta keep it spicy, after all.

Tell me your bad date stories in the comments below! Laughter cures heartache. Each bad date is propelling you further toward a good one, and making you more of a badass.

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  • Tammi Jean Haynes

    I had a crush on this guy for a long time and finally worked up the nerve to ask him out. He suggested we watch “Wizard People Dear Reader” which is actually perfect for me as a Harry Potter super fan. Date night! I get to his house, he puts on the movie, I sit on the couch, and he SITS ON THE FLOOR! And not near the couch, he’s like 5 feet away. We watch the whole movie like this and at one point his roommate stopped in and ate some pizza. Then he walked me to my car, said bye, no hug, and that was that.

  • Milaka Falk

    A friend of mine (who lived out of town) called to tell me that her brother visiting my town for business and asked if I would take him out to dinner. No problem! Come to find out, this was not really an “in town and would like company for dinner”, she had built it up to him as a first date with potential. I caught that vibe immediately. It was VERY uncomfortable. But I was getting a lot of mixed signals. At dinner, when our waitress left to get our drinks, his eyes followed her for a few long seconds and then he turned to me and said, “Wow. I’d f**k her!” Then he proceeded to go back to trying to woo me! Ick! He actually seemed surprised that I dropped him off at the hotel lobby!

  • Winly Mallard

    Thank God I didn’t have bad dates, except one, when I was in highschool! And a procedure was in place so that consequence couldn’t occur(smooth for everyone for sure). One other time as an adult, it wasn’t a date at all for real, it was a business arrangement where I allowed and trusted a certain person to be my driver, said person was put in check by higher authority within “as stated” company, and I did not have to fully employ certain procedures, or suffer the full on consequences that could of occurred, that’s called: “A back up plan”. Also two other ocasions when I allowed someone else to be my driver, I could of done without, especially one, by far. And these people are well aware of who they are. I have not done such behaviors ever to anyone when I was the driver. A third in the non highschool category, is also to be reconized this year. He lies though. Just saying. TRUE TRUE TRUE TRUE. TRUTH & REALITY IS LOVELY WONDERFUL TO ME.

    • Jenn Brown

      After several months of dating someone who I knew was TERRIBLE at planning, I relented and let him take the wheel. He wanted to go see a concert in Atlantic City (a 3-hour drive from where we lived). The morning of the show, both of us woke up with itchy, red eyes. Neither of us really knew what this meant, nor were we smart enough to call a doctor. So we headed out, our eyes progressively getting worse. He drove, swerving while putting Visine drops in every 10 minutes or so. We went through an entire box of tissues removing discharge from our eyes, and he eventually called a nurse friend of his who told us we had pink eye (duh). When we made it to Atlantic City, we were starving, half blind, and grumpy. After walking around in circles for what seemed like hours, he finally admits he had not made any reservations for dinner ON A SATURDAY NIGHT…AT THE BORGATA. Needless to say, we couldn’t find a place with an open table or a wait that would get us food before the concert, so we sat in the casino area, played a few slot machines, and waited for the concert…with our puffy eyes oozing bacteria. It was super sexy. I drank vodka tonics for the rest of the night and spent the whole concert drunk and crying because I was hungry, worn out, annoyed, and out of tissues. I don’t know why I assumed we would end up at a hotel after a late show 3 hours away from home, but it turns out he hadn’t reserved a place for us to stay either. We drove around (in circles of course) for an hour trying to find a room, then he stopped at a gas station where I totally assumed he was getting me a sandwich, but returned, inexplicably, with cough drops and gummy worms. This is the moment where I stopped speaking to him for good, but it also meant that I had to keep my angry, angry mouth shut when he pulled into a rest stop, parked the car, reclined his seat, and went to sleep…in a parking lot, in New Jersey, in February, with pink eye, without sandwiches. Oh…and did I mention it was Valentine’s Day? No big deal.

  • Catherine Paige Maier

    This reminds me of an episode of Parks and Recreation. Amy Pohler plays a character who is nervous for a first date and goes through snippets of former “first dates”. One quote goes something like this, “One time I went to the movies with a guy and I fell asleep… I literally woke up with his hand in my mouth!” Every time I watch the episode I lose it with laughter.

    • Paula Gonzalez

      Here’s a link with that exact monologue from Parks and Rec! Amy Poehler is a comedic genius. This episode is one of my all-time favorites!

  • Sara Read

    This isn’t actually a story of one of my dating nightmares, but instead it’s one my poor mother had to suffer through. One day when she was a super poor college student a man of average handsomeness asked her out. She agreed despite the fact that she wasn’t really interested because she figured she’d get a free meal out of it (nice, mom). So he picked her up and they went out for dinner and then the main event that was the “surprise” he’d been promising her she’d love all throughout dinner: they were going bird watching. I mean really, does it get more romantic? My mom spent the next three hours traversing the woods where she got scrapes and ticks. Needless to say there were no future dates and that oblivious boy is still probably single.

  • Alexandra Anderson Conrad

    @Catherine “Skywriting isn’t always positive” . Love me some Parks and Rec.

  • Coral Denisse Emmanuelli Costas

    mine isn’t exactly a first date thing. I only went out with this guy once, to the movies, with an entire group of his friends. We also took the same class together at college and had to do an oral report together. I think I even visited his church once, with my mom. But first date? Nope, none of that. Still, one day he came over to my house unexpectedly to watch a movie. I accepted, watched the movie and then used the typicall excuse, “It’s late and tomorrow I have to wake up suuuper early.” He agreed and left. Not before giving me this awckward hug where he’s all into it and i’m trying to keep my body as far away from his as I can. I thought, “ok, now it’s over, but then a few hours later I got this creepy email asking me if I was “hot”. Not physically hot. Not sweaty hot. But horny hot. EEEEEWWWWW!!! I immediately ignored him from then on and he eventually dissapeared, but not before leaving me an eeeeextra long and wimpy voicemail asking what had gone wrong and how we had such a strong connection.

  • Kelly Crafton

    This was more of a ‘double date’-ish… my friend and I invited two guys to a movie. Trying to put ourselves out there and all that. It went ok-ish. The guys said we should go hang out elsewhere after the movie. We said ok… however we soon thought better of it. By the time we got to the parking garage we were seriously considering ditching these guys. They were both being awkward (particularly my friend’s ‘date’ during the movie). We ended up deciding to be nice and join them inside. Once inside, the conversation was terrible. The guys had sat so my friend and I couldn’t sit together (and thus help each other out during this awful evening) AND my friend’s ‘date’ kept turning and blocking me off from her so I couldn’t even talk to her! And she felt pinned in her chair by this as well. So the guy I’m sitting with during this proceeds to tell me first about how he hates cops… oh hey, my mom is a cop. You really wanna go there? Then he goes on to tell me about how every cat he has owned DIED. And let me tell you, they weren’t from natural causes! Not a good story for this animal lover and particularly cat lover! Ugh, needless to say I stopped answering his texts etc after that.

  • Shaziya Niamh

    God I’ve had some terrible first dates. There was the guy with the teeth, the one who told me how he had embalmed his own mother (she was dead obviously), the one where we made mix tapes for each other but conversation just wasn’t happening, the one who I left halfway through and got drunk with my friends as he was so boring. My very first date where I was taken to burger king (its not where dreams come true) and many more. I could go on but I’ll save for another occasion

  • Lauren Lisbeth Miller

    Well this wasn’t really a date but while I was in college I went to a party with an old friend I hadn’t seen in a few years. The whole night he kept putting his hand on my lower back and being super creepy, so I proceeded to fetch drinks often to dodge his presence as I knew absolutely no one at this event. By the end of the night I was a bit boozed and asked him to take me home. While in the car he leaned in to kiss me and I ducked and then kissed his hand ( I have no clue why I thought this was a good solution) Anyway it was so awkward I had him stop halfway home and called a friend to pick me up.

  • Rosa Parx

    worst date ever was actually a blind date. my friend from work set me up with a guy worked as a radio DJ for the local pop station and also was a volunteer fireman, so I thought okay, there might be some potential. Wrongo! He showed up late, he had a mullett, he was wearing big white tennis shoes and acid wash jeans and a big ol gold chain. he took me to Applebees and throughout dinner, he was basically watching the TV behind and above my head b/c Nascar was on. then towards the end of dinner he says “hey, sorry if you think I’m not interested in what you’re saying and I keep looking away…It’s not that…I have a glass eye. I can take it out of you want to see it.” I had no words. To this day I still refer to that night as my “half blind date.”

  • Stephanie C. Rogers

    This isn’t a first date story, rather a terrible pick-up line adventure…A guy once handed me his number along w/the words, “But don’t call me ’til tonight, ’cause I have dialysis at noon.” Bless his heart…and kidneys.

  • Kellie Taylor

    I had gone to Chicago to visit my boyfriend for new years and I was really hoping that week he would propose. So he takes me all around chicago and all we do is walk everywhere, which was fine i love that city. He then suggests we get something to eat at Grand Lux Cafe, i was soooo excited. So we get the restaurant and order our meal, my serving of pasta was huge and i could only eat 1/4 of it so i let my boyfriend eat the rest. During the meal he calls my mom, with me there, and asks her if he can marry me, lame but still whatever. After we’re done eating he asks me to pay for my meal because it was too expensive. So i paid the $20 dollars for my meal. Then we go to watch fireworks for the new year and he pulls out the ring and said will you marry me, no down on his knee or anything so anti climatic. i said yes but 6 months later he turned out to be a total creep and abusive so needless to say i got outta that real fast. dont marry a guy who makes you pay for dinners that he ate…haha.

  • Amy Lyles Toland

    A friend and I went on our first date to see Titanic. First of all, he cried like a baby through the whole movie. Serious sobbing- I wasn’t even crying. Later during the movie he asked if I had any ice left in my drink. I said sure and handed it over. He proceeded to wash his hands and face with it. Little did I know- until we left the theatre, he was covered in blood!!! He had a nose bleed and instead of excusing himself to the restroom to clean up used ice and his shirt. This was the most awkward date ever!!! I did give him a second chance. He took me to a coffee shop to look at his baby pi tures. Seriously! No more dates after that.

  • Oka Tai-Lee

    On a first date with someone I met on a dating site — the first words out of his mouth, after he had already arrived 20 minutes late and was not in anyway apologetic about it, were “WOW, you look so much better in your photos”. Then he asked me if I had borrowed the Cat in the Hat’s gloves (I was wearing red and white striped fingerless gloves – it was cold and around the holidays and they are cute no matter what!). And if that wasn’t enough, he told me that sometimes if he went on a bad internet date that he would go onto the website and find the person with the highest “enemy” percentage and try and convince that person to come over and have sex with him. Needless to say, I fled very quickly and put “DO NOT ANSWER” next to his name in my phone.

  • Caity Johnson

    i went on a date with a guy from a dating site that was so unbelievably awkward. we were supposed to meet for coffee after work, but when we got there, the coffee shop was closing, so we went to a little restaurant/bar just down the street instead. once seated i ordered a cocktail and he ordered a soda. getting him to talk in a voice louder than a whisper was like pulling teeth, and he kept excusing himself from the table every 5-10 minutes. finally after the fourth time he had left the table, he came back and apologized that he had to keep getting up, but that he was sweating excessively because “he got really nervous around pretty girls”. Needless to say, I got the hell out of there as fast as I could and didn’t hear from him again.

  • Jacqueline Kate Barlow

    I was staying in a youth hostel in a new city trying to decide if I wanted to live there. So one day I’m just having my lunch and this young man, who claims to be living there while his new apartment is refurbished, comes in and strikes up a conversation. He seems perfectly sociable, despite the fact that he has only one hand — the other arm ends mid-forearm. He asks if I know the city well, I say not that well, he offers to take me on a tour of the area. He takes me on a tour, after it’s over we grab a beer, and afterwards walk back to the hostel. We get to his room. He is looking at me intensely. He says, “I had a really good time. Did you have a good time?” I say yes, even though he is making me extremely uncomfortable. “I had a good time too,” he says, then leans in and kisses me with astonishing ferocity, especially considering the fact I do not open my lips or even pucker. It was like being mouth raped. Incredibly, I feel the need to MAKE AN EXCUSE instead of just running away. Luckily, I don’t think I saw him after that. I ended up living in that city for a while, though.

  • Melissa Childers

    This guy would ask me out everytime we ran into one another around campus. We had a lot of common friends, but I did really think we had much in common. This went on for a year until I said “sure, why not.” We met at a local park for a picnic, but he didn’t bring any food. We sat in the park for awhile until he suggested that his parents lived close and we could go grab something to eat. When we got there, he introduced me to his mother. He then asked her to make us a microwave pizza. I sat in his mom’s kitchen and shared a “pizza for one.” Then we went to the family room and watched tv. At one point he looked at me from across the couch, and asked if I wanted to make out. After watching tv for another 30 minutes, I made an excuse to go home. On the way back to the park to get my car, we stopped at a gas station so he could drop his last 8 cents into the gas tank. Now, I’ve been on plenty of free dates. Some were great. This was just a nightmare.

  • Crystal Olson

    A friend I used to work with asked me to meet him for drinks and catch up. So I meet him at this super crappy restaraunt and we have a good time even though the food was terrible. Then he invites me back to his place to watch a movie. I was totally oblivious to the fact that he thought it was a date!! I spent the next 2 hours sitting stick straight on the edge of my seat. Hands on my knees staring straight ahead while he alternatly rubbed my back and brushed his fingers across my neck! I Felt so bad! I didn’t want to say anything because I really liked him and I didn’t want to make him uncomfortable. Thank God he didn’t make any serious moves. As soon as the movie ended I jumped up and ran out

  • Joseph Van Alstyne

    I haven’t had any incredibly noteworthy bad dates, but one stands out in particular…

    This guy added me on Myspace (that should have been the first clue…), but I saw that we had a close mutual friend, and hey, it was high school. Didn’t know any better. We end up chatting and actually hit it off pretty well. But then we arranged a date to go see a romcom. We meet at the theater, hug, sit down, and watch the movie. The only thing we say to each other the entire time is “Hi.” During the movie he tries to hold my hand, and I let him. But then we walked out to his car, and he tried to kiss me. We exchanged like five words the entire date! I ran to my car afterwards and got the hell out of there. Never talked to him again, obvs.

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