Nostalgia: Some of my all Time Worst DatesAlexandra

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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  • Brookeand Mckenzie

    Love this, we have many similar posts!

  • 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.

  • Alexandra

    Um, we could make the most awesome horror comedy book about first dates! Good stuff here! Keep me posted, since I don’t get any more first dates :( Maybe I can try to ruin our dates though, just for giggles…

  • Chloe Annalisse Stamper

    Once I went on a date with an older guy, who seemed interesting and charming initially. He drove a few towns over just to meet up with me. The date started well, we had a nice picnic in the park by the lake. After the picnic we started walking along the path near the shore, and I spotted a seagull in dire straits, like truly, this creature was on its way out of the world. I am a professional animal lover, and couldn’t stand to see this awful display of seagull misery, so I suggested we move it to the soft sanctuary of a nearby patch of foliage. His solution, however, was much different. He picked up a stick and marched purposefully toward the creature. He then proceeded to hit it with the stick, as a small crowd of an elderly couple and a woman with a toddler and myself looked on in shock and horror. He was ineffective in his death stick wielding, so the bird was just making these awful noises between swings and thuds.
    Eventually he succeeded, dropped the stick, and walked back to me like nothing out of the ordinary had happened. I was so shocked, I didn’t know how to proceed… So we ended up walking around town and going to a used furniture store, and then it started hailing, so I went back to my apartment, where he tried to kiss me. My roommate conspired with me and eventually we were able to get rid of him (I think I made up some excuse that I had something to do). He was shocked when I turned my head when he tried to kiss me, and continued to contact me. I blocked him from everything and ignored his calls.

    That date takes the cake for me, but there was another in high school where I went to see Cloverfield with a boy I’d been dating for a few months. I get motion sickness and I get scared easily. I threw up twice and cried. He later broke up with me on prom night.

  • Charles Constantine

    Don’t we all have bad dates and good dates? Is it quite possible that some of these men went home and said to their friends, “Oh my god, she just wouldn’t stop complaining.” I am pretty sure the point of dating is to search for compatibility. Try remembering the good rather than the bad and your next date might go a little bit better, even if the two of you are not compatible.

  • Kimberly Hawkins

    I met this guy through eHarmony (ugh…eHarmony). He lived in South Dakota. I’m not one for LDR’s but, I thought “What the heck”. We really hit it off online and over the phone, I really liked him. He was going to be in town for a conference, so we decided it would probably be the best opportunity for a first date. He came with a group so he didn’t have a car. I agreed to drive. When I met him, he looked way worse than any of his pictures. He was wearing a baseball hat, a t-shirt, and nice wool dress pants and these really goofy looking shoes. At that point, I wanted it to be over. I wanted to pretend I didn’t see him but, my stupid hand was already waving at him. We went to dinner…a nice dinner that I paid for. He kept asking me “Do you not make eye contact with people when you are nervous?”…umm, yeah, that’s it. Then I had to drive him back to his hotel, which was 2 hours away. While I was driving he began to snuggle with me and nuzzle my neck. I prayed there weren’t any police out because I was doing 90…I just wanted it to be over. When we finally got to the hotel he was staying at I was sooo afraid he was gonna try and kiss me that I punched him the arm and said “I had a great time friend, I’ll call you soon” and got back in the car and left immediately.

  • Vanessa Maria Loaiza

    On a first date, a guy told me in response to something I can’t remember, “oh that reminds me of a book I want to write, about how the downfall of western society was the women’s movement.”

    Yeah, not the best thing to say to an academic let alone a woman at all. The sad thing is that instead of seeing why he was wrong, he probably dismissed me as a man-hater. For fun, I emailed him the next day with a meta-analysis about how maternal care is just as good as non-maternal (i.e. day care) care for children (the opposite conclusion being one of his groundless talking points). Never heard from him again. I have soooo many more but that’s the most recent bad one.

  • Abbie Anderson

    ON A FIRST DATE…I had a guy offer to make me a didgeridoo out of PVC pipe because it was a hobby of his. He said he treated the PVC so that it looked really authentic and said that they sounded amazing. He’d only made like two, one for himself and one for his mother. I politely said that I probably wouldn’t be needing one and that he should use his talent and resources to make them for people who were more passionate about the music of the didgeridoo. Then he proceeded to YELL at me for being ungrateful and try to convince me that I would really like it…all while YELLING. I texted my friends my location and then fake ran into them and left him at dinner, still angry about the fact that I didn’t want one of his hand crafted instruments.

  • 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.

  • 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

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.”

  • 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.

  • 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

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