Dating Disasters

Last year I had so much fun writing this article, I thought it would be fun to bring it back. As an ode to Valentine’s Day, I figured it is only appropriate to share some extremely painful yet hilarious dating stories. Because honestly, what better way to celebrate this holiday than with a good hearty laugh. Without further delay, here are some brave women who made it through some really horrible dates.

As we all know, there are a variety of factors that contribute to a bad date…

Let’s start with the men with a second agenda:

It was our 3rd date and he invited me over to his place to watch a movie.  Then he burst out with a story regarding toothbrush head replacements, asking if I used the sonic electronic toothbrush. I said yes, and he asked “oh, well I accidentally got the wrong model.  Do you want these?”  And right before I answered “sure, if you don’t need them” he interrupts with, “I’ll sell them to you.” My jaw dropped. I never saw him again after that.

– Anonymous lady who had too much sense (or cents).

I agreed to meet this guy for a coffee date at Starbucks. Of course he chooses the one Starbucks located on Canal street. Canal street? You go buy knock-off purses on Canal street not to get coffee. That should have been a sign to cancel, but I went. It turned out that specific Starbucks actually ended up being closed due to plumbing problems. So we tried again and eventually met in a Starbucks around Union Sq. I kid you not, once we met and sat down he takes off his shirt and tries to sell me Facebook add-ons! He had his whole business plan and everything. Uh-uh, I’m done.

-Anonymous lady who’s now happily sipping Starbucks in peace

There is always the Ex factor:

I had been looking forward to going on a date with …. let’s call him James,  for awhile.  He was the first guy in some time that I didn’t meet through or tinder. It was exciting, we had been texting all week! The conversations were going great, then the big day finally arrived….. he called about 2 hours before our date saying he had to cancel because his ex-girlfriend just told him she was pregnant… needless to say, the date never happened!

– Leonor Robels from Red Soles and Stilletos

All you need to know is that we got into bed and he could not, for the life of him, get it up.  The rest of the night turned into him crying for 4-5 hours while talking about how he just broke up with his ex. Once he was asleep, I decided that was my chance to escape. So I ran out in the middle of the night. Classy, I know.

– Anonymous girl who ran away.

I was in the airport having just gotten back from Morocco when I saw this lady who had the most beautiful coat on. I asked her where she got it and started chatting. I needed something to get my mind off of the vacation that had gone so horribly wrong. I mean horribly wrong, where my date ended up in the hospital. I figured I might as well talk to someone with half decent taste. A few minutes later my date, who is now in a wheelchair, comes rolling over. Turns out the women I have been chatting with was his Wife! Just when I didn’t think things could get worse, I ended up sharing a ride with them both from the airport.

– Lynn H.

The ones who think a few drinks will help:

My fave was a guy I met on plenty of fish. He was so cute. We agreed to meet for drinks, but he said he had to take a train to meet up because he had a breathalyzer hooked up to his car. That was a huge red flag. So of course on our date he got so wasted that he fell out of his bar stool and fell asleep on the bar floor. The bar staff literally had to drag him outside and put him on a park bench in front of the train station. Best part was when he woke up on the bench hours later, he kept trying to facetime me. Not call, but facetime. 

-Melissa R.

I went over to this guy’s place who I’ve been dating. It was super late because of my ridiculous work hours. When I arrived, he was already drunk, sick and congested. He said he wanted to take a shower to clear out his sinuses, so I just went to sleep. Couple hours later I woke up and I heard the shower still running. He decided to fall asleep in the shower. 

-Anonymous lady who’s no longer babysitting drunks.

Then there are the guys who leave you speechless:

I went on a date with this seemingly conservative man. It was a nice dinner at very plan restaurant. At the time, the dating book “The Rules” was super popular, so I knew I wouldn’t hear from him for three days. Like clockwork, on the third day he contacted me saying he had a great time and would love to see me again once he gets back from skiing in Vermont. I said no problem, call me when you get back, have fun. He quickly replied back with, “I bet you didn’t think exotic male dancers liked to ski… By the way I am a male dancer.” I didn’t know how to respond but with “ok”.

– Ellese Launer from Rock.Paper.Glam.

It was my second date after completing a fairly decent first date. My head was filled with visions of merriment and comparability. I entered the bar and found my tall hunched over and fidgety date…Not necessarily what I remembered. He chose two seats near the bathroom, and I went to buy my own beer. I sat drinking steadily while he went on talking about himself, and how knowledgeable he was. At one point his head was so slouched over, I am pretty sure he was talking to my crotch. The date concluded with him asking me “So are you going to make out with me now, or what?”… That would be a no.

– Meaghan Lass from Bitches ain’t shit. and other anecdotes (read the full story)

And of course, there are the MIA men:

I had been dating a guy for a few weeks. We were texting throughout the week and were hanging out every weekend.  A week before Valentine’s Day he told me that he was planning a surprise for me and he would call once he  figured out the details!  Well, Valentine’s Day came and went- no word.  While I was sitting at my sorority house irritated the following Monday, I aimlessly perused  Facebook when something caught my eye.  Lo and behold, my MIA date was in a brand spanking new relationship… with a mutual friend of ours.  Needless to say I haven’t talked to him since!

-Sophia L.

The one Valentine’s Day I actually had a boyfriend was in college,
but we couldn’t even celebrate because there was a huge snow storm! So I
ended up eating white pizza and drinking wine with my roomies. I got to tell you, I’ll never forget how good that pizza was though.

– Ashley B.

But every once in awhile you’ll land a good one:

I was on a third date with a guy. He took me out to dinner and soon into our meal, he bit into a pepperchini and it shot juice across the table into my eye. He just started laughing while I teared up and rubbed my eye frantically. He then said “well, at least this wasn’t our first date, or I would have just put money on the table for you to take a cab and walked out, because there’s no recovering from that.” I married this man five years later.

– Kelli G.

I hope you enjoy!

Originally posted on Feb 14, 2015


  1. That was some great post! 🙂 My third date with a gorgeous guy, seriously, I got a bit frightened, cause he was to handsome and hot! He asked me if I can come to his apartment and pick him up and meet his roommates (I guessed he wanted to introduce). I came, those guys were great, everything fine. They were making jokes about his cosmetic rituals and his obsession with beauty. I went to his toilet – dear God! That guy had issues! Never-ever have I seen a girl with such a collection. Jars and bottles of cosmetics everywhere! Later that evening, he opened a lot and started to talk about hair care and facial masks and I was bored to death. Narcissus himself.
    He was very persistent in calling me, trying to figure out what went wrong, how could I not answer back someone like HIM.

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