With online dating as ubiquitous as it is (nine out of 10 single Americans are online!), more people are dating via the Internet than ever before. Sunday was Valentine’s Day and leading up to it, we shared some super sweet stories from couples who met each other online. Sadly, not every online date ends in a happily ever after — in fact, some end in, “see you never” and we have some truly awful first (and last) date stories for you. Thankfully, V-Day is behind us, because these stories might make it hard to feel romantic. Either way, be glad it didn’t happen to you.

Meredith, PR Account Manager, The League

“This date was my first and last date on The League. I had used the app for months but never found anyone interesting until this guy. He was attractive and fit my list of wants (e.g. employed, lives in the city, looked cool/interesting). I was out at happy hour with girls from work when he texted asking if I wanted to get a drink. I had nothing to do that night so why not, I thought.

We met at Pier 73 for a drink. I introduced myself and we started small talk about our days. I barely told him about mine and he started going off. He was so grumpy and aggro as he told me about the terrible day he was having, how he’s sick of SF, how no one here is interested in being creative so he’s hoping to move to Portland or New York or LA, somewhere with real creative minds, etc. I sat mostly in silence, minus the questions I prompted him with to look engaged but it was so hard to pay attention. Here he was on a first date telling me how he hated the city I live in, the culture that surrounds me, the tech industry which I’m heavily involved in, etc. It was painful.

We finished our drinks and he went to the bathroom. I considered just walking out but didn’t want to be rude so I waited. When he came back he had new drinks in hand. Oh great, I thought. Another round with Mister Wonderful. But when he came back, he was a completely different person. He started finally asking me questions for once and when I told him I do PR for consumer and tech companies, he changed his tune. Now all of a sudden he knew everyone in the industry, his dad is super well connected, he used to date Peter Thiel’s assistant (and went on about that relationship for a while) knows this person and that person and goes to the Battery, etc. It was nauseating and so confusing. One minute he hates SF and the next minute he was the typical startup name dropper.

It was getting late and cold, and when I reached into my bag to grab a sweater I realized my keys, which always sit in the same pocket in my purse weren’t there. Damn, I had left them at work — but this was the perfect out. I told him I didn’t have my keys and was very apologetic as I wrapped up and got ready to head out, but he wouldn’t let me leave. Don’t you have a roommate? You can stay with me until she gets home. Want to get another drink while you wait? What’s the rush? No, no, I said — I have a long day tomorrow and need to get home. He wouldn’t stop so I finally told him my office had a doorman that leaves by 9:00 pm so I had to get my keys before then. All right, where’s your office? I’ll walk with you. Damn it again! Now this guy was going to walk with me? Luckily my office is on the cusp of FiDi and SOMA so it was close by, but here’s the kicker — I don’t have a doorman and I didn’t want him to know where I worked.

We walked through FiDi ‘on the way to my office’ and I was desperately scanning for office buildings with lobby/doormen. I remember finding one on Howard and something, and told him, ‘OK, this is me!’ He asked if he should wait and I said no, it’s fine. I might check email and stuff before heading out, thanks for the date, etc. He hugged me by and then waited and watched as I walked inside. I had to legit walk into the building, walk up to the front desk guy and start talking. I pretended like I knew the security guard and made small talk while waiting for him to leave out of the corner of my eye. Once he did, I told the security guy I must be in the wrong building, asked him for directions to my real office (just to not seem so odd) and walked the remaining blocks to get my keys and went home. It was so brutal! He texted me that night to make sure I got in okay which was nice/respectable, but needless to say I never responded to a message from that dude again, and immediately deleted The League that night.”  

 Miles, Assistant Aquatics Manager, Grindr

“After chatting for a while on Grindr this guy asked me out. I wasn’t sure if I was really interested, but thought, ‘What the hell, it’s a free meal.’ We exchanged numbers and continued to chat. The next evening, he picked me up. I wasn’t sure where we were going at the time. After a few minutes of chatting I asked where we were headed. He told me that we were heading to his favorite restaurant. About 10 minutes later we pulled up to Fazoli’s (editor’s note: Fazoli’s is an Italian fast food joint). I laughed and thought he was joking. Nope. We went inside and proceeded to stand in line waiting to order. While in line, he let me know that I could get whatever I wanted. I ordered, we ate in almost silence except for his rave reviews about the endless breadsticks they kept bringing around. He drove me home. I got out of the car as fast as possible.

He continued to text me the following week and I would respond off and on. He asked me out for a drink on a Thursday night, I declined, because I figured his idea of a drink would be a trip to the nearest Casey’s where I could mix vanilla and cherry into whatever pop I wanted. I told him I wasn’t feeling well. I then proceeded to head out with my friends to a thirsty Thursday event at a local bar. After dancing with friends I checked my phone. He had texted me saying that he saw me. I ducked down and hid behind some friends. Got out of there as fast as possible. Needless to say he waited to text me again for about a week.”


KT, Service Coordinator, Tinder

“We had an okay date, had a few drinks, a few tacos. He was nervous and pretty nerdy, not quite my type, but we were having fun. It was a nice night and we were right next to the park (which I go to everyday and know like the back of my hand). So we decided to go for a walk in the park. We got to the ‘beach’ which is a pretty gross sand pit that is filled with stagnant water in the summer. At which point he said, ‘I know this might sound kind of weird, but I think it would be romantic if I could bury you in the sand right now. What do you think?’ I said, no thanks and made my way home shortly thereafter.”

Lana, Fashion Merchandiser, Bumble

“I went to art school for college so I’ve always been super drawn to creative types. I met this guy who was a writer on Bumble and he suggested that we go to Chelsea in Manhattan on a Thursday night when the art galleries have their openings and I was pretty excited because that’s right up my alley for a date.

He’s was tall, cute and had a lot of interesting things to say about the work, so I was pretty attracted to him at first. We went to the pizza parlor around the corner from the galleries for a late dinner and as we were chatting about the starving artist lifestyle and he accused me of selling out for rent money — which at first was in good fun, but he couldn’t let it go. That’s when things got a little awkward. I think at that point we kind of knew that we were no longer hitting it off.

Then, he started talking about how he hadn’t had health insurance in years and he confessed he had a, and I quote verbatim, ‘growth on his groin.’ Um, yeah. Anyhow, after all that talk, the bill came and we split that check because 1) I knew he had no money and 2) there was going to be no second date.”

Penny, Freelance Photographer, Hinge

“In the summer of last year, I decided to finally take the plunge into the world of app dating. I was asked out on a date by a guy on Hinge and he seemed charming enough so agreed to Sunday brunch with him at Farmer Brown. It was one of those rare days in SF where we were having a legit heat wave so I wore white cut off shorts, a tank top and Nike wedges, and rather than take an Uber or Lyft, I decided I’d walk. It was gorgeous out and seemed close enough — big mistake. The walk was lovely and my music was pumping me up, but aggressively walking in the heat not only made me sweat my ass off, but it also made me late. The restaurant was WAY further than I thought and I had to text him that I was running 10-15 minutes behind, strike number one in my mind especially since we had a reservation. When I got to the restaurant, I must have looked like a hot mess. I was “glistening” – my straight hair was starting to get its natural wave from all my sweat, I had beads of sweat dripping down my forehead and my clothes were sticking to my skin. I spent the first half of the date fanning myself with a menu. It was comical at first, I told him what happened and we laughed it off, but it was not the first impression I wanted to make — especially on my first app date ever!

We were seated in the front of the restaurant near the stage but no one was there at the time. SIDE NOTE: Farmer Brown is a soul-food spot with live music on the weekend but neither of us knew this, yet. We got about 15 to 20 minutes into the date and the band came on and started setting up — and that’s where it all went downhill. The music was SO loud, seriously SO loud, that we couldn’t even talk or hear each other — not to mention the guy was singing some soulful, baby-making songs… during Sunday brunch… on my first date… awkward AF. We had to lean over the table to talk to each other and even that was difficult so we spent the remaining part of brunch eating and laughing it off, but totally in silence. We were in such a rush to get out of there that he paid the bill, we left and he drove me home.

It wasn’t a bad date and I was proud of myself for surviving my first blind/app date ever, but serious lessons were learned. A) Do not walk to brunch, ever. Get a car, take the ride to relax and freshen up. B) Don’t go to brunch with a live band or any activity that will making talking impossible — especially if it’s a first date. C) Don’t wear something too casual where you feel underdressed and don’t wear white when it’s super-hot because you’ll sweat right through it.”

*Some names changed to prevent total mortification.

Do you have an online dating horror story you’d like to share? Tweet us @BritandCo!

(Featured image via Marisa Kumtong/Brit + Co, photo via Getty)