
By Tony Bravo
You know the feeling. You’re having drinks with a semi-stranger you’ve met online or via an app and it’s not going well. All your cute messages and texts leading up to this mean nothing. Now you’re trapped trying to make conversation with someone that you’d run like hell from if you met them on the street.
First date nightmares, brought to you by technology.
The following are real tales from real singles. Names have been changed because, frankly, you’ll understand why they don’t want their names attached to some of these stories. For those coupled, the following stories should reinforce how happy you should be that your first-date days are behind you. For the singles out there, you know what we’re talking about.
One, two, cupid’s coming for you…


At first I just thought she was really passionate about her causes. She was involved in a bunch of things: trans acceptance, LGBT homeless youth, environmentalism, reproductive rights — the usual range of socially conscious lesbian activities. We were having coffee when the topic of animal testing came up. To be clear, SHE brought it up. As she described some documentary she’d just seen on orangutans testing cosmetics in China, she slowly dissolved into a weeping, hysterical puddle of tears. She was really starting to sob. I tried to comfort her but couldn’t get over a feeling of embarrassment — for her, for myself, for the people at the tables around us watching. I feel like it’s a disservice to all women whenever one of us becomes a big emotional mess in public. She got herself together but about 10 minutes later she started thinking about the orangutans again and the waterworks started. When she got up to clean her face in the bathroom I got out of there. Feelings are one thing; being sloppy is another.
“Lisa,” The Castro

We’d been chatting on Match for about three weeks. We both worked in finance, we both went to Duke, and we both talked about wanting kids. We met at a bar on Chestnut. I felt like we were hitting it off well. The chemistry was there, he didn’t seem too arrogant and he was genuinely funny. The only thing I thought was weird was that he didn’t make a lot of eye contact with me. He hardly looked at my face, actually; his eyes were usually cast downward. I have this habit sometimes of slipping my heels on and off when I’m sitting down and sort of dangling my shoes by my toes. It’s a totally unconscious thing and it occurred to me that might be why he was looking down at my feet. I apologized and told him it was just a little tick I had — sorry if it was distracting. It turns out he liked it. He asked if I would mind taking my shoes all the way off; he had a fetish for women’s bare feet and said part of what drew him to me on Match was all the pictures of me swimming and at the beach with my feet out. I finished my drink and finished with him. If he had waited a few dates for that disclosure, he might have had better results. It was a little creepy that he felt comfortable playing footsy out in the open.
“Jenn,” The Marina


I found him on Grindr (yes, gay guys can meet on Grindr for real dates!) and we decided to grab a beer. The first part of the night was fine. We had a couple drinks, walked around the neighborhood, and ended up back at his place. That’s where things… just listen.
He was a taxidermy enthusiast. He didn’t just collect the stuff, he actually MADE it. He said he had turned part of his garage into a workshop and that while occasionally he gave away some of his “projects” as gifts, most of the things he worked on he was too invested to let go of. Badgers, raccoons, a couple cats, squirrels, ducks, and even what looked like a kind of terrier all occupied his living room like some kind of necro-zoo. No, I don’t know if he had any of his projects in the bedroom — you think I was going to stay? It was bad enough having all their dead eyes staring at me with my clothes on.
“James,” The Mission

Eve and I had a great time. Drinks led to dinner, dinner became more drinks; more drinks became another round of drinks. Maybe we were having such a good time because by 9:30 we were both well on our way to being drunk. She took me to her place and we started fooling around on the couch when her roommate came in. I don’t know if it was the alcohol or if there was already a problem between the two, but the moment she saw her roommate Eve started screaming at her. “You told me you were staying at your boyfriend’s, I never get any time here, for all the nights I’ve had to listen to the two of you banging that headboard against the wall I can’t have one night?” It was like a switch flipped and Eve was a totally different person. Clearly, this had happened before. The roommate started screaming right back at Eve without hesitation. After about a minute Eve started picking up books from the coffee table and throwing them at her roommate. I decided that was the right moment to put on my shoes and go.
“Thom,” Lower Haight


She was an actress so I was already a little hesitant to go out with her, but she didn’t seem like “one of those” kinds of actors. I met her for dinner and she seemed down-to-earth and not so “actress-y.” Maybe that was her greatest performance of all. After some small talk and once we had ordered, she opened up to me about this amazing thing that had changed her life: the Church of Scientology. After sitting through about 10 minutes on how the church cured addictions — the way it was misrepresented in the media, how her acting teacher had brought her into the church and saved her from her own negative thoughts about her mother — she then started to pitch what the church could help me change in my life, based on what she perceived as flaws on my OkCupid profile and in our messaging over the last week. Everything she said, even the most cutting dissections of my personality and decisions, was said in a strangely even, but cheerful voice that reminded me of a preschool teacher. When we had messaged previously I had told her I had PTSD from having been in an almost fatal motorcycle accident. She started to lecture me on how psychiatry was making me think I was sick and that there was no such thing as PTSD. I got angry and left. For a week after, she kept messaging me. She was sorry for the misunderstanding and would like another chance. I never acknowledged her messages, but about three months later I saw her in a small part on a television show. I guess it’s true what they say about Hollywood and Scientology.
“Kennedy,” Pacific Heights

The date was pretty good — dinner followed by drinks. When we got back to my apartment things got weird. We started making out and within five minutes his nose started to run to the point where we had to take a break. I asked him if he was okay. Was he allergic to my cat or something? He said no, it’s a scientific fact that for some guys if they’re turned on by the pheromones of someone they’re in contact with (in this case me), they have a reaction where their sinuses engage and their noses run. Thank you? I tried to take this as a compliment but the constant sniffling and dripping meant he kept excusing himself. After about the fourth time he went off to blow his nose I jokingly asked, “Are you sure you just don’t have a coke habit?” He was not amused and left shortly after, leaving a trail of crumbled tissues in his wake.
I’m still not exactly sure if he was on coke or if he really did have some sexy allergic reaction to me.
“Mario,” SOMA



I had listed roller skating as an activity in my profile so he suggested we go on a skate date. I met him on the Embarcadero and I was surprised at how pristine his skates were. It turns out he had never skated before. Within a half hour he seriously hurt his leg in a fall and we were in the back of an ambulance. His leg was broken in three places. He was in a lot of pain. We hadn’t really had much time together before the fall so I didn’t know much about him. The paramedics pumped him full of painkillers and kept trying to get information out of me. Who should we call, does he have insurance, any medications, allergies, etc. I kept explaining the situation to the point where I felt like I was in some romcom meet-cute from hell. I wasn’t even comfortable enough rifling through his wallet, and his phone had a pass code so I wasn’t much help. Eventually, when he was a little more coherent he told us who to call. In total, I spent 10 hours with him. I figured I’d give him a few days before sending a message to ask how his leg was and, you know, to give him an opportunity to thank me for staying with him. Here’s the best part: He deleted his profile and never got in touch with me. You’d think an experience like that would have bonded us.
“Leslie,” Russian Hill

We had been talking at the bar for about 20 minutes when he suddenly said he wasn’t feeling well. He excused himself and came back a few minutes later looking significantly better. He seemed to feel fine after that. We were chatting about his growing up in New Hampshire (strange, the things you remember) when suddenly his hand shot up over his mouth and he started vomiting. The hand wasn’t really doing much to block his spray trajectory. I jumped back as he hosed the front of my dress. The worst part was I had borrowed my roommate’s vintage satin clutch, which he managed not to just puke on but somehow also in. It was a small bag so it filled up quickly. He obviously felt pretty bad and kept apologizing (once he was done, of course) and kept saying to send him the cleaning bills or whatever. I bought my roommate a new purse myself. To have further contact for either one of us after that, our accidental Roman shower, would have been one indignity too many.
“Candace,” The Presidio

Misery loves company. Share the best of your worst dating app stories in the comments section. Any nightmares top these? Did you find out you were dating a cousin, get kidnapped by a sleeper cell, have to fumigate your house after a date left? Tell us! Unpleasant dreams, singles — see you online.
Illustrations by Jon Stich.
