The comically six worst online dates I've ever been on

#350 Comic Relief – Virginia Albert – 4//10/2026

This week’s prompt: Write a story with the goal of making your reader laugh

The comically six worst online dates I’ve ever been on

In 2026 and years preceding, every single person with access to a Smartphone or even a computer felt the weight, the gravity, the nagging tug, the loneliness, the candy flipper, the seductress, the home of my future husband? – all in the form of dating apps. When you go on the App Store, there are more dating apps than in any other category, it seems. Apps from interest groups, ethnicities, many of which have not fully taken off, but that’s the hustle, right? The hustle feels so overwhelming at times. There are so many people on the apps, all different forms and sizes and hair colors and ethnicities, that using apps makes the whole experience that you start once, thinking it will be amazing, incredible (!), you’ll find your soulmate, and you end up finding 5’5 guys who live at their parents house, never graduated college, work in some obscure field… and after this happens again and again, you’re supposed to say, “Can I have more please?”

Oliver Twist, no. You do want more, but you want more in the right way. No one meets in real life anymore, everyone says, stuck to their phones waiting for someone magical to appear and transform their existence from grocery store/drug store – it never happens, so dating apps are all we seem to have until something potentially comes along.

Here are a few of my worst online date stories.

Guy shows up at the bar (King Tai in Brooklyn, New York) and immediately starts talking about his children and asking me how many children I wanted to have. It was for a casual drink. He then said he had 12 children and wanted more, so he was curious about the max I could go with having his kids. This was all within 5 minutes. I chugged my drink as fast as I could and ran home as fast as I could, beyond creeped out, and a nice primer to the wonderful world of online dating. The date was so bad that the wait staff at the bar actually came over after and asked if I was okay because the guy was so weird—they could tell I was like “what the actual fuck.” The whole time.

At King Tai a few months later on a Friday night around 5pm, a regular would not stop proposing marriage to me and convincing me, without knowing each other, why would we would make a perfect pair. He insisted for an hour, and again, the people working at the bar had to have me climb out the back so he wouldn’t follow me home (apparently, his name is Andrew and he does this to other women.) I was so freaked out and so appalled but laughed so hard at the sheer desperation of first-date meeting serious marriage conversation – the audacity/ nerve to think it could possibly work. They never let me live it down. They always teased me about the Andrew marriage plot and I would just make faces to say “FUCK NO” in return.

One time in Houston, I met up with a choir teacher who lived over an hour away. I felt bad that he had come in town so far for just a scoop of ice cream, but he did, and he picked me up in his car and we drove down to Amy’s Ice Cream, a common ice cream parlor in Texas. This guy was so depressing. His entire family other than his sister had died, so we spent 45m talking about the death of his family and everyone in it and how he had no support in Houston or really anywhere and how much it killed him to essentially be an orphan. This was not first date material, and it made me so sad, I didn’t want to go out with him again. His hair smelled like head & Shoulders dandruff shampoo, he had flakes all over his black shirt, and I really felt like an asshole for not wanting to go out with him again.

One guy I went out with did not have an esophagus. That was really weird. He had to swallow water with a cup that did not work very well as his esophagus would not allow him to drink or eat normally. Pitcher after pitcher of water, realizing he was still married and not yet divorced, as well as living over an hour away as a children’s choir school teacher, I had no choice but to leave. The combover reeked of something that I could not put my finger on, but I knew I did not like it. He was a nice person who had traveled too far for a picky bitch like me.

Another first date I went on—he was 24 so it was a low-stakes endeavor—we went to Sonic and got ices. Then immediately drove home. There was little to no banter. He was an absolutely tiny guy – maybe 5”4’—who had misrepresented himself in his photos so that one was more on him than me.

The big enchilada. This guy from Houston a few years older than me who went to a respectable public high school (Lamar) kept asking me out over and over again on Bumble. I kept ignoring him thinking I wasn’t very interested, no matter how nice he seemed – I just wasn’t interested for some reason. His persistence paid off when we agreed to go eat Mexican food. The food was delicious, but the conversation quickly turned south (not of the border) when he told me:

I live with three cats, three dogs, and three goats all in a tiny one bedroom apartment.

Do you want to come over and watch a movie and fuck around my animals?

Do you have any condoms? Wait – you don’t want to come over? But, I want to watch a movie. We don’t have to…I mean yeah we will have to…

In conclusion, it was nice to meet everyone and I wish them all the success in life.