The 10 Worst Dates I’ve Ever Been On, Ranked

The 10 Worst Dates I’ve Ever Been On, Ranked ©iStock/a-wrangler

It goes without saying that not every date will be a success. Even if the first few dates look promising, there’s nothing quite like a dating disaster to quickly end a blossoming relationship. After all, there are certain things we shouldn’t have to put up with on a date. The only saving grace is that we can laugh about it afterwards with friends. Here are the 10 worst dates I’ve ever been on, ranked:

  1. The keen gardener. I’d arrived at this guy’s house in the afternoon with tickets for a gig I really wanted to see. The plan was to go out for a couple of drinks first – or so I thought. He was out shirtless in his garden, covered in mud, and digging with a spade. He said he just had to finish off, so I waited, and waited. The start time of the concert passed, and he was still gardening. I told him if we left straight away, we’d still catch a bit of the band. By the time he got changed and we walked into town, the concert was over — we’d missed it. I didn’t see him again after that.
  2. The under-ager. Looking back, it seems like EVERY date was terrible when you were a teenager. This one particularly stands out in my memory, because I was a couple of years older than the guy, which meant I could drive and he couldn’t. I think we went on two dates, where I would pick him up in my car, then we’d park in the shopping mall car park. I’m not even joking – that was our date: sitting in a car park.
  3. The other young guy. I decided to give this guy another chance because he invited me to his work’s Christmas party at a fancy hotel. He promised me everything was paid for, including the room and a three-course meal. When it actually came to checking into the hotel, he made some lousy excuse and told me that I’d have to pay half the money. I didn’t have any other option, as we were stranded way out in the country.
  4. The wannabe stoner. I’d liked this guy for ages, so I was excited when he asked me around to his place to smoke a few joints. It sounded like a pretty cool idea, and I was looking forward to the date. We smoked a joint out the bedroom window, then suddenly his face turned white and he looked ill. He stumbled out the room to the bathroom. After about 10 minutes, I went to check on him and found him on the floor, naked and covered in sick.
  5. The older guy with issues. When I was 23, I ended up dating a guy who was much older than me, who had an ex-wife who still had a key to his house. She would walk in and out whenever she liked, to use the washing machine (apparently she didn’t have one of her own). Each time I was out on a date with the guy, she would text and call him – problems at the kid’s school, the washing machine had broken down, etc. As if this wasn’t bad enough, the guy would answer these nuisance calls during our date, or spend the entire evening texting his ex-wife. Dating 101: turn off your phone!
  6. The soap-opera fan. Officially the quickest date I’ve ever been on. I’d liked him for ages, and was really excited when I received a text asking me to come around to his apartment. My stomach was in knots with excitement, as I hoped that as soon as we closed the door, we’d start kissing and ripping each other’s clothes off. I was wrong. He sat on the couch, flicked on the TV, and started watching Hollyoaks (For those who don’t know, imagine the UK equivalent of Sunset Beach). He was more engrossed in the TV than he was in me, so I left after 20 minutes.
  7. The party dude. I had arranged to go out for drinks with this guy and was meeting him at his apartment first. When I arrived in the afternoon, his living room was still full of people from the night before, completely wasted on drugs. He was wearing pajamas and the dining room table was all smashed up in the corner. Needless to say, the date never actually happened.
  8. The man with the eyelash. There wasn’t really anything wrong with the date, apart from the fact that the guy had one really long eyelash. No kidding — it was well over an inch long, and because it was a bright day, it kept glistening in the sun. I couldn’t take my eyes off it the whole time.
  9. The serenader. I was sitting having a few drinks in a bar with this guy, and a song he liked came on the jukebox. He dedicated it to me and held my hand while singing it to me, gazing lovingly into my eyes. The only problem was that he kept spitting all over me as he sang… and we’d just met.
  10. The master chef. This guy really wanted to impress me by cooking a lovely meal. However, when I arrived he had made moules marinière, and the only food I’m completely allergic to is mussels! I didn’t want to be rude, so I ate a few of them, and just pushed the rest around my plate to make it look as though I’d eaten more. About an hour later, I was in his bathroom vomiting.

Recalling these horror stories, I’m actually glad to be in a relationship now, where I don’t have to put myself through the process of dating anymore. At least I can laugh, and I hope my experiences made you laugh, too.

Ailie is a freelance and creative writer living in Scotland. When she is not busy writing, she will likely be found taking part in political protests, competing in muddy obstacle courses, and climbing mountains. https://ailiewallace.com