Random Bad Dates from my 20s

I’ve been trying to throw things away to make room for more, but can’t seem to get rid of things like my old scrapbook of “Crushes, Dates, & Loves”. I should hand this down to my daughter, as I’m sure she could appreciate some of these stories. Some stories I barely remember – or not at all.

No Money Man:
This was supposed to be a weekend getaway, but it turned out that I couldn’t get away fast enough. Probably in my early 20s, I was invited to spend the weekend in another town. There was no chivalry whatsoever. He would walk at least 3 to 5 steps in front of me, sat down at the dinner table before me, didn’t bother to open car doors, asked me for money, “joked” by saying annoying, sarcastic, demeaning things, and would put his hands on me in public to show that I was with him. On top of it all, I ended up paying for dinner! Apparently, I never saw this person again. Why don’t I remember this person? Probably because I didn’t want to. He sounds like a total douche!

The Meat Packer:
He never became an actual date, but I saw him at least weekly, which made my grocery shopping more enjoyable. This guy worked at Publix’s  meat department, and we shared the same name. He’d flirted with me on several occasions, always making conversation, but he never asked me out. I was a single mom at the time, going to college and working a job or three. Meeting decent guys was difficult, because in those days “nobody wanted to date a woman with a kid (except maybe old men).” So I finally got the nerve to ask him out instead. His response: “I don’t think my girlfriend would like that very much.” I was pissed and embarrassed, so I started shopping at a different store. Sorry, Publix!

Stinky Pillow Guy:
Back before Tinder, Bumble, and Match, people used Yahoo Personals. I was in my mid to late 20s when I met a guy that lived about an hour or so away. He was very polite and very sweet, even in person. We got to know each other for a few weeks online and by phone, and when I met him, I liked him. Since he lived far and I didn’t want anyone at my house (it was also much easier for me to run far away!), I made plans to stay the night at his house – on the couch. Our date consisted of me giggling at the fact he didn’t have many table manners, but it wasn’t because he was rude; he was just inexperienced. We went to a sushi restaurant where he proceeded to wipe his face with the o-shibori that was presented to us at dinner. Then I watched him butcher sushi rolls with a fork, because he’d never eaten it before. We then rented movies that he talked through them the entire time. Finally, I prepared to sleep on his old pullout couch with an awful back bar that just about crippled me. Then he gave me a nice moldy pillow for my head, and I immediately suffered an allergy attack. Last, but not least, I guess he assumed he was going to sleep with me and took it upon himself to jump in bed next to me and put his measley hands all over me before he started snoring loudly. I managed to ease my way out and left in the middle of the night and never turned back.

The Pilots:
I live in an area where there are a lot of flight schools nearby, so whenever my friends and I went out, we’d always meet pilots. I was probably in my late 20s when I met a pilot from Venezuela. He was in his 30s, and we hit it off immediately. I thought he had a lot of class, intelligence, and was attractive – much different from the down-home Florida cracker types I was used to meeting. He’d told me he’d been divorced for 7 months, but hadn’t been together with the wife “in a long time”.

I was really looking forward to getting to know him better, but after the crooked married cop situation, I decided to do a little research. Lo and behold, there was no divorce. When confronted, he became defensive and thought I was being ridiculous. I told him to call me when the divorce was final. I got a call from him a few months later at the beginning of the summer, and supposedly the papers were signed. Then the asshole stood me up for a date.

At the end of July, I bumped into him at a club where he introduced me to his new girlfriend. Four months later, they were engaged. Fly away, birdie, fly away!

Another pilot I met at a Best Buy while we were both arguing with the jerk at the computer repair dept. He was sort of a foreign guy, seemed really cool, only a couple years older, and he was kind of hot. The first night we went out, he said, “I think I could fall in love with you.”

That was waaayyy too soon for a first date, and it completely scared me off, so I never called him again. I saw him around a few more times, and he thought I hated him. I didn’t hate him, but I was certainly not ready for the “L” word either.

Do you have any fun dating stories you’d like to share? Send them here!

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