I've been on a fair amount of dates last year, but it's not because it was a hobby (although, I guess based on the amount of time I spent trying to get to know people and then seeing them in person, I guess you could say it did add up to actually being a hobby...).
I don't really have many crazy stories, but I did have a bad habit of not being ready for a relationship, mentally, which caused its fair share of problems. Whomever said "boys don't cry" has never tried to break it off with one (or several...). While I'm not exactly proud that that happened, I did need the experience of seeing a variety of different people to get a better sense of what I want out of someone I could potentially spend my life with.
If I had to pick a craziest, I'd say it was the one time I went to a Chinese restaurant. I barely knew what the guy looked like and he didn't wait for me outside so I had to like...fumble around in a dark place to find someone who -looked- like they were waiting for a date to come in. After talking to him more, all of his stories were pretty much about how he got mad at someone, got drunk, and then did something to fuck up their life. One of his stories was about how he had to go to the bathroom in a class he didn't like and his teacher kept telling him "no." He said something like "Well then I'm going to shit on your projector or I'm going to get up and go" to her to resolve this conflict. I thought I was fairly charming, but I never considered telling such a quality story to someone whom I've just met.
The best part, however, was when he was talking about a "hood rat" he had met while drunk who had a nipple piercing in the wrong way (she had it pierced vertically). He asked me if I knew what kind of piercing that looked like (he used that actual name for it, so I wasn't really sure), and when I said "no," he unbuttoned his shirt and showed me his in the middle of the restaurant.
Oh.
After that, he never texted me again which was because, I'm assuming, I wasn't very interesting to him. I never messaged him either because that's about the point in my life I decided I really wanted standards or something idk