There was the "fish" incident (it's also the reason I no longer swim in the ocean). So, once again in Florida, I went on a date with a guy who took me to his favorite beach to swim. We get in the water and I get out about chest high. I dove under the water, opened my eyes and saw a big ass fish in front of my face. My brain went "SHARK!" and I came up out of the water screaming, swallowing half the sea, turning red, snottering, etc. The guy calms me down and asks what the hell is wrong. I looked at him and went, "there's fish in the ocean!" Not my finest moment.
At some point I met a guy who played Warcraft and was a medical student at Florida State. We decided to get together and hang out. Nothing serious, just talked about gaming and watched some movies. Then happened a few times. There was absolutely nothing serious there, he was just really fun to hang out with. Anyways, this ended after the cookie incident. I'm one of those people who like to send something to friends or family who are down. His schooling was hard, he was stressed and pretty unhappy. So I went and ordered a bouquet of yellow smiley sugar cookies. Everyone likes cookies, right? I think I had something to the tune of "I hope this at least makes your day a little brighter" or something super "friendsy". Really, this was NOT romantic. It's something I've sent to my BFF when she was having a moment. He calls me, yelling at me that we were just friends and it's not serious enough to send gifts and that it's over. Nothing says I want to marry someone 5 years my junior like emoji smiley cookies with the most generic "cheer up" note.
Then there was the cake guy. This guy I met off friend finder waaaay back in the early 2000s. He was looking for someone to dress up with and have cake parties. He was a gamer and I thought why the hell not. So I go meet up with him. Dinner was great, he was funny and I really enjoyed myself. He invited me back to his place for a cake party. What's a cake party you say? We dressed up in horrible 90s floofy prom dresses, put on wigs and other outrageous accessories and then smashed cakes in each others faces. While I'm sure it was some sort of weird kink for him, it was really fun. And, he wasn't trying to get me to stalk his ex girlfriend so win. We stayed friends while I lived in Florida and whenever I ended up in Orlando he'd come up with other weird things to do (like going to the thrift store, buying a wardrobe and then doing a fashion show in Walmart -- I'm sure we gave the Walmart people a run for their money).
Then there was furry guy. I think this one was kind of the cherry of all the weird, awkward dates. So I'm one of the nerds that LARP. I had joined a game up in Orlando and started making friends and hung out with them from time to time. At some point, one of the guys asked me out. The first few dates were ok. He was an accountant, the most exciting thing about him was he played Warcraft and played in this LARP. Nothing weird (to me), just a little boring. Or...... so I thought. After a few dinners and movies he invites me over for a horror movie night with his friends. I was going to meet him at his friend's place. So I get there and I'm met by a room full of people sitting around this big room in fur suits.

So we sat there, in the dark, watching movies like The Ring. Me the normal person with about 7 people in fur suits. There were a few more dates but since I wasn't into the furry thing and he did all of the conventions and meets... it didn't work out.
And finally, there's my husband. I met him in the early 2000s playing Everquest. At some point our guild mates told us we needed to meet each other so he flew from the Netherlands to Florida. At some point a Harry Potter movie had come out and we went, but we went to dinner first. He picked a place called Chili's. It's one of those restaurants that has things like nachos, fajitas, ribs, steaks, etc. However, they were having an "all you can eat" rib special which my husband got. On top of that he fell in love with American non sweet iced tea and got that everywhere we ate. I'm not sure how many plates of ribs he ate, but at some point the waitress just plopped down a pitcher of iced tea since he was going through it so fast. On top of all of this, he finished my dinner AND had dessert (at that point in his life he was tall, thin and had a black hole in his stomach). Really, he horrified both myself and the waitress. Well, we go on to the movie. Since it was something like 2.5 hours I got a big 80oz (2.3ish liter) cup of diet coke because I didn't want to leave to get a refill and I thought we could share. 30 minutes into the movie I went to take a sip....empty. WELL.. about 1.5 hours in he leans over and asks when the intermission is. I look at him and go "intermission? WTF are you talking about." This is when I could see exactly when the penny dropped and regrets were had. He didn't want to miss anything but he couldn't sit still. As soon as the credits rolled that man was up out of his seat, knocking granny out of the way and was out the door. He was the first into the bathroom, last out and I still to this day swear I heard a scream. ;-D There were other incidents the month he stayed with me, but this is the one that stands out. LOL