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Definitely not as bad as some of the others mentioned here, but when I was 18 a slightly older coworker who had a crush on me for a while asked me out. I said yes because I didn't really know how to say no at the time. I wasn't physically attracted to him, but he was a really nice guy and I didn't see the harm in giving him a chance.
We'd already worked together for about a year then, so he knew a few things about my interests. He wanted to plan the whole thing and surprise me with where we'd go. We agreed for him to pick me up from my house at noon. I thought, "great, lunch date"; they're pretty chill/non-intimate.
So the day comes, he picks me up and we start driving. He tells me he's taking me to the natural history museum. In DC. Over an hour away. Far for a first date, but I love that museum so I go along with it.
We get there, wander around, chat, and after a couple hours walk out onto the national mall to some random food truck, grabbing a nearby bench to people watch while we ate. I wasn't feeling a connection, however, was patient and respectful, after all, we had a good enough time so far, and he put effort into planning this.
Now, normally, after the meal/activity is complete this is when a day date starts to come to a natural end. At this point it's past 4pm, so I suggest we head to the car, thinking to myself that it's a long drive back. Surprise! He tells me he got us two tickets for DC United that evening. Not a huge sports watching fan, I didn't know how to react. Being young, inexperienced, and afraid to upset him I feigned excitement.
He drove us to the stadium, parked, then got out to get something from his trunk. Another surprise! A cooler of Smirnoff ice. After the weirdest tailgate we go into the stadium, watch the game, get hotdogs, and the whole time I'm dreading what other surprises he has in store. He seemed so normal before.
Luckily, after the game he finally took me home. I don't remember what time it was, probably around 9pm, I just remember feeling relief at the sight of my front door. He tried to kiss me when dropping me off, but I managed to avoid any physical interaction. Looking back, it was the weirdest, cringiest date, and the main reason I always drove myself to dates from then on.