Oh gosh, so many stories, none particularly "weird" per se, just kind of creepy due to my age in all of them (of course I get catcalled now that I'm older too, but so many happened in my early-mid teens).
My hometown is pretty small, but there are other smaller towns surrounding it that have a few tobacco fields. A bunch of Jamaican men would come up every year and work the fields along with a bunch of other seasonal workers (mostly students) from my area. Every Friday night, they would take two school buses to the mall in the city next to mine (only mall in the area). Friday night was also the night me and my friends would get a ride to the mall as well. Without fail, every single Friday they'd be there, and as we walked by, the guys would come up to each person, or group, or just yell out marriage proposals. It was always so uncomfortable.
Another time when I was around 14/15ish, in my hometown, I was walking to the downtown, and there is this one street that everyone uses to jaywalk across to get to the sidewalk that heads downtown (otherwise you'd have to walk all the way around, entirely out of the way, to the lights and then walk all the way back up to get to the same spot and continue heading downtown [I'm sorry this is really confusing to explain the layout of my town]). So I was waiting there for the cars to go by, and this white van (the really creepy vans- you know the type) drives by, and the guys inside yell out something vulgar. I ignore it, thinking they'll drive by anyway and I'll never see them again. As I continue to stand there after they drove by, I see them immediately pull over to the side of the road just slightly up the street from me. On the side of the road that I was planning on crossing to. So I cross the road, and see them sitting in the back of their van, back sliding door open, just waiting there. And I nope right out of there, deciding to go all the way around to take the other street to downtown. Felt like a kidnapping waiting to happen.
Last one: One night in high school, when I was maybe 16/17? I went to a show (local bands, friends' bands, etc) in the next city over with my friends. A huge group of us crammed into the car to head back to our town, and we got back around 1am or so. The party was going to continue for awhile, but I had to head home because I had some stuff to do the next day with my family. So I was walking down the road (same road as the previous story- there's not many main roads in my hometown) and this "really old" guy (looking back, he was probably only like 28-31 or so, but my oldest guy friends were 24, so anything over 25 was "old" to me.. even 24 was pushing it), happened to come outside his building to throw out some trash or something. He was really obviously drunk, and so he sort of stumbled towards me and was all "Heyyyyyyy, prettay laaahday~ wanna come drink with me and my buddays? How about it eh?" And I just said "No thanks..." and kept walking. He left me alone, but I could just hear him mumbling to himself for awhile about how pretty and beautiful I was.