Looking back, there were definitely several attempts in my early days of computing from 1999-2003 or so.
One was an on-line snooker and pool game I used go play a lot, probably when I was about 10 or 11. Mostly UK based players, but you'd occasionally get some random tourist from like Kyrgyzstan.
I remember some older guy from London would repeatedly ask for my MSN details every time we matched together, and would always enter my games if I created a new room. I just thought he was an annoying lonely guy back then, but 100% he was trying to make inroads to fuck kids. I ended up never playing that game again after a while.
Also a lot of similar attempts in Habbo Hotel, back when that was a thing. The penny didn't drop at the time, but my natural wariness and scepticism came in and saved me.
Oh, and in real life: I was once waiting for my friend on the corner of the street near his house, as he was due to arrive home soon per a phone call shortly beforehand. I distinctly remember drinking a soda while leaning on a fence, probably about 9 or 10 years old.
Broad daylight, a really old guy (like 70s, maybe even 80s) pulls up beside the kerb, and opens the car door. He kept saying 'are you getting in lad?' while getting increasingly more irate. Scary thing is, part of my brain actually did entertain getting in the car. He ultimately just drove off in frustration.