Well, alot of them seem to be just rumors. Same as the drug one, for example.
And some are probably people exaggerating some things they saw, like when he asked that girl to leave with him to get out of the meet up and then got hit by her ex. Other times, instead of getting into an altercation, he might've been seen just walking away with a girl and then gossiping people did what they do best, you know.
And he did have prior experience, at least according to his chat with ourC and their first time, so every once in a blue moon he probably just hit it off with someone and they went at it. Since he's so easily bored, probably someone that was fun to talk to and then it just escalated because of his cocky/flirty nature

i also rly wanted to know about chaewon’s past relationships/hookups bc how tf did he pull if he’s at home all the time and hates people