It’s unsettling how common that sort of story is, and it’s always something of a boast, too. “I never gave up! I ate dinner at the diner she worked in every night until she agreed to go on a date with me, and now we’re married!” Even as a “success” story, it’s not exactly great to think that the only reason they are together is because one partner “wore down” the other.
Dude is probably good looking so it doesn’t count as stalking
Edit: guess I’m showing my age and people don’t remember this video
There are plenty of traditionally good looking men, and women, who are considered to be creepy. It takes slightly longer for people to acknowledge it but it absolutely happens. There are also many people who are “neutral” where their attitude flavours their looks. If they’re creepy they’re sleezy and if they’re respectful they’re put together.
To be honest the “ugly” people I know who’d be considered creepy very quickly a) are being creepy and b) haven’t even attempted to make themselves presentable.
Polar opposite experience for me. The guys who look creepy are quite nice and there’s some absolute assholes who are pretty. Ofc the other way around as well.
In my opinion looks say zero about a person and there is no significant correlation between being creepy and looking creepy. Same for looking authentic and being authentic. Honestly I experienced a small correlation in the other direction, but not enough to be informative.
What matters is the signals she gave him and how he read and responded to them.
If she gave signals of “please leave me alone” then whether he’s creepy or not depends on how he responded, regardless of how he looks.
Him being a positive and personable presence near her over a stretch of time, especially if she gave signals of being in the neutral-to-positive range towards him, is fine. The most important thing is that if he eventually shot his shot - and the response was “no thank you” - that he accept this answer gracefully.
Lots of women actually prefer to meet guys through their social circle because it’s an easier way to meet guys who their friends can give their own impressions about and who are less likely to be assholes. It sounds like it turned out well here, although we’re missing a lot of information.