It’s cute because they ended up together. If they didn’t end up together this would read as a stalker story
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.
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.
Unless he realized she wasn’t interested and left her alone after that! That’s the normal, healthy thing to do!
This always reminds me of a comic I saw a long time ago. Two girls are gossiping and one talks about this guy that smiled at her (like packing her groceries or something) and she said he was creepy and stalking her. The next few frames show those same girls recognizing a guy sitting in a dark car watching them through the window and gush about how cute he is and it’s so sweet that he is so into one of them. I can never find the comic… but yeah, it’s all down to how the other party feels.