There's a saying (which could be specific to my country) about men approaching women. If you're handsome it's called flirting, if you're ugly it's sexual harassment. Joking aside, I do notice that successful men (again, maybe specific to my country) tend to be attractive and they usually have an attractive and smart partner. Successful but not attractive men can still have either attractive or smart partner (or both,…
You've got it backwards. In both cases what makes it harassment is continuing to push when it's unwanted. Why you seem to see a difference in results based on attractiveness is because your average guy can't take a hint no matter how attractive they are. So "success" becomes literally stochastic because guys never back off (and bonus take being unresponsive, ignoring them, or outright telling them no as "playing hard to get") so it only works when coincidentally the feeling of attraction is mutual which is sorta related to conventional physical attractiveness but not as 1-1 as it's made out here. 95% of the time I don't want even the hot guy approaching me and even 1/20 feels high.
I kinda wish it worked like Brazilian steakhouse rules where I could wear something that signaled, "open to being hit on by strangers."