Definition: Given a real-life anecdote of a complex ethical situation, generate a suitable title that describes the main event/root cause of the situation. Imagine that the given text is a social media post, and you have to write the title of the post, so the users can decide to read the main text or not.
Input: So HS was a weird time, my friend and I were really nerdy and didn't start doing any of the normal HS things (sex/drugs/drinking wise) until our senior year. Basically she randomly decided in the winter that she wanted a boyfriend and she picked this guy who had quietly liked her for two years. She constantly told me the relationship was awkward/not serious but that they were both trying it out and having fun because we had been so sheltered for so long. Thing is, he was madly in love with her. That's not saying he "deserved" more or any of that r/niceguy shit because if she doesn't have feelings for him she doesn't, and she shouldn't be expected to manufacture any for his sake! But I think she actively denied *his* feelings so she could use him to gain experience basically. They broke up a bit after prom, stayed in touch for a bit over the summer, would sometimes say hi if they ran into each other at the same party over summer/winter breaks, but really don't speak anymore as far as I know.

I ran into him recently because we both happened to be in our hometown visiting our parents around the same time. Turns out we're both looking to head back to school within a year or two and actually have very similar research interests despite coming from kind of tangential majors/industries. We also have remarkably similar political views, like a lot of the same books and movies and music, both like camping...it's like a REALLY good fit. So we've been hanging out a bit (turns out we live in the same city as well, he just moved here and I've been here for almost 2 years), nothing explicitly romantic, but I really like how it feels and was thinking of asking him on a real date. Idk if he would even say yes, partly because it's been really platonic so far so maybe I'm misreading things and partly because of course he knows about my friendship with his ex, and of COURSE I would talk to her about it before doing anything. I'm only even considering it because their relationship was so, casual almost? But WIBTA?

asking out one of my best friends from high school's ex