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: Using my throwaway again, and on mobile so apologies for formatting.

I'm friends/acquaintances with this guy who is 23, turning 24 in a few months. He hasnt had a lot of luck with girls and often comes to me when he has a new crush to gush about them. The past four girls he has developed feelings for have been 18 or 17 and about to turn 18. One was 17 when he started developing feelings and told me he was going to ask her out on her birthday. I told him that I really didnt like that and he got upset that I wasnt supporting him and started that he was waiting and not asking her out before she was 18.

I've spoken about how I feel uncomfortable about it and told him in the end it's his decision as they are legal at 18, but that I wouldn't be enthusiastically encouraging him to go for them. So far all these crushes have lead to the girl turning him down, something I have wondered if it has to do with the age gap, so nothing has come of them. But he gets upset that I dont want to encourage him to go for these relationships.

Tl;dr: almost 24M develops feelings for 18F and thinks it's unfair that I dont encourage him to pursue them.

not approving of my friends age gap crushes