I did do that once, actually. But I think the big obstacle with Leo is that he won't do something like that on his own initiative. As of the source material, he's already convinced himself that Chase is the only chance he's ever going to get, so I think he wouldn't try again with someone else unless someone made him do so. And this might be unfair to characters we never actually see, but I'm deeply skeptical about claims that Leo's parents are in fact supportive. We really only have Leo's word for it that they are, and Leo's not a reliable source about the feelings of people he cares about, and given his conservative upbringing, and my own extensive experience with "conservative parents think that as long as they're not being as homophobic as they could technically be, then that's the same as being supportive" as a phenomenon, I think distancing him from his parents a little ought also to be a priority.