I'm on my first playthrough and it's November 2nd. When it came to confidants I always put most of my focus into people that weren't actual Phantom Thieves members. I don't know why, I guess it was just because I found it more interesting to learn about the people that I didnt spend all of my time inside Mementos and Palaces with.

Well I finally got my first party member to confidant level 10 and I only just now learned about ascending personas. Geez, if I knew that was a thing I would have put a lot more focus into them earlier in the game. Now it feels like I'm getting close to the end, and I'm definitely regretting not spending more time with them! Oh well, I can capitalize on that in my NG playthrough I suppose!