So, there's something to be said about Pinkcake's way of presenting this update, and it's that he's making it very clear that a choice is coming for where our MC stands. Is he going to look for a solid girlfriend(s) or keep his fuckboy status going?
In my mind it only really comes down to two choices that are robust. I wish that some of the side girls were not side girls, because I like them outside of that role (Mona, Camilla, Rhionna, Nicole). But of the Main girls, the way I see things are like this:
Bella: Is a non starter. Yes, she is smoking. But she's damaged. She can't sort past the stuff with her husband (whatever that is, he's probably dead) and it's affected not only her mood but her ability to feel emotions at all. Before she could ever be in a serious relationship again, she'd have to get past all this internal guilt she has. This is a doomed relationship.
Sage: Again, this isn't something with a lasting foundation in my opinion. You're a fuck buddy, at best you're going to end up best friends with benefits. If she tries to start a relationship with you, it's going to end badly because you're the rebound. There's also the issue of College. She's on her way out. She's writing her dissertation. She's on her path to graduation. So you have the year with her, at best. College is pretty much over for her, and you're one good last fling.
Now for the others:
Maya and Josy: If you pick this, it could work. But that's just it. You have to pick the pair. They belong together themselves, whether you belong with them is another matter all together. Now, I can't see them cutting you out of their lives, you've clearly become important to both of them. But you don't get a choice of either Maya or Josy because the relationship just won't work without both of them keeping the group honest. (They've both lied and gotten a lot of second chances on their own, it'd be hard to trust one of them).
Jill: She is, in my mind, the best choice but also the worst choice. Jill is caring, compassionate, kind, loving and sweet. She doesn't have a mean bone in her body, so she can't see bad in anyone even if it's right in front of her face. She looks past all of Tybalt's crap just like she looks past all of yours. But Tybalt has made it clear to her that if you keep seeing each other he's going to make your life hell legally speaking. So while Jill herself is a goddess among dirty mortals, the Devil behind her is waiting to catch you together and ruin your life.