It's been a while since my last playthrough, but, from memory:
Josy is the fastest romantic option early on - you meet her first, date her first, and, of the five main LIs, she's the first to get your dick wet. On the other hand, she's also pulling back a bit in later Episodes - becoming less adventurous and prone to declaring that problems are too hard.
Jill is the slowest to get started, but is getting increasingly wild once you get past her initial reserve and she starts gaining confidence.
Sage is initially keen to get sexual, but reluctant to engage emotionally, but transitions to looking forward to a settled domestic arrangement.
Maya is more restrained than Josy originally, worrying about her father keeping an eye on her, but is significantly wilder once that concern passes.
Bella is resistant to the idea of doing anything with a student, but has experience, a wild girl in her past, and, while she's not exploring new territory like Jill (or Maya), is happy to give you the benefit of her experience once she gets past the idea of denying her attraction to you.
Meanwhile, the Others are generally purely sex to start with, but become increasingly romantic in recent Episodes.
