I've been replaying all of my games and making spreadsheets with info about all the characters (Backgrounds, relations to other characters, how far the relationship with the MC has progressed, etc). One of the stats I keep track of is if the Love Interests first time is with the MC. I have a lot of fun trying to figure it out by going over statements of the character, lines during lewd scenes, etc.
This game has actually been a lot better than most for this. There have been lines in the game that confirm Skylar, Bailey and Kaylee have never been with a guy or a girl and Emily has been with both. There is a mention that the MC was with some girls in high school before he was dating Hannah, so we know his first time wasn't with Hannah.
Hannah however is the one exception. She mentions she's never been with a girl, but there seems to be no mention on whether her first time was with the MC or before she started dating him. We're coming up on the last chapter so it probably won't be answered in game. Normally I'd just fill the cell with a question mark and feel mildly annoyed every time I see it til the end of time, but since Drooskati is active in the thread, I figured no harm in throwing out the question and hoping the author feels generous with an answer.
Obviously it happened before the game began, but was Hannah's first time with the MC or someone else?
