I never got any of the webcam scenes in my playthroughs, I just figured those were on the non corruption path. But if you choose not to go to the movie theater with them Chris tells you to ask Ann about it and she trys to be scretive but the MC still suspects she's not telling everything but instead of pushing her about it, it just disappears from his brain. Alternatively if you go and put her in a seat with Chris and shake your head no she ignores you and let's him do things anyway. That alone would violate most sharing agreements making it considered cucking/cheating. Also I think somene mentioned on the non control path if you tell her to break it off with Chris she fucks him instead.
You seem to be forgetting something.
Ann had only met the MC thru Vanessa setting them up with each other.
She doesn't even know the MC yet, only that he's a buddy of Joey, her latest guy.
Also, Vanessa had pissed Ann off before when she'd liked some other guy, who Vanessa fucked instantly.
So Vanessa regards men as toys she wants more, if they belong to someone else.
MC and Ann are on a first meet up, which most people would walk away from if they don't click.
The most significant event in their meet up (it's not even technically a date) is when Chris asks for her number, while she's sat at the table, which she gives it to him.
Neither of them are in a relationship of any sort, after all.
Yea, it's rude but Chris does ask and Ann does give her number out.
She's clearly excited being the centre of attraction of two guys she'd actually want to go out with.
The sexual stuff is almost superfluous to the situation of these three characters.
It's like too men engaged in a psychological duel where Ann is there mode of battle.
The cinema scene is based on your decision to share and be in control (or not) at all times.
Ann is her own person, you could argue the cinema is the first proper date, and it involves Chris, because the MC was cool with that.
She's not his fiancé after all, she's the girl she met when some guy he once knew reaches out, and his girlfriend asks the MC to meet her.