Yes. There's a perfectly valid Doylist explanation for this (too many branches are a pain to maintain, you have to prune them to manage the game's complexity), but the Watsonian one is weak. If you try to be a mega-asshole to Jaye you get a premature game over, but in the other two outcomes the game interprets it as you being ready to patch things up with her.
I think the problem lies in letting the MC be such an asshole to Jaye at all. We know from the backstory that he's afraid to act on his feelings, so pushing her away after a forced reunion is expected behavior, but we also know that the only reason he does this is because he cares about her and doesn't want to see her hurt. To actually undermine her, to try to cut her off from the inheritance would only hurt her.
The break day could've worked if the MC was simply aloof with Jaye:
- high love - sexy break day as intended
- high trust, low love - Jaye gets the MC to open up and admit he has the hots for her. Then he either convinces her not acting on these feelings is for the better or does the bunga-bunga
- low trust - the MC tries to avoid the break day, so Jaye corners him and lays her cards on the table: she knows why he's doing this, so he should stop deflecting the issue and come clear. Then he either convinces Jaye that getting close to her is too risky and they agree to remain professional distant, or he agrees to become friends again. Or goes straight to bunga-bunga, if you somehow managed to end up in a low trust, high love situation.
