Hey, I'm glad you found the game entertaining overall!
This game is a lot on the comical side, that's why some situations might be "exaggerated" (literally for the lulz).
On a more serious note, precisely because the LI is intoxicated from the wine, Monica doesn't feel like she can act on her feelings. She can't possibly know what Jacob really thinks about her. She has many moral qualms both because it's partly a comical situation and partly because she respects Jacob's boundaries.
However, if you managed to reach the ending 5, you will unlock a bonus scene where they're both sober and something happens (with everyone's consent)...