There is nothing more annoying to a girl than a guy who is as desperate as the one in this game. Constantly asking for her number, for her to come back to the apartment, etc is pathetic.
There is no reason to repeatedly trash on the larger girl. Just because a girl is not stick thin does not mean she is any less of a person. Not only that, any girl would pick up on bad vibes toward a friend. It is obvious that you did not take the time to draw her properly (especially when the main character asks her for her name and what drink she wants), which shows that you are lazy. If you want to make a good game, all characters need the same aesthetic quality. You made her left eye considerably lower than her right and her expression is just sloppy.
Your objectification of women is sickening, to say the least. "In her mind...being yours." A man who has said nothing interesting will not get a girl to follow like a puppy on a leash.
"If she does she is probably strong willed." The way you did this made it seem like you were criticizing her.
Hell, you even objectified men. "Gabriel" and his wingman are generic jackasses that only drunk sluts would pay attention to. Controlling, horny, no personality, and clearly trying to split up the two friends. Girls do notice this kind of behavior.
If you are going to make a dating sim, and especially one that takes place in a bar, you should probably try using these lines on various women in real life. I promise you, nothing will happen. Unless she is the sort that is "taken home" every night.
It is difficult to tell whether or not Gabriel just wants some pootang. Yes, multiple references are made about wanting to nail her. But why would any man go through the motions of getting her number and attempting to charm her if that was all he wanted? You might as well leave that to the Meet N Fuck folks; they do a better job at it.
I found nothing enjoyable about this game.