A really solid, promising start to the game. The characters are engaging and you quickly care about them, and it's nice to see a decent amount of character development involving people the MC is (presumably) not going to bone.
My one nitpick would be that the MC is just that little too much of a sad sack. I get that he's meant to be adorably socially awkward, but he's no virgin either. Kelly isn't exactly being subtle in the bar, and having him stay clueless all the way to her house stretches disbelief a bit too far.