Time loop of a year, male protagonist, comedy

This is a movie from maybe the 2000’s about a guy (I believe he kind of looked like Jack Black) who is in love with a girl A. He had a chance to be his girlfriend, but he didn’t take it and she gets married to someone else. He regrets his actions. There is this other girl B who is friends with girl A and with the guy, this other girl B is a wedding photographer. The guy gets stuck in a time loop where he does have a relationship with girl A because he had taken one of those chances, every new time loop starts with him waking up in his bed. But in every time loop there is something worse in his life, like him and girl A being punks or something, and him being promoted over his friend, who gets upset about this and they then kind of lose their friendship. He and his friend work in the same office, this friend is black. In this time loop, the guy has also learned Chinese for his job, and he’s really surprised that he can do that. At one point he says in Chinese: “I have no idea what I’m saying right now”, or something like that. He also had balloons in his office for some reason and this friend pops all of them while looking the guy in the eye, and thereby saying that he doesn’t like him anymore.
Over the different time loops, the guy gets closer and closer with girl B, and at one point towards the end of the movie they are sitting in a dimly lit kitchen and he cryptically talks about his struggles to her, about how he seems to start his life over every time or something. She seems to understand what he’s talking about, about this time loop. In the end, he realizes that him and girl A aren’t meant to be, but him and girl B are. They get together.