I enjoy Dane Cook, I said it, do I think he's a good actor? No, from the work that I have seen of his, which includes Dan in Real Life, Good Luck Chuck, Employee of the Month, and now, My Best Friend's Girl, I have basically with full-confidence that while he may have something formidable to contribute to the cinematic arts, he hasn't tapped into it yet, or at least, I haven't seen it. However, I like his comedy, I don't laugh during it like I do during Daniel Tosh, and I don't think like I do when I watch George Carlin or Bo Burnham, but I am entertained.
He tells stories, whether they lead to a consistent punch-line is irrelevant, because for the most part, I basically enjoy the ride. He does it with enthusiasm, I guess, and every once in a while, he says a joke that I like.
Anyway,
I didn't expect much from the movie, and surprise, surprise, I didn't get much out of it. The story felt incredibly similar to Hitch, another iffy movie starring Will Smith, it was about a guy that would get paid to help low self-esteemed guys get the girls of their dreams before becoming a romantic comedy. This was about a guy that would get paid to act like a dick to the girls so that they'd "appreciate what they had," and like it, eventually became a romantic comedy.
It wasn't anything special, Jason Biggs was more annoying than sympathetic and didn't feel like he added much to the actual story, Dane Cook has a pompous confidence that I enjoy, but his acting chops are less than stellar. As for Kate Hudson, ... eh.