Jewtopia had some really hilarious scenes, along with some uncomfortable ones. REALLY uncomfortable ones, like the guy (Christian) saying offensive things (without realizing they were offensive, mostly because he is kind of clueless on the social scale). The bigger, unredeemable problem, is that after he says the offensive things, he calls the woman (Alison) about 20 times, and she tells him to not call her anymore. So Christian gets his employee friends to help him stalk her parents, as part of the effort to win her back. BOY MEETS GIRL, GIRL REJECTS BOY, BOY STALKS HER FAMILY, BOY WINS HER BACK: BAD FORMULA. AND IT DIDN'T HAVE TO HAPPEN. He could've only called her a few times, realized he was being rejected, moved on to the manipulation (still a little slimy, but completely forgivable in this type of irreverent comedy). Even giving it further benefit of the doubt and saying an irreverent comedy CAN go that far, going that far is what took it from funny to uncomfortable, and therefore less funny.
