Hal Larson (Jack Black) is a nice guy, but he has one flaw: he is a superficial man whose fixation on the physical beauty of women gets in the way of seeing their inner beauty. Hal and his equally shallow friend, Mauricio (Jason Alexander), spend their nights obnoxiously hitting on beautiful women at nightclubs and mostly they end up getting rejected. Hal's work life is steady, but he is dismayed after being passed over for a long-sought promotion. His love life is non-existent, as seen when he tries to ask Jill, his attractive neighbor, out for a date. Jill is not interested as she finds Hal too shallow and is not attracted to him.