Brian O’Hara, known for his pattern of serial monogamy, reaches his mid-30s and comes to the startling realization that he’s the only one in his group of friends who hasn’t settled down. While he isn’t opposed to the idea of a lifelong partnership like those his friends have found, Brian starts to question if he’ll ever meet the perfect partner for himself. Complicating matters is his romantic interest in his best friend’s girlfriend, which certainly doesn’t improve his odds.