Newly divorced public relations executive Alex (Hank Azaria) can barely keeps things together. His co-worker, Helen (Kathryn Hahn), has convinced herself she has it all together, but she is actually obsessed with her late fiance. After a night of drinking, the two seek comfort in bed together -- leading to a casual (and, unsurprisingly, awkward) relationship between the two. Alex's boss, Stephen, is worried about his employee's emotional stability but needs him to focus on his work. Alex's pals include bachelor Dan, who is in search of a wingman, and nerdy Gregg, the lone husband in the bunch.