Ira Black (Chris Messina) is a wildly neurotic thirtysomething who can't get his life in gear and still hasn't finished his grad school dissertation, he's been in therapy for 12 years, and can't bring himself to settle down with his longtime girlfriend Lea (Maddie Corman). When both Lea and his analyst inform Ira that they don't want to see him anymore, he decides he needs to make some changes. Ira joins a health club, where he meets Abby Willoughby (Jennifer Westfeldt), who is supposed to sell memberships to the gym but is much better at listening to people's problems. The two discover they have a strong and immediate rapport, and Ira asks Abby to marry him only a few hours later. Abby says yes, and soon the couple are wed. However, it isn't until after they've been married for a few weeks that Ira discovers Abby has been divorced twice already, and it makes him very uneasy about their relationship. Despite more therapy, Ira asks Abby for a divorce, and it sends shock waves through their families -- Arlene begins having an affair with Michael (Fred Willard), Abby's free-spirited father, while Seymour commiserates with Abby's mother Lynne (Frances Conroy), and eventually parents and children are all meeting together in group therapy for couples.