Stewart accidentally suffered a hernia and has to go to the hospital for a surgery. While he's waiting to be prepped, the other Barnes family members are suffering relationship problems all around him. As Stewart wonders if the distractions his doctor and his anesthesiologist are having might cause his untimely death during surgery, the rest of the Barnes are wondering if they're cursed to be alone forever.
While Stewart tries to hook Ben up with the new neighbor, he is far too busy keeping it a secret that his ex-wife Naomi has returned and possibly wants to re-kindle the relationship.
Lydia is arranging a bachelor auction and Benjamin feels left out when his mother doesn't ask him to be in it. Oliver helps Lydia to set Regina up with a doctor she has interviewed, but they know it won't work if Lydia shows signs of support.
Oliver and Ben fight over losing patients to one another's practice, while Lydia and Stuart start panicking when they realize they're about to be audited by the IRS.
Stewart ends up being named one of the city's top doctors by a Manhattan magazine. However, he is less than thrilled when his old rival shows up at his celebration party with none other than Lydia.
Oliver, Regina and Lydia all decide to use family member for their own personal gain. Meanwhile, Stewart tries to find a way to get Ben to take his lazy housekeeper.
Stewart ends up in the ER with a backache on of all days, Valentine's Day. Ben somehow gets locked in Crystal's bathroom while she is taking a bath and Oliver tries his best to get out of a Valentine's dinner with his mother.
Stewart and Lydia pretend to still be married to one another while his former receptionist visits. Oliver wants to stop dating a woman whom he finds annoying, but feels horrible because she happens to be friends with Ben.
The whole family gets stuck together in a snowy mountain cabin and the guys find a pregnancy test, but they don't know if it belongs to Crystal or Olivers new girlfriend.
Ben, Oliver and Regina throw a wild New Year's Eve party so they can meet hot dates, but their plans are quickly thwarted by the arrival of their parents. Lydia has invited a handsome man she met at the hospital to the party and has no idea that he is Crystal's father.
Lydia becomes jealous when the kids befriend Crystal, then makes them go with her to visit their former housekeeper.
Lydia and Regina are forced into a cooking class together and Lydia gets friendly with the Chef. Crystal misunderstands a simple gesture by Stewart so he asks Ben and Oliver for advice.
Ben becomes tired of always having to be Lydia's date. To make her confront her fear of dating after the divorce, he tries to set her up with a widowed doctor from the hospital who seems to like her.
Regina and Oliver begin fretting over Ben's new obsession with comic books and his new slacker friends. So the two come up with a plan to end the situtation by setting Ben up on blind dates. Elsewhere, Lydia is convinced that her dog likes Stewart more than her and is none to happy.
The whole hospital finds out about Stewart and Crystal's relationship, much to Lydia's dismay. So to prove to them she is moving on with her life, she throws a party. However, things don't turn out quite like she planned them.
Ben is thinking about flying out to Oregon to meet with Naomi about saving his marriage. However, his family is dead set against it, especially Lydia.