Old friends Sean (the family man) and Christian (the playboy) are partners in a plastic surgery office. Their relationship is under fire after Christian operates on a Colombian drug lord who pays him in drug money. Sean's family life is also in upheaval, and he is headed for a mid-life crisis.

Sean and Julia discover Matt has tried to circumcise himself. The business is sued by a faithful client after Sean accidentally leaves a surgical tool inside of her body. Meanwhile, Christian and Grace struggle with a mentally unstable patient.

Sean and Christian learn that they have to take a test in order to continue practicing. Sean and Megan visit a doctor to learn that there is nothing they can do for her. Mrs. Grubman returns to get an operation on her and her fiancé. Christian passes his test, but Sean walks out. Megan commits suicide. Julia finds out about Sean's affair with Megan.

As Julia and Sean's daughter Annie faces puberty, they must both face the harsh realization of maturity and deal with their own issues about getting older. When Gina tells Christian he can no longer be involved in Wilbur's life, Christian is forced to reach out to an old flame in order to build a case to gain sole custody of Wilbur.

After Julia's accident in the previous episode, Julia turns to Sean and Christian to fix her face. Sean resists at first, but eventually decides to do it after Christian lies to him and says the woman that was going to fix her face botched several jobs. Sean tells Julia that he keeps trying to forgive her and wants to try to love her again, but that it wouldn't happen right away.

Julia has an adverse reaction to the anesthesia and dreams during her surgery. Ava shows up in her dream as a different form of life coach, and guides her through this surreal life. Julia is married to Christian, which seems happy on the outside, but is really falling apart on the inside. They run the Troy/Troy partnership firm. When Christian decides to leave the practice, Julia interviews another doctor - Sean, someone she knew from high school. Trying to catch up on old times, Sean invites Julia and Christian to dinner. They meet his wife, Megan O'Hara, and their son Matt, who is on the nerdy side and has a bug collection. Megan is three months pregnant with a girl they plan on calling Annie, named after his grandmother. Julia is upset after a visit to Liz, an OB/GYN in this world, who has two kids. Julia cannot have kids with Christian, who wanted to have a biological child since he was adopted. Kimber, Julia and Christian's three-way partner becomes pregnant, and Christian refuses to get rid of it. We are revisited by several characters, including Mrs. Grubman, Jude, and Julia's friend Suzanne.

When Julia wakes up in recovery, Sean is there waiting for her. She has realized that things would never work out with Christian, and that Sean was always the one she loved.

Mrs. Grubman is back for more Plastic Surgery this time she wants Christian to preform it after she has passed on. Sean and Julia have conflicts over Conor's Surgery.