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Worried about his career, Ryan heads to New York to pursue an opportunity; the group begins to crumble as its members start to complain that they aren't getting enough out of their sessions.

Go On

Urn-ed Run

Ryan is unsure what to do when he receives a flirty, drunken call from his secretary; Lauren comes to Ryan for advice.

Fast Breakup

Anne sets up Ryan with a new acquaintance, a beautiful woman (Courteney Cox) who recently became a widow; Lauren accidentally steals a man away from Yolanda.

Matchup Problems

When Ryan's professional success still doesn't bring him happiness, he tries to find it by helping Danny get Sonia; Owen and Anne snoop around Mr. K's house.

Go for the Gold Watch

Ryan starts gambling again to get over his breakup with Simone; Anne meets a beautiful woman; Lauren saves Ryan from himself.

Double Down

Simone asks Ryan to stop wearing his wedding ring; Ryan has an encounter with his friend Hughie, a sad bachelor; Anne reluctantly lets Mr. K baby-sit her kids.

Ring and a Miss

When Ryan walks out during a live commercial, he is replaced by his new temporary assistant, Terrell Owens; Lauren is upset over a low group-evaluation score; Simone asks Ryan to come to a meditation center.

Go Deep

Ryan continues to pursue Simone despite Lauren's warning against dating group members; Yolanda, Anne, Sonia and Fausta use Owen as a body double when they decide to buy Lauren a wedding dress.

Pass Interference

Simone (Piper Perabo), a former member of the group, tries to force the other members to choose between her and Ryan; Anne helps Danny navigate his divorce.

Comeback Player of the Year

Despite Carrie's warning, Ryan asks her flaky friend on a date but faces competition from snowboarder Shaun White; Yolanda gets a job at the hospital where Sonia works.

Gooooaaaallll Doll!

Bob Costas asks Ryan to be a part of his new TV show; Anne is snubbed by Fausta; Mr. K looks for a new way to make a difference.

Win at All Costas

The support group's holiday party falls on the day that Mr. K expects the apocalypse to occur; Ryan asks Anne to join him and Steve on a trip to wine country; Lauren fears her boyfriend is going to propose.

The World Ain't Over 'Til It's Over

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Recent widower Ryan King joins a grief counseling group at the behest of his employer.

S1 E20 | Matchup Problems