
Double Down
Ryan, still pained from the breakup with Simone, backslides into his old gambling habit, though sternly warned by Lauren to steer clear. But when he receives the life insurance check for his deceased wife, it’s more than he can bear and he starts making bets on anything and everything. Meanwhile Anne meets a stunning, young bookstore clerk, Brittney, who turns out to be all beauty and no brains.
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More from this season

S1 E1
Pilot
Ryan King, a radio sports personality, returns to work after grieving for his wife's recent death. His boss says he is not ready to return to work and must attend counseling. He reluctantly attends and meets others who also have to move on.

S1 E2
He Got Game, She Got Cats
Ryan does not like to be alone in his house. At group, Ryan encourages Sonia to break up with her boyfriend. She does, but then becomes the cat lady. Ryan has to deal with the fallout. Also, Ryan helps George replace a lost basketball.

S1 E3
There's No 'Ryan' in Team
Ryan does not want to tell his landscaper his wife has died, but the group convinces him he has to do it. The landscaper builds a shrine to Jannie. Meanwhile, the group thinks Ryan does not like to be seen with them outside the meetings.

S1 E4
Bench-Clearing Brawl
Ryan is invited to play a pick-up hockey game with Jeremy Roenick. Later, Ryan finds out it was a setup sympathy invitation. In Group, Lauren has everyone make a collage to express their feelings. Ryan attends a lesbian wedding with Anne.