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Lauren struggles without Wyatt, and Ryan struggles to let go of Janie by spreading her ashes. The group rally to help them both.
Ryan finds a change of perspective from the inside of the K-BAL mascot suit. The girls of the group attend Lauren's bachelorette party, where Ryan ends up helping her make some tough decisions.
Anne sets up Ryan on a date with a hot widow she met at the graveyard. Yolanda is sent on an Asian Christian singles cruise by her parents, but finds that the guy she likes is attracted to someone else.
Ryan tries to help Danny and Sonia get together, meanwhile the others try to find out more about the mysterious Mr K.
Trying to get over Simone, Ryan takes to gambling, however gambling has been an addiction in his past, and soon becomes more of a problem than missing Simone.
Ryan struggles with the idea of taking off his wedding ring, but this may be the thing that defines his new relationship with Simone.
Terrell gets a temp job at K-BAL, Ryan, Simone and Mr. K go on a meditation retreat.
When Ryan starts dating Simone, Janie's ghost throws him off his game. The rest of the group uses Owen as a body double, after deciding to buy Lauren a wedding dress.
Simone is back! A previous group member returns and Ryan finds his spot in the group under threat, but as time goes by Ryan begins to see what everybody finds so special about Simone.
Despite Carrie's warning, Ryan wants to get his first date out of the way and asks Carrie's flaky friend, but not without a little competition from Shaun White. Meanwhile, Yolanda starts a new job at the hospital where Sonia works and tries to reinvent herself.
Bob Costas asks Ryan to join his new TV show. Meanwhile, Mr. K tries to make a difference in the group.
When the group settles on a date for their holiday party, it happens to fall on what Mr. K believes will be the end of the world. Ryan invites Anne along on his annual trip to wine country with Steven and Lauren worries her boyfriend is ready to pop the question.moreless
Ryan tries to ease back into the dating scene with the help of guest star Misty May-Treanor. Meanwhile, George outlives his life expectancy as set by doctors and decides to celebrate.
Amy (Lauren Graham), a college friend of Ryan and Steven, comes to visit and the two fight for her affections. Ryan decides to hold a Thanksgiving party at the office and invites the entire therapy group.
Ryan tries to take Owen under his wing.
The group plans a scavenger hunt for Ryan's birthday.
The group points out to Ryan that he is grief-eating, which he vehemently denies. Meanwhile, the group's monthly outing is a dinner at the same restaurant that Lauren and her boyfriend are dining. When he shares private information about the group, they demand that Lauren open up to them abut her life as they have to he.moreless
Ryan encounters the ghostly apparition of his dead wife; the group tries to help Lauren overcome her test anxiety so that she can pass her real estate exam.
Ryan is thrilled to finally be accepted on to former NHL star Jeremy Roenick's pick-up hockey team not realizing that both the invitation and his success in his first game is out sympathy for the loss of his wife. Meanwhile at the group, Ryan agrees to escort Ann to a wedding and struggles with having to put together a collage of his past and future.moreless
Steven helps Ryan overcome a loss.
Ryan is unsure if he should let the group into his "real life."
Following the death of his wife, a radio sport broadcaster attends a support group at the request of his employer.