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.

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.

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.

Ryan hallucinates seeing his dead wife Janie. He takes it as a sign that he has to take of himself. Steven has broken up with Ashley, so he and Ryan go out on the town. In group, Lauren tells the group she has to pass her real estate exam.

It is Ryan's birthday and he does not want to celebrate. Janie used to make a big production, planning months in advance, and he just wants a quiet night. The group plans a big celebration for him. It turns out to be a great night for all.

Lauren announces that Yolanda is graduating from therapy and will have a celebration party. Yolanda realizes she is not ready to leave after all. Meanwhile, Ryan takes Own under his wings as a big brother and helps towards his healing.

An old friend of Ryan and Steven's from college comes to town. Steven wants to date Amy and wants clearance from Ryan. Ryan is OK with this-until he actually sees Amy again. Ryan hosts Thanksgiving dinner for them and the group.

Ryan is ready to date again and updates his Facebook status to available. An Olympic beach volleyball winner invites him to meet her friends. It does not work out. Danny helps Sonia find her cat. George celebrates another year of life.

Mr K is ready for the end of the world when the Mayan calendar ends. He hosts a holiday/world end party. Since Anne is always grieving, Ryan invites her along to the annual trip to the wine country with Steven. Lauren's boyfriend proposes.

Ryan misses the girl stuff he used to do with his wife, so he & Carrie become girlfriends. Ryan decides he is ready to date and asks Carrie's friend. Yolanda gets a job at the hospital but sabotages her own job by acting like a party girl.

Simone, a former group member, returns to the group. Everyone is enthused because they all love her. Ryan is afraid she will change the group dynamics. Steven wants to teach Ryan a lesson and enlists the aid of Mr K and Terrell Owens.

Ryan tries to continue a relationship with Simone but he keeps seeing Janie's ghost which prohibits him from moving forward. The women in the group want to wedding dress shop for Lauren, but she is not ready for it.

Ryan does not want to be alone again after Simone left. Fausta takes him with her to bingo, and then Ryan's gambling habit kicks in. Soon he turns everything into a bet so he can gamble. A woman makes a pass at Anne.

Ryan's radio show is Number 1. Ryan thinks he should be happy. Lauren tells him happiness can come from helping others, not winning awards. Ryan decides to help Danny how to act with women. Anne and Owen want to know more about Mr K.

Anne sets Ryan up with a friend of hers that is recently widowed. Anne goes with them on the meet-and-greet date. Talya seems to flirt with both of them. Yolanda is forced by her parents to go on a cruise to meet single men.

Lauren is full of energy to move on after her breakup Wyatt. This inspires the group to move on in their own lives until they realize they are not ready. Lauren thinks she has failed the group. Her advice to Ryan proves she has not failed.