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.
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.
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.
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.
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.
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.
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.
Lauren says she does not want to marry Wyatt and asks Ryan to help her break up with him. Meanwhile, Ryan gets a sexy call from a drunken Carrie and he asks Lauren to help with that situation. The group plans a bachelorette party for Lauren.