Bob Costas asks Ryan to join him on a TV show he is hosting. Fausta invites everyone to her niece's 15th birthday party - except for Anne. Mr K's invention for a rocket trip to Mar's is claimed a success, but does not know his next project.
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.
Lauren hands out evaluation forms to her students; someone gives her a low grade and she struggles to find out who did it. Ryan hires Terrell Owens as an assistant while Carey is away. Ryan and Simone try to be the person the other one wants.
Simone wants Ryan to remove his wedding ring, but he finds he cannot. After Ryan visits with an old friend, he realizes he is ready to go forward with Simone. Anne hires Mr K for a babysitter one night, and he turns out to be a super-nanny.
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 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.
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.