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.

Despite Lauren's warning to Ryan of no dating among group members, he continues to pursue Simone but each time things heat-up with them, Janie's ghost appears, throwing Ryan off his game. The group helps Ryan deal with the guilt he feels as he starts dating again. Meanwhile Anne, Yolanda, Sonia, and Fausta decide to buy Lauren a wedding dress and use Owen as a body double.