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.

The group celebrates Ryan's birthday with a scavenger hunt. Elsewhere, Sonia cares for Steven following his colonoscopy, and Mr. K and Anne connect over their love of musicals.

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.

Ryan woos an attractive group member, but Janie's ghost materializes as he feels great guilt for dating again. Elsewhere, some of the ladies set out to buy a wedding dress for Lauren.

Worried that his career is in shambles, Ryan travels to New York with Steven to interview as host of a national show, set up for him by Anne. Meanwhile, the group grumbles they're getting nothing out of their sessions and blame Lauren to such an extent that Yolanda and Sonia make up a big problem for her to fix. When both plans crash, the group finds renewed strength from their failures.