The gang rallies around Sid to help him through his commitment issues to new beau John. Meanwhile, Margaret attempts to conquer her fear of flying by volunteering at the airport.

As Hank and Margaret mentor an awkward high school student and help him decide on whether or not to go to the prom, Hank is forced to face a traumatic event that happened to him in high school. Meanwhile, Sid's boyfriend invites him to tour the wine country on bicycles, but Sid is mortified because he doesn't know how to ride a bike.