Ken is taken aback when he meets Allison’s former boyfriend Kevin O’Connell, now a very hot and successful doctor. So when Ken is asked to speak at a banquet honoring Kevin, he uses the opportunity more as a roast. Meanwhile, Molly struggles with a school assignment asking for what she wants to be when she grows up.

Ken is delighted when a long-time favorite patient/comedian comes in for a checkup. Unfortunately, tests reveal that Dicky’s cancer has come back and he must stay at the hospital, keeping him from performing what was going to be his last stand-up show. But Ken is determined to get Dicky what he wants! Meanwhile, Allison runs into an old-time patient at another therapist’s office, causing her to question her own abilities and friendship with the woman.

When Dave announces he’s been invited to pitch his Hot Legs Duvet invention on “Shark Tank,” Ken is excited. But then he gets nervous about throwing his son into the Tank when he realizes how tough the Sharks can be. Meanwhile, Molly heads to Welltopia to intern, and Pat is so impressed that he takes her under his wing.

Ken's old professor makes an appointment and torments Ken during his visit.