The episode opens with a flashback to Ken's botched marriage proposal on Halloween. Now 20 years later, Ken tries to arrange the perfect re-proposal for Allison. Meanwhile at the office, which is decorated for Halloween, Damona and Julie accidentally drug Pat and then take advantage of their boss' suddenly giving mood.

The Park family are in the airport on their way home from Hawaii when their flight is delayed for several hours. Ken has an interaction with Dr. Oz that goes awry - and then needs to get the famous TV doctor to switch airplane seats with him. Meanwhile, Allison gets overly involved in Molly's love life and accidentally breaks up with her boyfriend via text message, and Dave finds himself in a high-stakes card game with some college students. Back at Welltopia, it's "Black Monday," the clinic's busiest day of the year, and in Ken's absence, Julie is the doctor in charge, and Clark and Damona have to help her learn that thoroughness doesn't have to take forever.

Dave's date to the Valentine's Day dance ends up being the daughter of a well-known, successful malpractice lawyer who does not like Ken. Julie feels rejected by Topher.

Things end up not running smoothly after Ken and the office staff attend a colleague's wedding. Molly hires a baby sitter for Dave. Dave attempts to sneak out and he hires a friend to impersonate him.

Ken, at the insistence of Allison, reluctantly joins a civics-minded community group – but it may not be what it seems.

A visit from Ken’s college friend, a touring stand-up comedian, ultimately spurs Ken to pursue his own lifelong dream of stand-up comedy. But when he does it, suddenly it’s not as easy as he thought, nor does it go as he planned.

Allison convinces a reluctant Ken that it would be a fun family adventure to drive to her parents for Thanksgiving dinner. But along the way, a traffic jam combined with her husband and kids’ antics causes her to lose her usual cool. Meanwhile, Clark takes charge to serve Thanksgiving dinner at a shelter for the homeless, but his bossiness and unnecessary attention to details drives everyone a little crazy.

When Ken wants to apologize to a patient for missing an important medical detail, Pat advises against it, and the situation gets out of hand. Meanwhile, D.K. shakes things up at Dave's parent/teacher conference.

When Ken's attractive new intern, Erin, shows up at Welltopia, Allison starts to feel a bit insecure when Erin's admiration for Ken veers into flirtatious territory. Meanwhile, Damona's boyfriend, Eric, wants her to confront her musical past when he learns she was the lead singer on the C & C Music Factory's 1990 dance jam, "Gonna Make You Sweat." Molly's first date with Jae leaves her wondering if he really likes her, so matchmaker D.K. goes on a secret mission to see what he can find out.

Ken spirals a bit out of control when he finds out Molly's new boyfriend, Jae, is leaving behind his pre-med studies to be an artist. At Welltopia, Pat asks Clark to monitor his weight loss program; and when Damona learns she isn't required to wear scrubs, her new look results in several awkward moments.

Amy, the producer of a documentary health series, follows Ken around to record a typical day at an HMO, giving Ken his big moment in the limelight. But much to Ken’s chagrin, a series of the less than thrilling day-to-day parts of the job at Welltopia leads Ken to doubt his own career choice.

When the star of Molly’s high school basketball team injures his ankle, Ken’s routine exam and unexpected diagnosis shocks everyone since it might keep the young man from playing in the big game. Meanwhile, Clark and Connor take another major step in their relationship before getting married, and Pat lets Allison in on the secret espresso coffeemaker he keeps in his office.

Ken lets Allison, who is second-guessing her decision to have a low-key Valentine’s Day, think that a love poem Dave wrote for his sweetheart, Emily, is meant for her. Meanwhile, Molly and Jae consider Valentine’s Day a corporate concoction; Clark plans a romantic scavenger hunt to lead Connor to his present; and complications arise when Damona and Eric have dinner at a restaurant that she and Pat once frequented when they were dating.