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.

Pat refuses to accept Ken's diagnosis that his stressful relationship with girlfriend Megan is causing his mysterious rash. Meanwhile, Dave wonders how he can break up with Emily without hurting her feelings, and Clark invites Allison to a new meditation studio.

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.

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

Ken finds out about Clark and Connor's surprise wedding and is tasked with getting the guests there.

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.

Allison finds a suspicious lump in her breast during a self-check leading Ken and the HMO group to rush to her side as she awaits the results of the doctor's tests anxiously; Dave tries to figure out how he will portray a character in the play.

Pat eyes a promotion and asks Ken to put a good word in for him with the CEO of Welltopia.

Ken's dream comes true when he's cast in a comedy series that takes place at a community college.

Ken is stressed out at work over his “whining, complaining” patients so he needs a therapy session with Allison. Back at home, Ken is nervous about Molly’s driving test – “What if she doesn’t fail!”

Pat wants everyone to start working on Saturdays, so the workers in the office ask Ken to talk Pat out of it. When Ken visits Pat at home, he's shocked to find out he's living in a boat in the driveway. After Pat explains he's going through a divorce but still loves his wife, Ken thinks they've had a bonding moment. Meanwhile, Dave is given a new nickname at school and it brings up bad memories for Allison.

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.

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.

Ken's confidence as a medical expert witness is shattered when the plaintiff's lawyer shreds his credibility on the stand; Dave gets Allison's help to sew a designer dress for Molly.

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

When the office celebrates a promotion for Clark, Ken is oblivious since he lives in his own world…it’s the last straw for Clark dealing with Ken’s selfish ways. Clark writes a fake complaint comment card about Ken, so he’s forced to attend a training seminar for better bedside manners, which leaves Allison at home to have dinner with Ken’s parents.

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.

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.

When Allison gushes about how excited she is to go to Hawaii for the holidays, Ken realizes that he forgot to ask for those days off. So Ken, not wanting to admit he messed up, turns to lying, begging and bribing the master scheduler for the office (with whom no one has ever met), hoping he can give him the time off.

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.

Allison is upset to find out that Ken hasn't had a physical in years and urges him to do so. Ken asks Julie to sign that he's had a physical, but Julie insists on doing the real thing due to her professionalism. After the physical, Julie learns that Ken is suffering from moments of high stress - he blames Allison at first, but then they both realize it's due to their kids and their growing concerns. Meanwhile, Molly is having trouble holding down a job to earn money to go to skiing, but uses her entrepreneurial spirit to make the den's bathroom available to a nearby film crew - much to her parents' dismay.

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 feels that Molly is pulling away as a teenager and tries to reconnect by taking her and her friends to a concert for Emblem3. Though she is embarrassed by her dad’s antics at the concert, Molly does appreciate the effort and finally warms up to her dad — just a little. Meanwhile, Allison takes Dave to a birthday party, but after he cuts his foot, he wreaks havoc on the Welltopia team when he is forced to face a big fear – a needle for the tetanus shot. Also, Damona struggles with how to break things off with Pat.

Molly rebels and gets a Japanese tattoo, which spirals Ken and Allison into having a cultural face-off. At a holiday dinner, they push their traditional dishes on their guests, while Dave documents the Thanksgiving events for a school project. Julie invites the office over to her place – but Damona and Clark try finding a way to leave early so they can make it to their other Thanksgiving plans.

When Molly brings home her boyfriend, Allison has a conflict of interest when she realizes that he’s the son of one of her patients. Through a therapy session, Allison concludes that Molly’s boyfriend is cheating on her, but when Ken and Allison try to pry it out of him, it’s actually Molly who admits to cheating. This leads Allison to reveal her own overlapping romance when she first started dating Ken. Meanwhile, Pat begins kissing up to the staff, knowing that his evaluation is coming up.