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.

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.

Molly admits to taking a sip of beer at a party, but insists she hated it and didn't drink the rest. While Allison is happy Molly is being honest with them, Ken is afraid of losing his little girl and uses the opportunity to explain to her what alcohol does to the body... in medical terms. His experiment goes awry when he accidentally gets blitzed and makes a fool of himself in front of her friends.

Ken's sister Wendi, a successful doctor/TV host on a medical talk show, comes to visit the family and tension ensues. Ken can't admit that he's jealous of his sister's newfound success. So when Wendi invites Ken to be a guest on her show, he makes a mockery of it.

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.

Ken continues to push basketball (his passion sport) on Dave, but his son is more interested in going to a city council meeting about the extreme drought in California rather than playing in a game. Meanwhile, Damona tries to work the system at the office to get more vacation days and Molly tries to convince her mom to let her wear a skimpy outfit.

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.

After Ken's father shows up unexpectedly, he takes care of chores around the house that Ken has not been doing.

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.

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.

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.

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.

Dave gets an impromptu birds-and-the-bees talk from Julie after Ken has been avoiding it, but he's not off the hook with Allison when she learns he took full credit. Meanwhile, Clark gets dubious advice from Pat.

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.