Ken is stressed out at work over his "whining, complaining" patients so he needs a therapy session with Allison; while back at home, Ken is nervous about Molly's driving test - "What if she doesn't fail!".
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.
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 when Allison claims she is more Japanese than Ken is Korean. At a holiday dinner, they push their traditional dishes on their guests, while Dave documents the Thanksgiving events for a school project. Also, Julie, fearful of being alone due to a recent heartbreak, 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 dad arrives for an impromptu stay, he starts taking on chores that Ken hasn't gotten around to doing - like buying and installing a much needed new dishwasher, but then Ken purposefully breaks it. Meanwhile, Damona and Pat hook-up after a drunken night together. But instead of clinging to Damona the next day, Pat makes an announcement that takes Damona by complete surprise.
After Ken helps Dave in asking a girl he likes to go with him to the Valentine's Day dance, the plan quickly goes awry when Ken finds out that her dad is the well-known and rich malpractice lawyer whom he's had issues with in the past. Can these two "adults" put aside their dislike of each other for the good of their kids? Meanwhile, Julie changes her Valentine's Day party into a Presidents' Day party to cover up her rejection from Topher. So when Topher suddenly shows up, Damona and Clark provide their support.
Ken and the office staff are invited to a colleagues wedding, but things don't go as smoothly as they'd all like. Allison shows her dislike for weddings, but it turns out she just really doesn't like Ken's dancing - he's selfish on the floor. Meanwhile back at home, Molly hires someone to babysit Dave, but Dave wants to sneak out so he hires a friend to impersonate him. Also in the episode, Damona, Julie and Clark attend the wrong wedding, but Clark meets his dream guy there.
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.
When Ken is invited to be a medical expert witness at a trial, his confidence level, normally quite high, goes through the roof. However, when the plaintiff's lawyer hammers him and shreds his credibility on the stand, Ken's confidence as a doctor wavers. But, with the help of the HMO staff, Ken regains his swag, both in and out of the court room. Meanwhile at home, Allison helps Dave sew a replica designer dress for Molly, in the hopes of winning her respect and appreciation.
When Ken avoids giving Dave "the talk", Julie inadvertently does it herself. But then Ken has to fix things when Allison finds out that he took credit for doing it. Meanwhile, Clark takes questionable 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.