After Kevin learns Chale took a job to buy Kendra an engagement ring, he decides to make good on his overdue promise to buy Donna a proper ring, but his plan backfires when he tries to surprise her.
As Kevin tries to charm his neighbor into giving him permission to cut down one of her trees, he becomes intimidated by her imposing son, Rutger and invites them over for a non-existent party.
Kevin learns that his childhood nemesis is trying to reserve the church for his daughter's marriage, and the date is the same day that Kendra, Kevin's daughter, wants to reserve it for her wedding.
Kevin and Chale get jobs working in the warehouse of an electronics store to pay for the wedding, but Kevin unleashes his competitive side when Chale gets promoted to the sales floor.
When Goody and Didi invite the Motts on a weekend getaway, Kevin and Donna are offended that they weren't asked to go, causing them to go online to find new couples to hang out with.
Kevin comes out of retirement to reprise his undercover assignment, with fellow cop Vanessa Cellucci, in an ongoing police investigation; Donna is up for a promotion, Kendra gets accepted into law school; Chale gets a lucrative new job.
Kevin and his partner attend a fraudulent dealer's weekend art show in Boston, causing Kevin to miss out on going to Mets Fantasy Camp with his buddies; Chale's dream job isn't what he expected; Donna mouths off to her boss.
Kendra and Chale must get married before Chale is deported; Kevin seeks Father Phillip to officiate the ceremony; Vanessa helps Kendra with the wedding plans.
Kendra, who is overwhelmed by Kevin's helicopter parenting, tricks him into taking a job with his old partner, Vanessa, who now operates her own private security company.
Kevin goes undercover to find out the truth when Vanessa suggests that Sara has a secret boyfriend. Meanwhile, Jack desperately searches for an illness he can claim as his own after the "cool" kids with peanut allergies learn he's been lying about sharing their malady.
Kevin steps in as Vanessa's "successful doctor" date at her sister's wedding, in an attempt to impress Vanessa's very judgmental father. Meanwhile, Kyle helps Kendra and Chale make a fake photo collage of honeymoon pictures to tout on social media.
Vanessa plots her revenge on Kevin after learning he lied his way out of working on a Sunday to attend a football game with Goody. Meanwhile, Kyle dates a new girlfriend; and Chale and Kendra have their first squabble as a couple.
Kevin and Chale set out on a road trip to retrieve an owl-shaped cookie jar that Kevin sold before realizing how much it meant to Kendra. Also, after Vanessa rejects Kyle's attempt to woo her, she and Kendra help get him back on the dating scene.
When Kevin and Vanessa try to land a security gig at a toy store, they get sidetracked practicing their new business pitch and wind up locked in the store after hours. Also, Chale is having success working at Enzo's.
Kevin and Vanessa fear Rootger plans to sue them for falling at their security firm's event. They solicit quasi-legal advice from law student Kendra at Enzo's and soon many others are buying a pizza slice that comes with law advice.
After Kevin insists he can handle cooking a full Thanksgiving dinner for his family and Vanessa, he realizes he's in over his head and secretly asks his flirtatious neighbor Wendy for help.
Kevin goes undercover as a janitor at a car dealership. When he accidentally sells a car to a customer, he tries to win salesman of the month. Meanwhile, Chale learns that Kendra used to be into ventriloquism.