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.
When Vanessa is featured in a local magazine article about entrepreneurs under 40 years old, a jealous Kevin tries to get attention for himself by securing his own award, while reminding her that she is over 40. Also, Chale fixes up Kyle on a date with his wild Aunt Kristin (Joell Weil).
After Kevin and Vanessa witness Kyle's success using a dating app that requires a close friend to choose one's perfect match, they agree to be each other's wingman and try their hand at matchmaking.
Vanessa convinces Kevin to go on a TV talk show with the "baby boy" he helped deliver years ago as a police officer; Kevin runs into his archnemesis, Frank Munson, at the appearance.
Vanessa is turning 47 and insists she doesn't want a party. After Kevin devises a elaborate plan to surprise her with a big bash, things begin to go wrong.
Kevin hires a personal assistant and Rootger protests so a competition is held. In that, Kevin loses track of Vanessa's assignment to provide security at a parking lot for Alviti, their big new client. Chale seeks financing to buy Enzo's.
Kendra and Chale rejects Kevin's offer to fund their purchase of Enzo's so Kevin puts them out. Kevin posts photos online of he, Sara and Jack having fun so Kendra returns in kind which helps Kevin figure out they are staying at Vanessa's.
Adam Sandler and Chris Rock guest star as Kevin's old bandmates as they try to reunite "Smokefish." It turns out that the band changed the course of Vanessa's life. Michael DelGuidice, who plays the keyboardist, wrote the theme song for the series, "Ordinary Guy."
