After a former bandmate talks Kevin into reuniting with their old band, Smokefish, with hopes of making it big, Vanessa realizes a chance encounter with the band in her past changed the course of her life.

Kevin offers to help Kendra and Chale buy Enzo's, but they soon realize that the partnership won't work when Kevin's idea of a silent partner is not so silent. As the tension among them escalates, Kendra and Chale find peace at Vanessa's apartment.

When Monkey Fist lands Alviti's big account to provide security for his parking garages, Kevin inadvertently derails Rootger's efforts to study for his security guard test and puts the new job in jeopardy, much to Vanessa's dismay. Also, Kendra and Chale try to persuade an investor to help finance their brew pub idea.

Plans to knock down Enzo's and build a parking lot cause problems for the guys. But when Alviti makes them a lucrative job offer, the future of Enzo's is at stake.

Vanessa thinks she's friendless when none of her pals are available to go to dinner with her on her birthday. Feeling lonely while waiting for Kevin to pick her up for what she thinks is just a dinner for two, Vanessa gets tipsy with Kyle, and the two share a flirtatious moment.

Vanessa convinces Kevin to go on a TV talk show with the "baby boy" he helped deliver years ago as a cop, but her plan to promote Monkey Fist backfires when Kevin runs into his arch-nemesis, Frank Munson.

After convincing Kevin to break things off with his neighbor, Wendy, who had reeled him in with her delicious meals, Vanessa feels compelled to cook for him despite being culinarily challenged.

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.

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.

On a flight for a security job, Vanessa tells a flight attendant that she and Kevin are newly married in order to get bumped up to first class, but her fib creates a lot of extra baggage when Kevin meets Lisa and the two hit it off

Vanessa encourages Kevin to ask out a client, Rebecca, after she shows interest in him.

After Kevin and Vanessa nail a pitch for a new job for their security company, Monkey Fist, they run into Frank, the owner of a rival company who is determined to put them out of business by pitting Kevin and Vanessa against each other.

While Vanessa and the Gable family gather around the Christmas tree, Vanessa and Kevin reminisce about their first patrol together.

After Vanessa asks Kevin to help her get a date with a handsome personal trainer, Alejandro, she gets frustrated when Kevin starts training with him instead. Also, Chale reluctantly takes advice from Kyle when the health inspector stops by Enzo's.

As part of a security job, Kevin goes undercover as a janitor at a car dealership, but he accidentally sells a car to a customer and finds himself on track to win top salesman of the month. Also, Chale reveals his phobia of puppets after learning that Kendra used to be into ventriloquism.

After Kevin insists he can handle cooking a full Thanksgiving dinner for Vanessa and his family, he realizes he's in over his head and secretly asks his flirtatious neighbor, Wendy, for help.

Kevin and Vanessa concoct a plan when they fear Rootger might sue them after he slips and injures himself at their office. Also, Kendra dispenses legal advice at Enzo's for paying customers.

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 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.

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. Also, Kyle has a new girlfriend, Denise, and Chale and Kendra have their first squabble as a married couple.

After Vanessa's relationship with a hunky doctor goes bust before her sister's wedding, Kevin steps in as her 'successful doctor' date. Also, Kyle helps Kendra and Chale make a fake photo collage of honeymoon pictures to tout on social media

After Vanessa suggests that Sara has a secret boyfriend, Kevin goes undercover to find out the truth. Also, 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.

Overwhelmed by Kevin's helicopter parenting, Kendra tricks him into taking a job at Vanessa's new private security company.

To officiate the ceremony, Vanessa helps Kendra put together the last-minute affair.