In the second season opener, Kendra and Chale must get married immediately when the Gables learn that he is about to be deported. As Kevin chases down Father Phillip to officiate the ceremony, Vanessa helps Kendra put together the last-minute affair.
Overwhelmed by Kevin's helicopter parenting, Kendra tricks him into taking a job at Vanessa's new private security company.
After Vanessa suggests that Sara has a secret boyfriend, Kevin goes undercover to find out the truth.
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
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 and Chale and Kendra have their first squabble as a married couple.
Kevin and Chale go on a road trip to retrieve a cookie jar that Kevin sold before realizing how much it meant to Kendra; Vanessa and Kendra try to help Kyle with dating.
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 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.
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 askes his flirtatious neighbor for help.
As part of a security job, Kevin goes undercover as a janitor at a car dealership. Also, Chale reveals his phobia of puppets after learning that Kendra used to be into ventriloquism.
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.
While Vanessa and the Gable family gather around the Christmas tree, Vanessa and Kevin reminisce about their first patrol together.
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.
Vanessa encourages Kevin to ask out a client after she shows interest in him.
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.
When Vanessa is featured in a local magazine article about entrepreneurs under 40 years old, a jealous Kevin tries to get attention for himself. Also, Chale fixes up Kyle on a date with his wild Aunt Kristin.
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.
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.
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, at the appearance.
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, she gets tipsy with Kyle.
Kevin and Vanessa devise a plan to save Enzo's restaurant after learning the new owner plans to knock it down; the owner makes them a lucrative job offer, which puts the future of the restaurant in peril.
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.
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.
