St. Valentine's Day delivers a few surprises for the Camden family. A grounded Simon is asked out by a senior. Annie's attempt to surprise Eric with romantic Valentine's plans backfires and results in a big fight. Mary discovers Robbie's plans with Joy. Lucy and Mary learn that Jeremy and Wilson both have dates for Valentine's. Matt seeks his fathers help as he wants to settle down, which leads him to seek out old girlfriends as to why they're no longer together. Ruthie is hesitant to go to a party because her friend tricked her into asking out a boy she's already going out with.

Kevin is now living in the garage apartment and is madly in love with Lucy and waiting for the right time to ask Lucy to marry him. He invites his new rookie partner Roxanne over to meet Lucy who takes one look at her and flies into a jealous frenzy. Robbie is jealous of Kevin because he feels as though Kevin is like a new big brother taking over Matt's place. Robbie, who has been lamenting the departure of girlfriend Joy, may also be ready for romance when he runs into Kevin's partner Roxanne, an old classmate from 7th grade.

Ruthie is asked to babysit a chimp which lives across the street. Ruthie also invites her boyfriend over which stuns Eric. Mary desperately tries to keep her mysterious new boyfriend a secret. When he unexpectedly shows up at the Camden home, no one is more surprised than Eric to see the good-looking 40-something pilot standing in the doorway.

Ken Smith pays a visit to Eric and Annie to accuse Mary of seducing his son. He threatens to sell the land next to the church if Mary doesn't break up with Jack. Simon finds out from Cecilla that a girl from his dating service is pregnant. Simon turns to her to try to help her. He convinces her to drop her baby off at a hospital where the baby can go for safe keeping. Lucy wonders if Kevin has ever been with another women after she catches Ben reading her journal. When Ben picks Ruthie up from school, he see's a girl making fun of her and then she makes fun of him, which leads to the vice principal calling the police.

Eric and Rabbi Glass pay a visit to the church to spy on the new associate pastor. Meanwhile, Ruthie is in big trouble when she's caught slow dancing with her boyfriend when she's supposed to be babysitting Sam and David. Meanwhile, Lucy asks Simon to dig up some information on Roxanne during his ride-along with her and Kevin in their patrol car. Lastly, Kevin has some explaining to do to Lucy after he runs into his ex-wife.

In the midst of a career crisis and much to Annie's dismay, Eric takes a job as a talk DJ at a college radio station, but things become serious fast when Eric and his producer find themselves counseling a male student who calls in threatening suicide during his first shift. Lucy refuses to spend time with Roxanne which puts Kevin in an impossible situation. Later on, Roxanne asks her boss to assign her a new partner as tensions simmer between her and Lucy. Ben is almost arrested when he accompanies Simon and Cecilia to an underage club. Ruthie tries to figure out a way to breakup with her boyfriend without making him cry.