St. Valentine's Day delivers a few surprises for the Camden family as a grounded Simon is asked out by a senior, Maria. Annie's attempt to surprise Eric with romantic Valentine's plans backfires and results in a big fight. Meanwhile, a nosy Mary discovers Robbie's plans with Joy. Lucy runs into her ex-fiance Jeremy outside one of her classrooms and finds out that he is going to the pool hall and meeting a "friend" for Valentine's, which is to Lucy's surprise. Mary also meets up with Wilson who also has a new girlfriend, her old friend, Corey Conway. Also, Matt seeks his fathers help with his love life and wants to get serious with a girl, which leads him to seek out old girlfriends as to why they're no longer together. Lastly, Ruthie is hesitant to go to a party because her friend tricked her into asking out a boy she's already going out with.