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.