Valentine's Day delivers a few surprises for the Camden family as a grounded Simon is asked out by a senior, named 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 to meet with 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 are no longer together. Lastly, Ruthie is hesitant to go to a party because her friend tricked her into asking out a boy that she is already going out with.

After a love night, Matt has got married with rabbi Glass's daughter Sarah. Robbie is mildly amused at the fuzz of all other Camdens speculating and worrying whether Matt 'was dumber than Mary with Wilson'. Only Ruthie finds out, answering when Matt calls, but is sworn to secrecy. Meanwhile Matt and Sarah go tell her parents first, but she shies away from telling the truth and pretends they just got engaged, a lie they now have to extend to the Camden home, where the 'news' only adds to the mounting stress.