Mia and Casey offer to give Maddie a Halloween-free party for her birthday, which falls on the same day as the holiday; Mia finds a mysterious videotape among Casey's things.

Casey has big plans for his first Valentine's Day with Mia. But Ben and Joel tell him that their rule is to never buy expensive Valentine's Day gifts for their ladies because doing so would set a costly precedent. Casey goes ahead with his plans anyway, and Ben realizes that he too wants to show Maddie how he feels. When Joel finds out, he decides to compete with them no matter the cost - and gets singer/pianist Michael Feinstein to perform.

Casey's ex-girlfriend wants the couch she loaned him when they were still together; Maddie updates Vicky and Joel's wills.