A girl plays Cupid for her mom, but has to invent the right man to woo her in this romantic comedy. Jean Hamilton (Heather Locklear) is a single mother with two daughters, teenaged Holly (Hilary Duff) and grade-school-aged Zoe (Aria Wallace). Fortysomething Jean has stumbled in and out of a number of bad relationships in her lifetime, and is desperate to find a good man; however, Holly has grown a bit tired of Jean's favored means of therapy after a bad breakup -- packing up the family and moving to a new city. Once Jean and her girls settle in Brooklyn, Holly thinks they should stay for a while, and when Jean's romantic prospects begin to look less than rosy, Holly and her new friend Amy (Vanessa Lengies) decide to invent a secret admirer for her. Needing advice on what the "perfect man" would say and do, Holly and Amy turn to Ben (Chris Noth), Amy's uncle who talks a very good game when it comes to romance. But convincing Jean that there's a real man behind the steady stream of letters and e-mails from her new admirer isn't as easy as Holly imagines, and it looks as if her imaginary suitor might get in the way of a flesh-and-blood Mr. Right.