Single mother Jean (Heather Locklear) relocates every time she gets her heart broken by another guy, much to the dismay of her teenage daughter, Holly (Hilary Duff). Holly devises a plan to invent a secret admirer for her mother, so she'll be happy and not have to relocate anymore. Holly overhears her friend Amy's (Vanessa Lengies) uncle Ben (Chris Noth) ordering flowers for a woman, and decides to use his advice on women (which she acquires by telling him she needs help for a school project on romance). Following Ben's advice, she sends her mother orchids and other gifts and love notes, and is soon communicating with her mother as this fictitious admirer (who Holly names Ben) via the internet. As her mother becomes more interested, Holly has to find a photo of this admirer. She sends one of the real Ben, and then devises a reason why they can't meet in person, claiming he is working in China. While she is developing the online romance between her mother and fake Ben, and preventing her mother and the real Ben from meeting in person, she finds herself drawn to a cute, artistic boy in her class, Adam (Ben Feldman), but is unwilling to get close to anyone due to her history of being uprooted and having to say goodbye so often.