Teenager Holly Hamilton is tired of moving every time her single mom Jean has another personal meltdown involving yet another second-rate guy. To distract her mother from her latest bad choice, Holly conceives the perfect plan for the perfect man.. an imaginary secret admirer who will romance Jean and boost her shaky self-esteem. When the virtual relationship takes off, Holly finds herself having to produce the suitor, borrowing her friend's charming and handsome Uncle Ben as the face behind the e-mails, notes and gifts. Holly must resort to increasingly desperate measures to keep the ruse alive and protect her mom's newfound happiness, almost missing the real perfect man when he does come along.

It's 1914 in New York City. Adult brother and sister Trippy Trellis and Fanny Trellis, whose parents are now deceased, were once wealthy, but Trippy squandered away the family fortune, about which no one knows except their cousin George Trellis and their many creditors. Fanny and Trippy still put on the façade to the outside world that they have money. The beautiful Fanny can have any man that she wants to marry, but she sets her sights on Job Skeffington, the son of Russian-Jewish immigrants. Job's wealth was self-made in finance. They met as Trippy was once employed by Job in his brokerage house. Fanny and Job, who is now aware of the Trellis' financial straits, ultimately do get married, much to the consternation of Fanny's many suitors, but most specifically to Trippy, who knows the reason why Fanny married him. Job also realizes that Fanny does not love him...