Sarah Nolan (DIANE LANE) is a pre-school teacher who's reluctantly reentering the world of dating following her divorce eight months ago. In fact, she's so bad at it that her family -- including sisters Carol (ELIZABETH PERKINS)and Christine (ALI HILLIS), as well as their widowed father Bill (CHRISTOPHER PLUMMER) -- have gathered for a family intervention of sorts where they hope to get her back on track. For Sarah, the only successful couple she currently knows is that of her gay coworker Leo (BRAD WILLIAM HENKE) and his significant other Eric (VICTOR WEBSTER), and her only real prospect, Bob Connor (DERMOT MULRONEY), is off limits to her since he's the father of one of her students.
Unbeknownst to Sarah, Carol has submitted her sister's gussied up profile to an online dating service, resulting in a bunch of losers that only further discourage Sarah about the dating process. One, however, has piqued her interest, although Jake (JOHN CUSACK) -- an over analytical and self-conscious boat builder -- turns out to have closet skeletons of his own in the form of dating issues.
It doesn't help that Sarah's brother Michael (GLENN HOWERTON) is having marital problems, or that their dad is playing the dating game like a Major Leaguer, seeing a bevy of women including Dolly (STOCKARD CHANNING) who eventually forms a bond with Sarah over what they see as an unfair dating process for older women. With her sisters pushing her to succeed, and his lawyer friend Charlie (BEN SHENKMAN) encouraging him to get back into the dating world and in bed with as many women as possible, Sarah and Jake tentatively start dating, unsure of whether they're right for each other.