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A woman finds herself drafted into the battle of finding the perfect man in this romantic comedy. Sarah Nolan (Diane Lane) is a kindergarten teacher in her mid-thirties who is still dealing with the emotional aftermath of her divorce eight months ago. While her sisters, Christine (Ali Hillis) and Carol (Elizabeth Perkins), both think Sarah needs to start dating again, Sarah herself isn't so sure. Carol decides to force the issue by posting Sarah's photo and profile on an Internet dating site, and soon a number of seemingly eligible bachelors are sending her e-mails in hopes of a date. However, nearly every man she meets turns out to be a loser, with the exception of Jake (John Cusack), who is smart, good looking, and even brings along a dog for their walk in the park (though he doesn't tell her the pooch was borrowed for the occasion). However, Sarah also makes the acquaintance of Bob (Dermot Mulroney), the divorced father of one of her students, and she finds herself having to choose