Dating is never easy. Early in the search for love, people find the golden formula for meeting a soul mate is one part humiliation, two parts aggravation, and a little blind luck thrown in for the fortunate. Today's dating game is a blur of websites, speed lunches and hordes of friends and relatives who know just the wrong person for you.
Thirty-something pre-school teacher Sarah Nolan (Diane Lane) has been divorced for eight months, which is much too long for her co-workers and family to bear. With the best of intentions and only her happiness in mind, Sarah's sisters, Carol (Elizabeth Perkins) and Christine (Ali Hillis), begin lining up less-than-savory potential suitors. Meanwhile, their widowed father, Bill (Christopher Plummer), is way ahead of the curve, having already cornered the market on internet dates, including his new web squeeze, the free-spirited Dolly (Stockard Channing).
Eager to launch her sister's cyber-dating debut, Carol pretends to be Sarah, goes online and puts her profile on perfectmatch.com, with the last line being "Must love dogs." Sarah soon endures a torrent of eager wannabes and one very possible maybe, the handsome and accomplished but surprisingly awkward web date Jake (John Cusack) as well as Bob (Dermot Mulroney), the newly-divorced dad of one of her students, a hot prospect who may prove too good to be true.
As she braves a series of hilariously disastrous mismatches and first dates, Sarah begins to trust her own instincts again and learns that, no matter what, it's never a good idea to give up on love.
Based on the best-selling book by Claire Cook.