David (Jerry O'Connell) is informed by his girlfriend of five years Sarah (Bridgette L. Wilson) that she is leaving for New York for two months in order for him to decide whether he is ready to marry her. Seeking advice from his wacky, womanising best friends (Ryan Reynolds and Bill Bellamy,) David begins to navigate the treacherous Los Angeles singles scene until fate intervenes and he falls for a mystery woman! Sarah meanwhile gets an offer from her handsome boss (You Can Count On Me's Jon Tenney) that she may not be able to refuse. David's search for what he thinks might be his true love triggers memories of a girl from his past that figures into the lives of all the characters, with some wildly unexpected results!
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