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In the present, Chuck (Dane Cook) is a successful dentist in his thirties, and runs a dental practice in the same building as his best friend Stu's (Dan Fogler) plastic surgery business.
Chuck finds himself unable to tell his girlfriend, Carol (Chelan Simmons), that he loves her, and she breaks up with him while having sex on the beach.
In retaliation, Anisha places a curse on Chuck, so that every single woman he sleeps with will break up with him and marry the next man who asks her out.
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Following the break up, Stu and Chuck decide to attend the wedding of one of Chuck’s ex-girlfriends, Katie.
At Katie’s wedding, Chuck becomes enamored with Cam Wexler (Jessica Alba), a clumsy, yet attractive and friendly marine biologist.