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Larry Walker, a successful advertising associate wants to give up his playboy ways and settle down with a former college girlfriend and current co-worker Monica James. There are just two problems; Monica doesn't think he can handle a serious relationship so she gives him one day to prove he is ready and now every women at the office seems to want Larry. With help from his best friend Jason, Larry has to negotiate the biggest deal of his career and find true love by the end of day.