 Josh (Anthony Michael Hall) is one of those guys who can t navigate the shallow NY singles scene. Not to worry, his two friends Tim (Lord Jamar) and Sean (Ivan Martin) are self proclaimed singles experts who are willing to help their buddy. From bestowing their dating wisdom, to giving their friend a total image make-over these two stop at nothing - including the writing, placement, and interviewing of a personal ad. Weeding out the three "right ones" or at least what they deem the most appropriate proves to be a monumental experience, even for these two. In the meantime, Josh applies some of his newly acquired wisdom coupled with his own honest approach on Doreen (Marlo Marron) - a woman his two buddies have deemed out of his league. Indeed, it appears that all of his advances go unnoticed on this lovely but embittered singled mom. Of course love does triumph in the end, but it is found by the heart and only after the age-old adage of "to thine own self be true" is learned by one and all.