He didn't need help, just a little magic.
Josh (Anthony Michael Hall, 16 Candles, The Dead Zone) is a street performer who's not having an easy time in the singles scene. Not to worry, however, as his friends Tim (Lord Jamar, Oz) and Sean (Ivan Martin, Hollywood Ending), a pair of womanizing playboys, are more than willing to bestow their accumulated wisdom on Josh. They begin with a total image overhaul, followed by the writing and placement of a personal ad. They then undertake the daunting task of selecting three women that they consider not out of Josh's league.
Meanwhile, Josh develops a friendship with Doreen (Marlo Marron, Mi Vida Loca), a working single mom with no time for most men - especially when they're like Tim and Sean! As the two grow closer, Josh begins to realize that he may have a few lessons to teach his more worldly friends.