Doug Brown desperately wants to ask out the secretary, Joanna, at his office, Sweaters Fur You, but does not have the courage to do so. On his way home from work he meets Clark, a homeless man, who previously was a master pick-up artist. The two form a deal that Clark will teach Doug how to pick-up girls and ultimately ask out Joanna for a fee. Clark teaches Doug how to pick-up girls and comedy ensues.