Three single men look for love in Chicago with help from a female life coach. The trio have been friends since childhood and all have different problems with women. Tim's girlfriends always dump him; Doug can't get over his ex-wife; and Kyle is a Casanova-type who fears no one really wants him. Tim gets no help from his dad, Tug, an ex-NFLer, but his sister Molly advises him to seek advice from Dr. Victoria Stangel, a famous---and gorgeous---life coach.