Tripp (McConaughey) es un atractivo soltero que, a sus 35 años, todavía vive con sus padres (Kathy Bates y Terry Bradshaw). Hartos de la situación, éstos deciden contratar los servicios de una joven motivadora profesional (Sarah Jessica Parker) que debe convencerlo de que ya es hora de que se independice.
Historia de dos parejas de Nueva York. Una es actriz de éxito y está casada con un hombre que, además de no trabajar, es adicto al sexo. El hermano de la actriz es también un vago que sale con una aspirante a novelista.
Skirt-chasing Gaul Alfred and comely American tourist Alice meet by chance and strike up a rapport during her whirlwind vacation in the City of Lights. Alas, Alice is soon jetting back over the Atlantic, which leaves the smitten Alfred hopelessly bereft, heartbroken, and determined to win her back. In a fit of desperation, he books a flight and follows in hot pursuit, settling in the Big Apple; his decision to set foot on a plane, however, represents the first of many disasters to befall him. In the course of Alfred's trip, the airline loses his luggage, and when he finally reaches Alice's doorstep, she isn't dazzled to see him but instead rather disgusted - she doesn't hesitate to tell him to beat it. Never one to relent, the ever-persistent Alfred grows convinced that she will eventually buckle, and decides to settle in Manhattan until that moment arrives and takes a job as a dog-sitter for the seedy businessman Farrakhan.
