Nikki isn't a gigolo. He's a sexual grifter, a fun-loving, freeloading hipster who understands his greatest assets are his looks and sexual prowess, which he uses to charm his way into the hearts of the city's richest women and enjoy their lifestyle. Nikki's latest conquest is Samantha, a stunning middle-aged lawyer who gives him more than he's ever had before. But, then he meets a gorgeous waitress his own age named Heather. She comes to visit Nikki at Samantha's house while Samantha is out of town, sees what an incredible place it is, and comes to the mistaken conclusion it's his. Unbeknownst to Nikki, Heather lives by playing the same game. When Samantha comes home, she discovers Nikki's infidelity and puts him out on the street. With nowhere else to turn, Nikki pulls out all the stops to win Heather over and they begin to form their own kind of bond. Sexually charged by a game of one-upsmanship, each shows the other their best grifts, and they unexpectedly begin falling in love - the one thing they can't do in the life they lead. Soon, the truth of their unfolding relationship forces a choice between love and money, and Nikki has to decide whether he can live on his own once and for all in the hopes of finding something real.