Nikki’s a sexual grifter, a fun-loving, freeloading hipster who uses his looks and sexual prowess to charm his way into the hearts of the city’s richest women and enjoy their lifestyle. That’s how he gets free places to live, fantastic gifts, A-list access, and plenty of sex. The women get to feel young, beautiful and utterly fulfilled in the bedroom.

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 Heather, a gorgeous waitress his own age. She comes to visit Nikki at Samantha’s house while Samantha is out of town and believes the incredible place to be his. Unbeknownst to Nikki, Heather lives by playing the same game.

When Samantha returns, she discovers Nikki’s infidelity and he’s put out on the street. With nowhere else to turn, he 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-upmanship, each shows the other their best grifts, and they unexpectedly begin falling in love. Soon, the truth of their unfolding relationship forces a choice between love and money …