Shawn Griffin and Rachel Cooper have been best friends practically since birth, thanks to their families' close relationship. But for the past few years, Shawn has been fantasizing about getting his best pal in his bed. When she announces she's taking a trip to reconnect with an old lover, Shawn knows the time has come to put up or shut up. If she wants to go to New York City, fine. But he's coming with her. Rachel doesn't know what to think of Shawn's sudden interest. Determined to live life on her own terms, she refuses to fall right in line with her wealthy family's wish that they get married and have perfect little babies. She just didn't count on how determined her seemingly laid back -- and extremely sexy -- best friend would become after setting his sights on what he wants. Her, over and over again.