Jacey Lange has everything she has ever wanted. She is newly engaged, and her menswear line is one of the fastest-growing in the country. Beautiful, successful, and deeply in love, Jacey feels like she's on top of the world. That is, until she catches her fiance in bed with her assistant. Everything around her comes crashing down. Thankfully, her best friend, Leon, welcomes her back to her old apartment with open arms. The people in Jacey’s life watch for months as she wallows in her misery, until Leon hatches a plan: if Jacey agrees to get herself back out there and promises to go out with the next five guys that ask her, no matter who they are, then not only will he give her the master bedroom in the apartment, but both Leon and Jacey’s sister, Elise, will agree to stop meddling in her love life. In rapid succession, Jacey finds herself falling for five completely different men. Yet despite all their differences, there is something oddly familiar about each one. When she finds out why, it won't just change the way she feels about love, it will make her question everything she once thought was real.