Nice guys finish last... or at least that's what they say. Boon, a lawyer from Chicago, is a hopeless romantic; however, life keeps dealing him a shady hand when it comes to the opposite sex. It seems as though every woman Boon finds interest in tears him down. CiCi, Boon's best friend and former high school sweetheart, tries to be there for him throughout his trials and tribulations, but she isn't quite over him herself. She remains in his corner as he hops from woman to woman, relationship to relationship, getting his heart broken. Gorgeous and intelligent, Amerie is also a lawyer from Chitown; Boon meets her and soon, the sparks fly. Boon falls head over heels and he soon begins to wonder if she is the one. However, the ultimate betrayal soon sends one of the lovebirds into a downward spiral. Pleasure in paradise turns into the highway to hell, emotions run rampant, and a distraught lover looks for reconciliation-however it can be acquired. Who said it was better to have loved and lost? After this tale of lost loves, infidelity, and the malevolence it brings about, they'll be forcefully inclined to rephrase that statement.