Deidra Parker is a plus size executive assistant, who has led a boring life and she's tired of it. So she decided to add some excitment to her life. Starting with getting the attention of the only man she has ever loved since they were kids in the sandbox and who also happened to be her boss, Jackson Reynolds. Jackson has the reputation of being a playboy, because his relationships never last longer than a month or two. Just ending his last relationship, Jackson starts to rethink his idea on dating and wants to give up on dating for a while. Will Deidra's new look and attitude make Jackson want to be in a lasting relationship or will he revert back to his old ways and hurt Deidra in the process?