James Thomas Jackson is a player by definition. After the downfall of his first true relationship, he spends the next ten years playing the field. But when he's proposed to by Anesia Hawkins, he decides he's ready to give up his high speed lifestyle. At least that's what he thinks up until their wedding day when the Reverend asks if he will be committed to Anesia "'til death do you part?" Anesia Hawkins is young, beautiful, wealthy - and a born again virgin. When JT walks out on her on their wedding day naturally she's devastated. Unable to live in the same city with JT if she cannot be with him, she packs and creates a new life in New York. But with all the women involved in JT's life and all the advances Anesia is making in hers, they cannot stop wondering, "what if?" When Anesia's mother falls ill, a good relationship goes sour, a possible baby on the way and a little bit of spiritual cleansing is put into effect, the two may finally have their chance.