Jenna Fisher, a 22-year-old kindergarten teacher has lived in Chicago her whole life, but when her past starts catching up to her, she has to make a decision and move all the way to New York. Because of her past Jenna lived her life based off on "what if's". Damien Maxwell, a 27-year-old billionaire and the owner of Maxwell Industry is a single father to his 4 year old son Jamie Maxwell. After the death of Jamie's mother, Damien vowed not to open up his heart again, but will the arrival of the new teacher stir up something in his closed-up heart. And with the unexpected arrival of Damien Maxwell, Jenna's biggest "what if" was about to unfold.