Kyle is a young well-bred billionaire who does everything by the book including going on the several dates that her mother sends him to.

One night however, everything changes for him, after spending the day at the best friend's wedding he gets him feeling emotional and after working through the night decides on a night cap.

In the kitchen he bumps into Maggie a sweet young ambitious girl who is studying for her classes. He is immediately impressed by her and strikes up a connection with the help.

Sadly for him Maggie comes with baggage, a whole bucket full of baggage. He tries to stay out of it but Maggie does not stay out of his head.

Will he get involved? Or rather play it safe and by the book?