Sam is a 'confirmed bachelor' in every sense of the word. He just doesn't have time for any serious relationship with his erratic work schedule and he likes 'playing the field'. His life begins to take a turn after he meets a six year old girl who warms him to his soul and opens his heart to the possibility of something more when he meets her mother Jessie.

Jessie is a single mom trying to get through college while living with her parents until she can get on her own feet. She has sworn off men since Peyton's father walked out on them four years ago and the few dates she has gone on since have only lasted until they found out she has a child. She has resigned to the fact that her chance of love had come and gone, that is until Peyton introduces her to Sam.

Jessie makes it perfectly clear that friendship is all she can offer to Sam as she has her daughter to think about. Sam agrees to her friends only relationship, but when he steals a heated kiss it forever changes everything between them...