Will Sayre, a young, successful businessman wonders if he should ever be married. The more he learns from his friends about marriage problems and divorce, the more he leans toward staying a single man forever.
Renee Woodson is a single mother with an adorable 6-year old daughter named Rebecca. Rebecca’s teacher, Kim, happen to be Will’s sister, who tells him about the life struggles this little girl and her mother are going through.
Will finds himself thoroughly enjoying romancing Renee around the city even though his best friend Patrick and his basketball buddies warn Will about getting involved with a woman who has “excess baggage” from previous relationships.
Well-meaning girlfriends warn Renee, recounting their experiences about all the bad and disrespectful men, concluding that Will must be hiding something and is too good to be true. When Renee confronts Will and criticizes him, he is taken aback and can’t understand her “crazy behavior”. Will’s married friends tell him that they cannot make sense of why women do the things they do.
Confused and bewildered by their friend’s relationship advice, Will and Renee create complete chaos and misunderstandings. Yet after, some long awaited sound advice from key sources, both Will and Renee are encouraged to give romance another try, but is it too late?