Annie and Ben marry in their late teens, but due to her parents disapproval have the marriage annulled. Their lives both become complicated as they are both preparing for independent marriages later in life, and discover the annulment was never filed.

Blake Conway, aspiring journalist, hopeless romantic. and frustrated with the lack of chivalrous guys her own age, a college senior gives up on dating for love to date an older man in exchange for gifts instead.As she documents the adventure in the hopes of winning a journalism award with a generous cash prize to escape looming student debt, she sets out on a quest to figure out if society is right to judge these women and if her own self worth comes with a price.

When star high school athlete Eric needs help with his school work, Emily convinces Eric's mother Carol, that she is perfect tutor for her son but she has other reasons to that stem beyond helping him with his homework.

Through her attempt to ignite a romance with a much older man, Sarah, a fiercely independent teenager, learns to appreciate not only her youth but also her overbearing mother.