Back in college, Dianna Sheldon made a pledge to the Saving It Sisters, promising to save herself for “The One.” As her thirtieth birthday approaches, Dianna decides to break that pledge before she reaches the milestone. But she discovers that attempting to break a promise is not as easy as it seems, especially with her best friend, Sean, blocking her every step of the way. Sean Donovan has always been a wild child, but Dianna managed to keep him grounded. When she tells him she wants to lose her virginity, he makes it his mission to stop her from making a huge mistake. Adriel, Dianna and Sean's guardian angel, can't stand by and watch them head down a path that will lead them away from each other—and their "happily ever after." So he enlists the help of the archangel Jude, and together they come up with a plan to save these two souls. They send down two rookies to nudge Dianna and Sean onto the right path and, with any luck, right a sixteen-year-old wrong.