At sixteen, Journey Durant hasn’t yet experienced her first anything. No first boyfriend. No first date. No first kiss. But, that’s all about to change. Two boys at West Emerson High are vying for her attention: the MVP quarterback and the school’s reigning bad boy.

David Britton is the sensible choice. He’s attractive, responsible, and every mother’s dream—including hers. But, David and Journey are from two different social universes where David is the sun in his, and Journey is a moon rock in hers. He’s the most popular guy in school, and Journey is just background noise. She has a hard enough time accepting that he truly wants to be her friend, much less anything more.

And then there’s Steven Drake. Steven has dominated Journey’s fantasy life for as long as she can remember. He has a short list of things he cares about and school, the future, and what anyone thinks of him aren’t on it. Journey finds the element of rebellion he emanates to be intoxicating. But as much as Steven excites her, she knows there’s trouble down that road.

So, who will be her first? Mr. Most Likely to Succeed or Mr. Most Likely to Go to Jail?