"This is getting too risky," "You ain't seen nothing yet baby girl,"

Jack Gilinsky is Beacon Hills High biggest heartbreaker. He strings girls along then drops them as if they meant nothing. Secret is Gilinsky doesn't attach himself to anyone because he's secretly afraid of heart break. But all that changes when the new girl Lydia Forbes comes into the picture. Lydia isn't all that interested in Jack at first, but he eventually strings her along as a bet. But he's shocked when he starts to catch feelings.

Emmalyn is just an ordinary teenage girl in high school. She is not quite a good girl but she isn't bad either. What happens when she crosses paths with Jack Gilinsky, the school bad boy. Is he what she thought or he was or will something change her mind?

Jack and Jack have been best friends since kindergarten. But what happens when Johnson's little sister and Gilinsky go a little further and break their "best friends little sister" and "brother's best friend" bond?

June, Jack and Jack are best friends and have been since they were all in kindergarden. They are all with someone, but what happens when Jack can't help but slowly fall for June while he is with another girl. June and Jack are the best of friends, when Jack confesses how he feels, does she feel the same way?

"I've learned that you can keep going, long after you think you can't."

Izzy Taylore is just like every other girl in Omaha. The only difference is who her best friend is. Jack Gilinsky. When they finally admit how they really feel for each other they navigate from friends to dating.

Lakyn Ellis is just a normal 17 year old girl in Omaha, Nebraska but with over protective parents. When her parents won't let her date anyone her and Jack Gilinsky have to find other ways to see each other. But what will happen if her parents find out?

What will happen when Caroline moves to Omaha and Jack Gilinsky is her neighbor?