Kennedy (Kenna) isn't known for her beauty. She's never been complimented on her appearance unless being called beautiful by your family counts, and to Kenna- it doesn't. Sick of being ignored because of her looks, Kennedy gives herself a makeover but it isn't very successful. After encountering a crying Marissa Rivers on the behalf of her obnoxious brother, Noah, she becomes acquaintances with the girl. After a chat about Kenna's failed efforts at makeup and how she's a nondrinker, she offers Kenna the help of her and her friends. Kenna graciously agrees but there's a catch. Kenna will have to be the girls' designated driver to the next few parties that they want to attend until she can do her own makeup which may take a while but what happens when Kenna accidentally gets drunk at one of the parties and Noah has to bring her and the other girls back to their home? She gets involved in a lot more than she planned. And it seems as if all she wanted was to become beautiful.

Hadley Jamison doesn't know what to think when she hears that her classmate, Archer Morales, committed suicide. She didn't exactly know him, but that doesn't stop her from feeling like there was something she could have done to help him. So to Hadley's surprise, on the very night of Archer's funeral, she has a run in with Death himself and is offered the chance to go back in time to stop Archer from ending his life. The catch? She only has twenty-seven days to do it. And if Hadley doesn't succeed? Well, she doesn't want to think about that.