Lenny has been a bit of a mess since her best friend, Lou, passed away. She's avoiding her concerned parents, her apartment and the list of things she's supposed to do to enjoy life again. The only thing she can handle right now is babysitting a precocious seven-year-old, Ainsley. And if Lenny acts like she's fine, maybe no one will notice she's falling apart. The only issue: Ainsley's uncle, Miles, is always there and is kind of . . . a huge jerk.
But Miles sees right through her. He knows a lot about grief and offers her a deal: he'll help her complete her "live again" list if she'll help him re-connect with Ainsley and his sister. Lenny doubts anything can help, but as she begins to spend more time with Miles, she begins to see that, sometimes, losing everything can be the first step to finding yourself again.