What do you do when your dead best friend’s last wish is for you to go on dates with her boyfriend?

When Addy Taylor died and left Jessie basically without a friend in the world, Jessie thought that was it for her. She had been living in the Taylors house since she was ten, but now that their daughter was dead, Jessie couldn’t possibly ask them to stay. But when Addy’s dad gives Jessie a letter from Addy, Jessie clings to the hope that Addy left instructions for her to find a way to move on. What Addy actually wanted Jessie to do, though, is to date Addy’s boyfriend, Andrew. 

Jessie has a hard time being around Andrew and can’t imagine dating him. What would the Taylors think? But Addy promised in the letters and videos that she left for them that she’d tell them each secrets she hadn’t shared with anyone else if they went on the dates she had already planned and paid for. Desperate to not let go of Addy just yet, Jessie agrees to the elaborate date that Addy has planned for she and Andrew. 

With each letter that comes and each new date that follows, Jessie finds out that Addy was hiding more than Jessie could have ever imagined. She also discovers that—despite everything—her feelings for Andrew grow with each new adventure they take. Even though Addy gave her permission, Jessie can’t help but wonder how bad of an idea it would be to fall in love with him. Because that would mean that she’d replace Addy, and Jessie still didn’t even know who she was without her….