When Samantha Adams learns that her grandmother has passed away, she feels little sadness for the woman she can't even remember. The only thing she knows about her is that she turned her back on her family years before. So it's a bit of a surprise when a package arrives bearing Samantha's name, containing letters to her and mementos that belonged to her grandmother. She discovers that her grandmother has included her in the will with one caveat. Growing up in the seedier parts of Boston, Ellis Hudson knows her way around the lowlifes she defends. She fills her life with one night stands, since the woman she loves is straight and completely unavailable. Instead, she settles for best friends. She's also struggling with her own doubts about her career and what she wants to do with her life. With nothing more than some letters, a map and a few names, they set out on the road trip of a lifetime. Along the way, they meet different people who knew Samantha's grandmother. Samantha realizes that each memento is a piece of her grandmother's memory of those people and she starts to return them. Along the way, she realizes her attraction to Ellis was more than just a drunken thing. The journey also challenges Ellis' will to remain just friends. Will they take the life lessons that Samantha's grandmother teaches them and finally follow their hearts?