We first meet Sailor just after the loss of his sister, Sailor seems to be protecting his sister’s boyfriend Elliott, Sailor feels guilty about the feelings he has for his sister’s boyfriend even when she’s just died. Elliott gives Sailor a necklace, then tells him that he’s leaving early for college and can’t be around his father and the friends he and Rebecca shared.
A chance meeting with one of her student’s uncle’s and a fire has Sailor starting to like Jake, when he offers her somewhere to stay she says yes realising that she needs to start living her life again, even though Jake brought up memories of her past.
Jake makes Sailor want to break all her rules and she likes flirty Jake, and, agrees to stay but nothing prepared her for meeting her roommate, Elliott, her sister’s boyfriend.
Realising that she likes Jake, Sailor is surprised when Elliot tells her that he still wants her, leaving Sailor more confused.
The three have a history with each one having a different part of it being their own story, once most is out in the open, Sailor realises that she can’t choose between them and won’t ruin their friendship after what they have been through.
Jake decides that he has a solution and talks to Elliot, whether he solution is going to solve their problem or not, they both want what is best for Sailor, and hope their solution is what she wants as well.