Many readers have pondered Anita and Edward's relationship, and how far it could go. Many think the books give very subtle hints about deeper feelings the two could possibly harbor for each other. Anita has denied any romantic feelings towards Edward, and vice-versa. Much of their relationship is poked through in Obsidian Butterfly, the ninth book of the series. Some of the mystery surrounding Edward comes to light in this book, even though there is still much more about him that has yet to be revealed.

After Obsidian Butterfly it seems apparent that the two admire and care about each other. They have saved each other's asses a lot. They know a great deal about each other, and as much as they wonder about who would come out on top (if they ever had a showdown so to speak), they don't intend to find out (at least for now). It is quite possibly one of, if not the most, strangest friendships/associations in the series.

Edward and Anita openly admit to each other that they've never had a romantic thought for the other. They even go into a talk about how they couldn't love each other because of the way they live and the work they do. Anita knew practically nothing of Edward before she met him. She trusts him, yet at the same time she ponders how far he would go for the love of his work. Edward has made it clear to her that he will torture her if he finds out she is withholding information from him. Anita gets scared when she thinks of the possibility of Edward coming to kill her. He even mentions that his ultimate fantasy is having a showdown with Anita, seeing which one can hunt the other down first and move in for the kill. Anita believes it is more likely of Edward killing her off first; she admires yet fears him because of this.

Yet when the time comes that Edward is given the opportunity to kill Anita for a huge sum of money, he turns the job down and decides to protect her instead. He figures he'll get to kill more people if he protects her, instead of just killing her and getting the job done. This occurs in The Killing Dance. He even gets somewhat worried, and when Anita is almost finished off in the bathroom of a club, Edward seems to feel somewhat guilty for arriving too late (Anita gets injured, but not killed). Much later on in Obsidian Butterfly, Edward even assures Anita that he'll be there for her to get her out of trouble.

Towards the end of OB, Edward gets a nearly fatal wound; he gets a stake driven into the left side of his body, barely missing his heart. Shortly afterwards, Anita is seperated from him, and upon hearing news from Olaf that Edward is alive brings her a great deal of relief. When she visits him at the hospital, he notices her distress and asks her what is wrong, to which she answers "It couldn't just be because you nearly died." By the end of Obsidian Butterfly the two have confirmed that they are friends, and Anita thanks God that Edward made it through.

This is more or less a summary of what has happened between the two thus far in the series. What readers make of it is their own thing, but so far there has been no real romantic thing going on between Death and the Executioner.