First of all, I love your question! I've had to go through this recently and I am so happy to share my hard-learned lessons.

Secondly, I'd like to start by asking you to think about a few questions, yourself. 1). Is it truly necessary for there to be a, "clean break?" In other words, are you positive you have to pinpoint a moment to verbally and officially break the friendship off? I ask because break-ups, when done succinctly and concretely, can feel like a miniature death. One minute, the person is part of your life and the next, they are not. The residual feelings can be depressing, horrifying and saddening, to say the least. There is recovery time needed and it's a difficult to experience the stark contrast of before and after.

If you feel that it is, indeed, necessary to have "the talk," then I encourage you to be as open, honest and considerate as humanly possible. Tell him, or her that you have appreciated her friendship, that it has had its positives, and you will never forget those. Tell her that you feel (to avoid defensiveness on her part, it is important to phrase everything as opinions and notions of feeling rather than fact) that the friendship is no longer beneficial to both of you, nor making either of you happy and it's probably best that you part ways. If your approach is kind, you can walk away from the encounter with your conscience clear and your head held high.

Often, when a relationship of any type goes sour, I believe it's human nature to want to hash out the details, discuss the wrongs and fight the fights that surfaced in the friendship. The residual loose ends and remorse that harsh language can cause may prove to haunt you later. Picture it like mending after a boxing match. Both fighters give their all, but have broken noses and swollen eyes that take weeks, even months to heal before they are healthy again. Therefore, I strongly discourage "finger pointing," blaming, arguing, or attacking (even though you may REALLY want to fight back for a wrongdoing you have suffered).

I believe, in the long run, you will feel better if you walk in confident, strong but sympathetic. We often mistake confidence for "telling it like it is," being straight forward and saying what we feel needs to be said. True confidence in this situation, I believe, would be to foresee that you may regret being cruel and she may be cruel in return (again, picture the two boxers). More unresolved feelings and loose ends can arise from this. Stay calm, deliver your compassionate message and move on with your life.

Now, if you answered "No," to my above question about whether, or not there needs to be this discussion, then there is a less confrontational way to dissolve a relationship. You can start by saying, "No thank you," to any invite, or request made to spend time. If queried why, reply politely that you are busy. You could be washing your hair, cleaning your bathroom, or simply spending time with yourself. In actuality, you are too busy to maintain friendships that are unhealthy, or harming you in any shape. You are too busy trying to lead a happy and productive life. This allows the door to remain open for courteous discussion in the future should you run into your friend. Trust me, your absence will be noticed and understood over time.

2). Are you positive this friendship has reached its' finale, or do you have any reservations about ending it? Is there maybe a, "cooling off," period needed, during which any bad feelings may dissipate and you may start to miss your friend? Remember the positives? I ask because, to this day, I do have fond memories of exes and old friends. For a very few, however, the pluses were not enough to warrant a return to my good graces and the relationships have ended. There have been times, I shamefully admit, that I thought about throwing ultimatums, or ending friendships because of fights and arguments. Concluding certain relationships would have been terrible mistakes; while keeping others would have been also. When you have thought this over thoroughly, I again advise that you act compassionately and firmly so you may feel good about your actions for a long time to come.

Best of luck to you witht his difficult decision. Please feel free to write me if you want me to clarify, or share my personal "friendship ending," story.