Something has been lost in translation

At what point in time is it alright to hurt someone for the sake of making yourself feel better? I have always thought that such a horrible thing is never justified. But, I am beginning to think differently. I have, within the last week, broken things off with my obsessive boyfriend person. Gave the whole "it really isn't you, its me and my commitment issues" and "I hope we can always be friends" speech. I have tried with all that I am not to hurt him. But somehow, speaking kindly and gently, things aren't being understood. I don't mind if he calls me. Lots of people call me. What I do mind is the endless number of calls at all hours of day and night that go along the lines of,

"I just wanted to let you know that you're smart and beautiful and funny and that I love you and that I miss you and that I'm always thinking of you and I was wondering if maybe I could call more often and if you could be my girlfriend again. I'll back off more, I promise!"

Ok... um... so I have, as kindly as possible, said no to all said requests, stating that time apart, yadda yadda, is good and healthy. That we need the space to evaluate things, blah blah blah, and that honestly, even though I still love him, as a friend, that I have realized that I'm seriously not ready for such an intense relationship (and that the 357 whatever odd miles really don't make things any easier, either.) Sidenote, I think I could handle the distance if he hadn't, y'know, like proposed and what not. I think that I could do a long-distance thing. I shall think on this. Back on subject, so I thought I made myself pretty clear. But, apparantly not. And so I really don't know if I'm supposed to just keep nicely saying the same things or if, as some of my friends have suggested, just saying, "Matt, it's over. We are friends, but that's it. Please do not call me again if you are doing so to try to get "back together."

Honestly, that is exactly what I want to say and exactly how I feel, but I'm really not the kind of person who can just crush someone and be alright with it.

So here I am, standing here totally confused as to what to do, wishing that things would just disappear in a cup of coffee, having no idea what to do or what to say or what to feel or how. My head is pulling one direction ("just tell him DUDE! ITS OVER!"), my heart another ("no! be kind! You don't want to hurt anyone") and I am here between the two not knowing which road to take.