The Art of Breaking a Heart

I am not a serial monogamist.  Other than a handful of short lived relationships, I have been single for the better part of a decade.  I have been given excuses such as, "it's not you, it's me," "I miss you too much, and I can't miss you anymore," "we work better platonically."  Etc.  I have broken up with ONE person in my entire life.  Some of that is due to staying in a poisoned relationship long after it was dead, and waiting for the other person to end things, some of it has been due to some of my own short comings and neuroses.  Most of it has been men who have gotten tired of sleeping with the same woman.  (hurtful, yes, but essentially true, see: old cow.)

The one boy I ever broke up with was my very first high school boyfriend, freshman year.  We would walk through the halls at school holding hands until our palms were sweaty, and he would call my house every night.  After a week I was tired of him invading my personal space and taking time away from my girlfriends, so I dumped him.  I'm not proud of myself, but it is what it is.

Yesterday, I found myself in much the same predicament.  I had met a man, he is a very nice man.  He treated me well, lived here in town, and thought I was the bees knees (for lack of a better term.)  None of these were good enough reasons to keep stringing him along, (which is what I felt like I was doing.)

Do serial daters/dumpers get used to being the bad guy/girl?  Does breaking someone else's heart ever not break your own?  Because even though my heart wasn't in it, which is why I was ending things in the first place, my heart broke telling him that we could no longer pursue a romantic relationship.  My heart is still broken over the look on his face when I told him that we needed to talk.  Granted, I know that my heart will heal much faster in this instance than in any of the others, because, like I said, it wasn't all in.

Did all of the men who have broken my heart in the past, who have listened to me cry over the phone, or sat with me while I cried in person, had their hearts broken by the process of it as well?  It really can put things into perspective.  It shouldn't be something easy.  It shouldn't be something you're able to do without even thinking about it.  I know that most times one or both people know it's over long before the words are said, and maybe that gives the other person time enough, and courage enough, to find the right words to say. 

I am still at a loss for mine.