I think you make a good point. I've been the one who has ended all three of my long-term relationships and, at least for me, the more I tried to explain my reasoning for wanting to end the relationship, the more resistance I got from my partner. The more I pointed out "you don't have X quality that I really need in someone," the more she would say "oh, but I can develop X! Now we can be together." But I didn't want to be together; I was done. It became very challenging to try and explain my decision to the other person's satisfaction. I realized that the less I explained and the more I just said "please respect the fact that I am done and I need to move on"-- the better I was able to get the the person to respect my decision and stop contacting me.

I've found this to be a challenge even with causal dating. I went on a first date just over a week ago and did not feel a connection.she did. She has spent the last week texting me, trying to convince me that my feelings are wrong and I need to "wake up" and realize how great we could be together. At first, I tried to politely explain why I was not interested. It didn't work. Finally, I just had to stop responding and delete any further messages from her.

I don't think there is a "right" or "kind"'way to break up with someone or tell someone you aren't interested. It's always hard and often messy.