There’s a boy that crushed my heart over a year ago by ending things because he wasn’t in a good spot nor ready for a relationship. I (mostly) saw it coming, but that didn’t make the end of what we had any easier. I eventually got over it, and my feelings for him changed from sadness to awkwardness to varying degrees of annoyance. Finally in March I felt a-okay about things and ready to pursue a friendship with him. Only to discover that his continual attempts at keeping in touch were continual attempts to get back together. That’s led to bouts of messaging each other every two or three months because we’re both too stubborn to realize we’re both looking for different things and cling onto false hopes that he’ll want to be buddy-buddies (in my case), or that there’s a second chance to continue something romantic (in his case). Aside from giving Gerrit and I another chance, I’ve never ever attempted dating someone twice. Either I broke up with them for a legitimate reason, or romantic feelings subsided and I wanted little to do with them or I couldn’t imagine pursuing something more than a friendship. I don’t have a hard time letting go of relationships most of the time, but I have a hard time letting go of potential friendships, especially because it’s not like things ended on a harsh note.
I made the biggest mistake of my life in dropping off the map with you. I just wish I had been in a better place. I want to thank you for everything you did for me. I really liked you but wouldn’t accept it for myself until it was too late. You are without a doubt the nicest, best person I have dated, and I don’t expect to find anyone near as good as you in this town.
For someone I cared immensely about and made a lot of special memories with, receiving texts like that doesn’t make the decision any easier. But for as long as it’s been since we stopped dating, I think the kindest thing I can do for both of us is to let go.