I usually shy away from discussing my romantic foibles with Gordon because I am always so mindful of the fact that he, himself, rejected me... and I don't want to give him cause to think about the fact that he rejected me--because I know that this is not uppermost in his mind when the two of us are hanging out.

I also shy away from wanting to discuss his romantic mishaps because it throws into sharper relief (for me) that I asked him out and he said no... this man who feels largely rejected by women, rejected me. I have lived out our friendship trying to sidestep this landmine, or to gloss over it, but it is a huge pit that has to be acknowledged.

He initiated the line of discussion, sort of.

He recently sang and played guitar for a friend's wedding; he confided that he's been asked to do this kind of thing a lot lately, and he said to me "Don't ask me to play at your wedding...I don't want to become like the Wedding Singer." I debated saying nothing because the comment was rhetorical, but in the end I couldn't help myself. I said "I won't," and left it at that.

We spent a lot of time talking about our anger at our parents and the ways we have felt failed by the poor guidance they provided to us. He mentioned finances and romance, specifically, calling these the two most deficient areas in his life.
Because it would have been traitorous to the conversation not to, I told him about the fact that I have been praying through the perpetuated stigma of rejection that seems to attach itself to every woman in my family. I told him that my entire life is a reaction to my mother, and not wanting to repeat her mistakes. I said to him "Well, I'm not in a bad relationship, but I'm also not in any relationship at all, because the minute a man expresses interest in me--even if I would be inclined toward him, I lose interest right away." I even told him that I am drawn to people who are likely to reject me.

All this in the context of the ways we both felt we'd aided and abetted our own miseries. He shared with me how he feels utterly disregarded and not known by his parents--in some ways, emotionally orphaned. And I also heard him be verbally protective of them, qualifying his statements by mentioning their good intentions, not wanting to paint them in too bad a light.

And I sat there in pajamas with a towel wrapped around my head, feeling that in spite of the fact that I'd gone out to buy beer and cookies for our visit, that in spite of the fact that I had coffee brewing--and that he was sitting on my couch, pouring out his heart to me, making me laugh--in spite of the fact that I was buying yet another painting--in spite of the fact that I said to him "It seems to me that you just want to be really, intimately known..." that it was not going to be enough.

I did not have a bad time at all; as is the case with most of our visits, it was very good, very full. And I didn't feel angst-ridden after he left or upset by anything he'd said. I just wonder if I need to get to the point where I make up my mind to be his friend and wish him love with someone else, someone he would really want. I feel so sad now, typing this.

He told me that he is envious of me; perceives me to have it all together... I told him that I am quite capable of irrational meltdowns, that I feel insecure a good bit of the time.

I am encouraged, though, that I see so many of my prayers for him being answered. For example, he's trying to quit smoking.