I wonder if this will be a new one. Last spring, my cherished younger brother died suddenly (get a CAC scan everyone, not joking, Google it), and I got a call from a friend of his who moved across the country maybe twenty years ago, and who I last saw maybe fifteen years ago. He really loved my brother and was terribly broken up. We've stayed in touch every couple of weeks or so. I loved having someone to be sad with about my brother. We talked about other things too, everyday stuff. He was in a good ten-year relationship, involved with his SO's kids and grandkid. Put her on the phone with me a couple of times. She was having severe back problems, had had one surgery and another was planned for September. In the course of one of our conversations, he told me that he loved me, and has since we first met. He was quite definite about it. There was no flirting or anything (for sure on my part there were zero thoughts along those lines), it didn’t feel untoward; I read it as in the category of telling someone you had a crush on them back in the day. My response was something like “awww,” and then the conversation moved on. He mentioned it again once or twice. He wanted me to know he wasn't making it up, but didn’t dwell on it.

About five weeks ago, his SO had her second back surgery. Something went wrong and she died a few days later. He was appropriately broken up about it. We’ve talked a couple of times since then and when he called yesterday, he told me that he was serious when he said he’s loved me all these years, and asked me if there might be a possibility in the future. And that he's considering moving back here to be close to his family. My response was that his grief is new and raw and this is definitely not the time for any conversation like that or big decisions. I did agree that if he comes out to see his family next May we could have a visit, but that we barely know each other and he shouldn’t expect anything at all.

I do want to be supportive to this guy, Dan, like he was for me, but I don't want to be a grief-avoidance proxy. Not to mention the icky feeling of this happening practically on his SO’s grave. I know grief can make people crazy and it may burn itself out, and that would be fine, as I honestly have no idea if there could be interest on my end. At the same time, based on his disclosures when he had a full life on the other side of the country and there was no question or hint at all of anything ever coming of it, I believe what he says about his feelings. And I do like his brain, always did.

Did I mention that I’m 60 and after a couple of go-rounds have been working on coming to terms with the idea of being alone for the rest of my life? Not my preference, but I’m making it work. Suffice to say my judgment has not been great in the relationship area. Do I tell him to call me in six months or a year, or continue talking occasionally in supportive friend mode, which he could use to sustain grief-avoiding hope? Or what?

Your thoughts, Dan?

Your Clever Acronym Here

I want to say you have plenty of time, what's the rush, take it slow... but then I keep coming back to the sudden and unexpected deaths of your brother and his old friend's SO. A friend of mine died last week—oh, Jonathan, you were such a beautiful man—so who really knows how much time any of us has left?

So, yeah, given the context and the feelings of mortality your letter and the death of my friend have stirred up... I'm inclined to say go for it.

With the understanding, of course, that "going for it" doesn't mean "get a place together today." Your brother's old friend isn't talking about moving home next week or moving in with you next month. He's not talking about abandoning his SO's kids and grandkid in their grief. He's talking about meeting up with you when he comes home to visit family in May, seven months from now, which seems entirely reasonable. And he didn't try to extract a premature commitment from you; he asked if you might be open to the possibility, YCAH, and he qualified his open-to-the-possibility ask with "in the future." So he's not rushing himself (in his time of grief) or rushing you (which would be highly manipulative of him). And it sounds like you are open to the possibility. So tell him that.

Here's what you also need to tell him: you haven't seen each other for the better part of two decades. The image he has of you in his head might be—most likely is—highly idealized and even if he comes home and you two hit it off and it feels right... you're going to want to take things slowly. You'll need to really get to know each other before you make any decisions about going public with your relationship or moving in together. The real you will have to supplant the idealized you he's been thinking about all these years, YCAH, and you're not in love with him at the moment—you're open to the possibility that you may fall in love with him but that will take some time.

May is a long way off and he will have a better handle on his grief then. So keep talking and then meet up in person and see how you feel then.

P.S. When it comes to love... the older you get, the more important liking someone's brain becomes.