A couple of articles to get thoughts going:

Loneliness...

...in middle age.

...in the gay community.

(If you have other good articles for other sub-groups or aspects, sure, post 'em.)

As for me, I relate to the "in middle age" part, as I'm just too busy to have any sort of regular -- or irregular -- time to get together with a friend.  Difference is, I don't really miss it, for now at least.  I feel some unease as if I should miss it.  

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Reminds me of a poem I wrote several years ago - before I got married. I published it in the comments thread in "Dead Poets". The title is "The Empty Seat"

There’s an empty seat beside me; vacant by my choice.

I chose to live alone and free, with no companion voice.

I savored solitude and silence, unbound by another’s will.

But lately in the seat I sense a void that joy could fill.

 

 

There’s an empty seat beside me, though many there have taken rest.

And some clung to it dearly when I tired of it’s guest.

But I’d given my disclaimer when beauty settled there -

I‘d remind her who she knew I was, when she started the affair.

 

                                 

There’s an empty seat beside me that I dread when I come home.

Temples grayed and youth has fled, my selfishness outgrown.

Each night I retire to an empty bed and wonder - is it too late to meet

A partner I could love and wed, to fill the empty seat.

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