Recently my near-fifties Philly friend Jay was forced to find an assisted living facility that could accommodate both his parents in a single unit since they each have been incapacitated by a stroke. They will never be able to return to their suburban condo without round-the clock assistance, which would cost tens of thousands of dollars. As a result of that experience, Jay e-mailed me concerning his retirement fears.

He went on at length to express his dismay.

Well, hell! At my age my opinion is asked so seldom, that I jumped at the chance to respond to my fiftyish Philly friend.

"Dear Jay—Thanks for your e-mail and for honoring me by even thinking I might have retirement lessons to share. If the aging process has impressed me with anything it’s how little I know and can share, not how much. I chuckle frequently at the concept I had in my younger years that someday all the pieces of my life would fit together into a neat comprehensible picture and that I would attain some semblance of wisdom. I fantasized that at some point I’d reside on a desert mountain top contemplating my navel and dispensing pearls of wisdom to life’s pilgrims. Let me tell you, friend, it ain’t so. The older I get the more questions I have concerning the riddles of life, and I have fewer answers.

But I want to encourage you. You are definitely on the right track by thinking about retirement options now while you are still young. Most retirement planning seems to focus on the how—the money needed to accommodate you in the manner to which you are accustomed. In your case, that might mean dusting off your drag outfits and marrying Donald Trump the next time round.

The "where?" is equally important with the "how?" The fact that you are considering staying in Maine through December is a sure sign that the stress of dealing with your parents situation has addled your brain, or that your shrink has shrunk from his responsibility of pointing out that you are crazy. But if that’s what pushes your Blackberry, go for it. My experience of being a two home seasonal resident in the past was that it didn’t work for me. I never felt fully part of either of the communities where I resided.

Furthermore, the people-focused activities that I enjoy the most and that give meaning to my quieter years can’t be done for a few months here and a few months there. It took me several years of being a transient, however, to realize that, and your experience and desires may be different.

I’m also glad that, very realistically, you give a high priority to who you’ll have sex with as you grow older. I’ve not lived in a gay or a straight retirement facility but I can assure you that the interest in, and the need for, sex doesn’t evaporate because you’ve passed a certain generational marker or moved into a retirement complex. Knowing you, I’d suggest that you extend your planning and find out what opportunities for sex there might be among the grave diggers. It ain’t over ‘til it’s over.

The flaw that I find in your planning to date is that you are limiting yourself to gay retirement communities. The last time I checked there were only a few such facilities nationwide and all of them were limited to independent living. By the time your considerations require action there will without question be additional gay and lesbian facilities available and some may include assisted living. But the possibility of a gay facility that will offer the total gamut of independent living, assisted living and ultimately nursing care, seems unlikely. If it could be done anyplace it would be in a gay urban center like Fort Lauderdale or Miami and I’ve not heard even a whisper of such an undertaking.

For that very reason several of my gay and lesbian friends, who are currently living active and comfortable lives independently, have placed their names on the list for admission to total care facilities. They recognize the desperate situation they might be in when their partner dies and assistance from friends and relatives may be limited—or non-existent. They also want to be able to move from independent living in their own home or apartment, to assisted living when necessary, and to nursing care, if needed, with a minimum amount of upset. To their credit, like you, they are planning ahead.

Within my own family, as well as with friends, I’ve found that these crucial decisions are usually made when a devastating health crisis develops, and that’s too late in the game. It’s best to plan ahead and move toward your retirement goals, rather than flee from a current disaster by necessity.

Kurt Weil had it right. "It’s a long, long while from May to December, and the days grow short when you reach September." But they’ll be better days if you start planning for them in May and June and July.

My love to you both. Come visit when you can and check out both a warmer climate and the vibrant gay community in Fort Lauderdale and I’ll give you a personal tour of facilities where sex at seventy-seven is the norm. There’s nothing magic about seventy-seven. I just like the alliteration.

Maybe you’ll find four months in the sun isn’t enough."

With lots of love,
John