What would your ideal retirement community look like?

Pro-tip: party with people who also love cleaning up at 7am.

This article on a Margaritaville-themed retirement community makes for an easy-to-smirk-at headline, but raises a lot of interesting questions if you bother clicking through. We’re about to have a massive aging population who aren’t going to quietly get consigned to traditional senior living. Our whole conception of seniors and their role in society — especially as they live longer and longer — is weird and undefined and in flux.

But on the matter of themed retirement communities this… actually sounds kinda fun? And even for those of us who have no particular fondness for Jimmy Buffet, it’s useful to think of what’s really important as we age and what the ideal scenario in which to spend our golden years might be.

What would your ideal retirement community look like?

What kind of space, what kind of people, what kind of activities would make your later years the most enjoyable? Where would it be? What would its theme or name be?

If we beat death and aging, would monogamy disappear?

Also dinners. If you can't agree on where to go to dinner, just quit now.

Also dinners. If you can’t agree on where to go to dinner, just quit now.


Whenever there is another news story (like this one) about how we’re inching ever closer to discovering the secret of “defeating death” or “reversing aging”, the easy immediate reaction is “whoa, cool, I can be immortal!”.

Leaving aside the fact that I personally think that sounds terrible (discuss!), the follow-up thoughts are a lot more interesting. Even if people don’t stop dying completely, and just lived much, much longer than they already do, there would be tons of repercussions for society. Economic, environmental, social.

For now let’s focus on one: relationships.

Conventional wisdom says that as life has extended, marriage in particular has been forced to change; that when life expectancy was shorter, it was more attainable to have a healthy relationship for twenty to forty years, but as people live much longer, can any one partnership possibly be expected to sustain itself for sixty, or a hundred?

And if we shift expectations that life will almost certainly extend a hundred years (or two hundred, or more!), it seems likely that our expectations on how any one relationship could last that long will have to shift too.


In a world where people live twice as long, how do the parameters of long-term relationships have to change to accommodate?


Would people still try to partner up and stay together “til death do us part”?


Shift into more open ongoing relationships with multiple partners?


Accept that a series of long-term but non-permanent relationships can be satisfying for all involved?


Or do we just give up marriage all together?

Which celebrities, past or present, best represent your worldview?

Full/Sad Disclosure: Lelaina from Reality Bites is the fictional character I would have most absolutely married. Possibly still.

Full/Sad Disclosure: Lelaina from Reality Bites is the fictional character I would have most absolutely married. Possibly still.


As a fan (and a 30-something human guilty of some of the perceptions the article diagnoses), I thoroughly enjoyed this in-depth look at the career and symbolism of Winona Ryder, “Winona Forever”. It’s full of interesting stuff on how an actress represents a generation, how an individual gets trapped in time because of that symbolic role, and so much more.

“If you spend your most crucial adolescent years being watched by millions of people being told what’s good and what’s bad, you have no sense of who you are,” Ryder explained. She saw a therapist who diagnosed her with “anticipatory anxiety” —feelings of dread over anticipated events—and, quaintly, “anticipatory nostalgia.” (In the Times,psychologist Dr. Constantine Sedikides recently described this lesser known “condition,” which could be considered our current era’s raison d’être, as the drive to “build nostalgic-to-be memories.”)

“To us, Winona Ryder is a bona fide icon,” designer Marcus Wainwright said. “She also has this beautiful timeless quality.” But it’s actually her timeliness that gives her value—she is a human incarnation of ‘90s nostalgia.

We cannot see Ryder without seeing the grunge era. In the New York Times Magazine in 2011, Carl Wilson riffed on the “20-year cycle of resuscitation” that had finally turned to Gen-X nostalgia.

As Tavi Gevinson told Entertainment Weekly in 2014, “how I feel when I see pictures of teen Winona Ryder and Johnny Depp holding hands in leather jackets, like, nobody can match that.” The only person that can come close is Winona Ryder now, because embedded in Winona Ryder now is Winona Ryder then. She carries her past with her. The teen actress who sought to make her own life nostalgic before it had even passed her by peeks out from within the woman Marc Jacobs now imbues with nostalgia—she is a Russian nesting doll of reminiscence.

Sorry for the overbearing quotation, but there’s just so much to unpack here! Let’s go most straightforward to most abstract:

Which celebrities do you feel represent your youth, or your most core values and beliefs and personality that will never really change?


As they get older, and you get older, how does that connection change?


Do you ever feel “anticipatory nostalgia”, the need to create memories to remember later? Is that a useful or healthy tendency, or anti-social, neurotic, and potentially detaching you from authentically enjoying your experiences?


how would people describe you now vs 10 years ago?

Other than "you're fatter".

Other than “you’re fatter”.


Running into former coworkers you haven’t seen in years, changing jobs or cities after extended periods of routine and complacency, those miserable years when a high school reunion rolls around to remind you of your mortality — there are these rare instances where you’re faced with thinking about how much you’ve changed, whether intentionally or without even realizing. A mini version of this happens around New Years every year, but widen the scale and it gets a little weird and frightening. Or impressive and exciting! I guess that depends on you.


How would people have described you 10 years ago, and how is that different from how they might describe you today?


What would be different if the person describing you, then or now, is someone that knows you well versus someone who just met you?


Which qualities do you wish you still had from the past? Which are you glad to have gained or lost since?