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 your legacy is the people whose lives you reach, LOOK AT THAT LEGACY.

Jon Stewart took over The Daily Show in 1999, the year I graduated high school. (I was a fan even before, of the sillier Craig Kilborn version). Since then, I think I’ve barely missed an episode. In college, he was our nightly news, a break from studying. Since then — and my acquisition of a DVR — he became a dinnertime companion, watching his take on the previous day’s news over a meal, catching up even on the days we missed because his service was so invaluable.

His show made current events engaging, and more importantly made our problems palatable.Through the difficult Bush years, he offered catharsis. Through the bizarre upheavals of the Obama years, he offered a voice of reason. And always intelligence, always laughter.

Thinking about his departure, I don’t know if there’s a single other person in entertainment I’ve spent as much time with as Jon Stewart. (Maybe The Simpsons, but that isn’t quite the same.) Leading up to his final show, I felt a strange clenching in my chest. It wasn’t sadness, like you’re preparing for a loss. At least not only that. The closest comparison I can make is saying goodbye to someone you loved in high school. They’re always going to be a part of your life. In many ways they helped make you who you are. But now it’s time to move on, and you both know it. You may see each other again some day, but it’ll be different. But that’s okay. The time you had was unforgettable. Invaluable. And you leave with a little bit of dread, but also gratitude. Grief, but also joy.

Which celebrity have you spent the most time enjoying? Why them? How did they affect your life?

If any current celebrity suddenly went away, which one would be the biggest loss, the biggest blow to your life, would leave the biggest hole?

For me it’s Jon Stewart, and there might never be another one bigger.

Thanks Jon.

Also you can’t pick Canada.

The reason isn’t important, but say you had to leave the country right now and never come back.

You have to decide right now which country will be your home for the rest of your life. Pretend that upon arriving in that country, you would immediately understand the local language perfectly, so that’s not a barrier.

You wouldn’t have a job or friends in that country waiting for you (if you have friends all over the world, pretend you don’t), so you’d be starting fresh with whatever you currently have.

And once you choose, you can never leave that country for the rest of your life — so considerations like speaking a language lots of other countries speak or proximity to other places you want to travel to on vacation shouldn’t weigh in. Though you can still speak your native language, so watching American TV or calling your parents aren’t a problem.

But once you choose, that’s your home until you die.

Where would you decide to live out the rest of your life?

If you want to make it even more interesting, choose a place you’ve never been before.

*somewhat inspired by this week’s This American Life episode, Abdi and the Golden Ticket.