The 36 questions that lead to love — on Martha’s Vineyard

You can tell a lot about someone by how they relate to the Island. Maybe even enough to make you fall in love.

—Illustration by Kate Feiffer

Last Valentine’s Day, Mandy Len Catron wrote a New York Times “Modern Love” essay titled “To Fall in Love with Anyone, Do This.” By “this” she meant sit down with someone, even a stranger, look into their eyes, and ask each other a series of 36 questions.

The questions were designed to accelerate intimacy and accomplish in an hour or so what might ordinarily take months, years, or perhaps never happen at all. They asked questions like, “Would you like to be famous?” … or “When did you last cry in front of another person?” … or “What does friendship mean to you?” The questions were divided into three groups, with each group intended to delve a little deeper into the psyche.

What makes this more than just a parlor game is that it was devised by a psychologist 20 years ago, and when Ms. Catron conducted the quiz with someone she described as “an acquaintance” — boom! They fell in love and got married.

Since we’re approaching Valentine’s Day, we thought it would be fun to revisit the 36 questions and take them a step further. Since everything about living on the Vineyard seems to have its own unique twist, why should falling in love be any different?

So we contacted a lot of our friends, and asked them to help us create a new set of questions that would help people find their soulmates — not just anywhere, but here on Martha’s Vineyard. Not surprisingly, we got an array of responses ranging from the ridiculous — “What would you ask a straight single man to bring to a potluck in West Chop so he doesn’t bring bologna?” — to the sublime — “What about the Vineyard supports who you are?” We culled them down and organized them into three levels.

Now it’s up to you. Find a partner. Go through the questions. Don’t hold back. And prepare to start picking out china patterns.


When you say “club,” are you thinking golf, yacht, or P.A.?

What’s your favorite thing to do at the Ag Fair?

Do you bother to suck the meat out of the legs on a lobster?

Would you consider eating the Chilmark Tavern hot fudge sundae before eating your dinner?

What would you name your own bowling team at the Barn Bowl and Bistro?

Frisbee golf or real golf?

Would you rather wait in line for a warm apple fritter at Backdoor Donuts or a book signing with Hillary Clinton?

If you could have only one, would it be an American Express card or an Island Club card?

Would you wear a Black Dog T-shirt?

How many blue tarps in a yard are too many? Green tarps?

Capawock, Film Center, or Edgartown Cinema?

Would you ask a stranger to check you for ticks?


Do you go to the Dumptique? To drop off or pick up?

Do you wave cars in front of you at Five Corners?

If you could do anything with Boch Park, what would you do?

Who would you most and least like to see naked at Lucy Vincent Beach?

When asked for directions, did you ever just make stuff up?

When you get on the ferry in Woods Hole, do you feel like you’re already home?

Would you park at Homeport and then walk down and eat at the Galley?

Do you pick up hitchhikers?

Complete this sentence: “I went to Cronig’s and I couldn’t believe … “

Would you ever own a Humvee?

Did you ever flip off a moped rider?

Whom would you rather have greet you by name: David McCullough, Spike Lee, Carly Simon, or Trader Fred?


What is your most treasured Island memory?

What’s your guilty Island pleasure?

What do you feel most grateful for on the Vineyard?

Would you rather have dinner at L’Etoile on a warm summer night, or go skinny-dipping?

What would you change about the Vineyard?

Choose one: Bike paths or Bodhi Path?

If you could wake up tomorrow with land anywhere on the Island, where would it be?

What would be your perfect Vineyard day?

You have the day off in the summer; it rains like crazy. What do you do?

Given the choice of any Impossible Dream, which one would you like most to win?

If you missed the last boat home, what would you do?

Where would you want to get married on the Vineyard?

Do you have some questions you think might lead to love on Martha’s Vineyard? We’d love to hear them: