By Amy Shearn
1. Ask Someone About Seahorses. Or Elephants.
I love seahorses. I shouldn't even have to explain why, because they are clearly so awesome: They look like weird fantastical creatures; they live in water but can barely swim; the males gestate the babies; they can live in the Hudson River. In short, they make no sense. I am always happy to share my seahorse obsession with someone—at a party, at my co-op building mixer, waiting to pick up from toddler ballet—and I've also found most people love telling me about their beloved beasts. Er, except for the cab driver who told a harrowing tale of being charged by an elephant as a child in Ghana. Everyone, besides him, has a critter they're dying to wax poetic about, if only somebody would ask….
2. Slap a Smartphone on Your Forehead.
As anyone who's ever taken an improv class knows, there is something about being goofy that creates an undeniable sense of camaraderie, which is the logic behind the latest flood of grown-up games meant to break the ice at bars (and parties). Heads Up! is a game app (developed from the game Ellen DeGeneres plays on her show [http://www.ellentv.com/2013/05/02/download-ellens-new-app-heads-up/] that requires you to hold your phone up to your forehead, so that others can see the word displayed there (but you can't), and then to guess the word using clues given to you by your fellow players. In other words, anyone can play it, and it essentially forces everyone involved to be at least 73 percent silly. Another good game-app to get people to loosen up is Word Party. And, of course, there's the old standby Trivia Night (don't worry, it's an app now, too, called Trivially).
3. Ask About His Last All-Nighter.
So, you're on your seventh Match.com first date, and you think you've gone through all your conversation starters. Well here's one you probably haven't used before: "When was the last time you stayed up all night?" Sleep (or lack of it) is easy to talk about (unlike, say, politics) and, what's more, if someone did stay up all night it was probably for something special—a person, a project, a dance marathon, a Netflix binge. And let's face it, there's something inevitably flirtatious—and conversation-starting—in asking about someone's night life.
4. Play "Where'd You Rather?"
Surely you recall the NSFW college-era game of "Who'd you rather?" Here's the SFW version: On a gorgeous sunny day when you're all stuck at the professional-development thing, ask someone, "If you could be anywhere else right now, where would that be?" On a miserable, pitch-black night, as you trudge through the snow. In the waiting room. You'll learn something about someone, and you'll give them a three-minute-long imaginary vacation while they talk.
5. Put on Your Track Suit.
For their short film The Runners, London filmmakers Matan Rochlitz and Ivo Gormley approached runners and interviewed them—figuring, as they told The Guardian, that the runners would "be distracted; perhaps you could ask about things that you couldn't otherwise." They found that the runners were often very willing to open up to them, frequently even offering advice: "I had a conversation with a woman who told me about her regretting not having had children and how it was now too late…," said one of the directors, Ivo Gormley. “[She said,] 'Take care of the present, because it's all you've got.' We smiled at each other and she ran off." So lace up your sneaks, hit your stride (walking works, too) and ask the big questions. It's a good way to get a parent, or cousin, or in-law to break out of chitchat mode.
6. Share Your Worry Wheel.
Artist Andrew Kuo created one of the loveliest and most hilarious infographics we've ever seen with his Wheel of Worry, which revealed that while falling asleep he frets about loneliness and the New York Knicks in almost equal proportions. Try this one with a book-group member you've never quite connected with: What oddball worry would most color your Wheel of Worry? Share a bit of yourself—and yes, this involves making yourself a little vulnerable—and you'll be surprised at how people all around will cleave to you. Trust me. I had a conversation that began, "I know, I always think I'm going to get walked in on in public restrooms, too!," and bloomed into an entire friendship.
7. Speak Her Language.
If you're in France, you need to speak a little French—even if it's only to say please and thank you, and to not be the "TALK ENGLISH?" traveler. If you're on the PTA committee to raise funds for the school, you have to know what all those DOE abbreviations are, and learn how to talk so the Board of Regents will listen. Communications coach John Artise told O magazine that there are four basic kinds of communicators: Feelers, Sensors, Intuitors and Thinkers. Notice how the person you're talking to operates (for example, the bossy PTA committee chair who talks a mile a minute and then gets annoyed when you ask her questions) and attempt to mirror her style (She's an intuitor and thinks you know what she's talking about, so let her speak for a while before asking your questions). She'll likely feel more understood, and thus more like opening up to you.
8. Assign the 2 of You to a Minimission.
When you're naturally on the shy side, as I am, you're constantly worried about annoying people, which you seek to avoid by talking as little as possible. But people sense when you feel uncomfortable and it makes them uncomfortable, which starts the whole toe-staring, blushing cycle anew. Here's a shy-person trick from the trenches: Invite someone to be your sidekick on a minimission. Enlist someone else at the church coffee-hour to accompany you to pick up an extra box of cookies when the refreshments are running low, and your shared purpose will bring you together.
9. Ask Someone Else About Her X-ray Vision.
Sounds crazy, I know, but sometimes the best way to get to know someone is not to talk to her at all. At a dinner party, you might say, "So you two have been friends since high school? What's her superpower?" Ask the friend of the person you want to coax out of her shell—being flattered will relax her, and give her something specific to talk about. Even if it's just, "Oh no, I’m so NOT a superstealth scarf knitter, maybe a social-setting shapeshifter though…"