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Speak Her Language
Communications coach John Artise says 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 church leadership 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.
Embark on a Mini Mission
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 mini mission. Enlist someone else at the PTA meeting 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.
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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.
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Ask Someone Else About Her Hidden Talent
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 secret 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..."
Amy Shearn is the author of How Far Is the Ocean from Here? and The Mermaid of Brooklyn: A Novel.
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 your 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.
Ask About His Last All-Nighter
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.
