How to Meet that Attractive Stranger

how to meet a strangerInsightful author Sara Eckel returns with her latest guest blog. This time it is about the art of approaching a stranger — not the easiest thing to do.

It’s the stuff that the “Missed Connections” sections are made of.

You see a person — reading a novel at the airport, folding t-shirts at the laundromat, pressing the “up” button in the elevator bank. You feel drawn to their quiet energy or crooked smile. You want to introduce yourself, find out if they’re single (left hand checks out!), and ask if perhaps they’d like to meet you for coffee later.

But how? Asking these questions out of the blue seems weird. Even if the other person is interested, they may be too freaked to say yes. Mom told us not to talk to strangers. But Debra Fine, author of The Fine Art of Small Talk, says there are ways to approach people without looking like a stalker.

1) The Opener

The point of an opener is not to state how wildly attractive you think this person is — awkward! It’s simply to say, I’ve noticed that you’re a human person. I’m a human person too.

Ask a simple, neutral question. “Base it on free information about the occasion or the location,” says Fine. For example, if you see a cute guy sitting alone in a coffee shop, ask if he knows how long it’s been open. If he has the answer, he might be able to give you more information about the cafe, the neighborhood, the crowd, etc. If he says “I don’t know. I’m not from around here,” well then there’s the topic.

Enlist help. If you ask a cute guy to watch your bags or laptop while you step away, you’re letting him know that you think he’s trustworthy—people like being considered trustworthy. You can further extend the gesture of friendship by asking if you can get him anything while you’re up — coffee, soda? When you get back, you’re already pals so asking about his book or smartphone is only natural.

2) Keep Talking

Once the pretty girl on the bus confirms that it does indeed stop on Cranberry Street, you need to find a way to keep the conversation going.

Asking questions usually gets people taking, but you don’t want to pry. “Don’t play FBI agent,” says Fine. Instead, offer a little bit of information, followed by a question on that topic. For example: “I’m going to the new park that the city just opened. Have you seen it?”

At this point, your natural good sense will tell you whether or not she wants to engage with you or go back to her e-reader. But even if the answer is, “No, I’ve never heard of it,” there is still room to keep going. “A friend told me it has walking paths along the river and a great Mexican food truck. I really love just wandering around on a Saturday afternoon. What about you?”

A statement like this does two things — it drops a major hint in the guise of neutral information. It also gives the other person a chance to engage without putting anyone on the spot. You didn’t ask “Where are you headed?” — which can sound vaguely stalker-ish. You’re just finding out whether a Saturday afternoon in the park is something she might hypothetically enjoy.

The ultimate goal is not to get the attractive person to go on a date with you — it’s to give her the opportunity to express interest if it’s there. If she says, “Hope you enjoy your day!” or “Oh, thanks. I’m going to take my boyfriend there” then you have your answer. On the other hand, if you hear, “Wow, that’s my favorite kind of Saturday, too!” then it’s time to suck it up and suggest you go together sometime.

Of course, you could still hear no. But it beats writing a Missed Connections ad.

Do you have a way you are most comfortable when it comes to approaching someone you might be interested in?

its not you sara eckel

About the Author:

Sara Eckel is the author of It’s Not You: 27 (Wrong) Reasons You’re Single. You can get a free bonus chapter of her book at You can also find her on Twitter and Facebook.

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