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8 Tips For Approaching Anyone, Anywhere, Anytime

Land a girlfriend, nail an interview, meet mentors and find job opportunities with these tips from the masterminds behind the Art of Charm.
8 Tips For Approaching Anyone, Anywhere, Anytime

If there’s one skill that will catapult you in work, love and life, it’s the ability to walk up to anyone, anywhere, anytime, and form a new relationship. I’m willing to bet that the urge to approach someone newa cute girl on the street, a professional hero at a conference, or a dude at a cafe who seems like he’d be a cool friendstruck you at least once this week. I’m also willing to bet that you let at least one of those moments pass, and decided not to take the leap.

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That’s perfectly normal. Approaching a stranger holds all sorts of exciting possibilities: connection, trust, validation. It also holds all of the terrifying risks: discomfort, mistrust, rejection. Evolutionarily, there’s a good reason for this. It can be risky to get outside of your established tribe (a hangover from our caveman days), while staying in your comfort zone guarantees your safety. Let’s be honest: Other people can be scary!

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And yet approaching a stranger can literally change your life. Across the 5,000+ students we’ve coached at The Art of Charm, we’ve seen guys land girlfriends, secure interviews, meet mentors, find job opportunities and build a rocking social network by working through their fear of talking to strangers. If you can master this anxiety, and recognize how and when to approach someone new, you’ll quickly find your world opening up in ways you never imagined.

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So, here are 8 ways to conquer your fear and master the art of approaching a stranger.

I’d estimate that 90 percent of approaches fail because people miss—or, even worse, choose to ignore—an opportunity to meet someone new. When the world serves you up a chance to connect with someone, pay attention. It usually means you should take it.

Generally speaking, the signs are pretty mundane. A girl will stand a little too close to you at a bar. A speaker will have a free moment at a conference. You’ll walk by someone reading an interesting book. You won’t get grand signs from the universe telling you to approach, just simple openings for you to walk over and say hello.

So take them! You’d be amazed at how many opportunities you have when you start paying attention and embracing them. All great approaches begin with that simple step.

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Let’s not pretend that approaching people is easy. To this day, having approached thousands of people in my life, I still get that telltale flutter when I approach someone I like. That evolutionary wiring runs deep.

So I won’t tell you to “master your fear” or “embrace the risk”that would be like telling you to be taller. Instead, accept that you have the fear, and acknowledge the risks. That alone will dramatically reduce the sensation of fear. Another great way to cut through the anxiety is to ask yourself: What’s the worst that can happen? Rarely do our worst fears pan out. At the very least, you’ll learn something about yourself, and get that much better at approaching.

Remember that great approaches don’t come from total confidence. They come from a genuine acceptance of your fear, and a willingness to say hello despite it. Your fear doesn’t make you weak; it makes you human. And humans love meeting other humans.

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A great excuse to not approach someone is that it just wouldn’t be “appropriate.” Now, it’s true that there are bad moments to approach—when someone’s on the phone, for example, or clearly on a date with someone she likes.

But generally speaking, what your mind calls “inappropriate” just means “not served up on a silver platter.” In fact, I’d say that most interesting people will be a little hard to reach. Your job isn’t to be perfectly “appropriate,” but to break social norms in an appropriate way.

So walk over to that girl having drinks with her friends. Ask that writer for five minutes of his time. Say hello to that guy having breakfast alone. Be kind, courteous, and to the point. Worst-case scenario: You come across as a little random. Best-case scenario: You put yourself in a situation to form a new relationship.

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This might be the most nuts-and-bolts piece of advice I can offer on approaching. In a world filled with weirdos, psychopaths and people who always want something from you (and trust me, most girls are conditioned to expect guys to fit into one of those categories), it’s your job to establish that you are normal as quickly as possible.

You do this with every step you take. With the way you approachkindly, gently, patiently. With your body languageconfident and open. With what you say“Hey, I’m sorry to bother you while you’re having breakfast, but you seem cool and I wanted to say hello.” Together, these paint a picture of you as safe, stable and normal.

Every successful approach requires the other person to feel that you can be trusted. Bad approaches, even from good guys, usually happen when the other person suspects that there’s a hidden agenda or an undesirable intention. Remember: As long as you seem safe and normal, it’s difficult to do anything wrongeven if your approach doesn’t go anywhere, and even when your instincts tell you otherwise.

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On a related note, building rapport is one of the fastest ways to create trust with someone new.

But contrary to common thought, building rapport isn’t about looking for one-to-one commonalities with the other person. For example, a guy who immediately talks about losing his labrador when a girl mentions her terrier will usually come across as overly ingratiating and self-centered. The key, as we teach on day one of our residential program, is to find the common experience. “It sounds like you and your dog were really close. That’s how I felt when I adopted my tabby—changed my life. Pets are the best, aren’t they?” That is the stuff of real connection, not surface-level commonality.

Another good way to build trust is to find common connections. If you run in the same circles, attended the same schools or share similar hobbies, then mentioning those will signal that you come from the same tribe. (Again, evolution, man.) No need to pimp those out like the labrador story, and don’t worry if you don’t have any mutual connections. Just look for different opportunities to create trust, especially at the beginning, because it will pave the runway for you to continue talking.

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Popular social dynamics theory will tell you not to pay compliments, especially to women and especially early on, because doing so will either come across as needy or imply a lower social status. That might be true in many cases, but it’s not because of the compliment. It’s about the intention behind the compliment.

When you find yourself wanting to compliment someonewhether it’s your literary hero or the girl at the barask yourself why. Are you trying to ingratiate yourself? Flatter your way in? Or do you genuinely want the other person to know how much you like them?

If your compliment is genuine, then it’s usually safe to shareeven with a stranger. The reason is that if you actually mean it, then your compliment will come across as confident, kind and matter of fact, rather than hollow or manipulative. I routinely tell the people I admire how much I enjoy their work. My students regularly tell girls they meet how much they like their hair, their outfits, the way they speak. These are all acceptable compliments because we mean them.

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If you’re going to approach strangers, then you must be versed in non-verbal communication. That means you should begin studying body language and the subtext of conversation.

Remember: The most interesting things go unsaid. If a girl turns toward you at a bar and continues the conversation, she’s implicitly letting you know that you can continue talking. If she doesn’t make eye contact and turns back to her group, it’s probably time to move on. Similarly, a hiring manager who’s checking his email is probably not too keen on hiring you, but the manager who hangs around with you is taking time out of his day to get to know you.

Oftentimes, these cues can be more subtle: a flash in someone’s eye, a poignant follow-up question, a lingering handshake, a willingness to put down a book and talk to you. Study these cues, and use them to calibrate your approaches. People will generally tell you whether they are vibing with your approach. Your job is to listen, and act accordingly.

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Every successful approach will result in a plan to connect later on. No matter how well you come across in your first meeting, you’ll always have to follow up in some wayby phone, text, email or social.

There’s no magic formula here. You simply have to commit to following up. That might seem obvious, but you’d be amazed how many guys fail to do it. They meet a prospective employer, and never set up a phone call to discuss the job. They meet a cool girl, then let days or weeks pass without saying hello. There’s no excuse for it, really. If you’re going to approach, then go all the way, and continue building the relationship.

Otherwise, you’re missing out on all the rewards for taking the chance and approaching a stranger.

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