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Operation Charisma: How to Talk to That Cute Guy or Girl With Total Confidence

How many times have you passed up the opportunity to talk to a stranger, held back by a fear of rejection?
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I spotted him at 1 o'clock on Metro North on the way to Grand Central Station in New York City. He had the looks of Orlando Bloom. Those deep, focused eyes and fine lips. Auburn hair. He was listening to music on his iPod. And I really wanted to get to know him.

After "thinking about it" for 20 minutes (read: being scared), I finally took a deep breath, asked the person next to me to let me out of the seat, casually walked up to my target, smiled, and said, "Hey, how's it goin'?"

What ensued was a fun 15 minute conversation. I learned that he was going into the city for an interview for a physical trainer position at a gym. He had grown up and went to school in Connecticut. I also got his name (but didn't ask for his number... he was a bit young for me).

Chatting with attractive strangers has been a long-time phobia of mine. As a single lady looking for love, I'll hear stuff like "Women shouldn't approach men first," and so I've had few results when it comes to meeting new people. This attitude cost me several promising budding relationships where I couldn't make eye contact with my love interests at parties because I felt I should have been sought out first. Even at Argentine tango social dances, where eye contact is a form of an invitation to dance, I struggled with this. Because I couldn't master the eye contact thing, I ended up sitting out at a lot of the dances and feeling crummy about it, even though I desperately wanted to dance.

But if you think about it, in-person social networking is like a dance that begins with a glance. How many times have you passed up the opportunity to talk to a stranger, held back by a fear of rejection? Most of us don't engage because 1.) It's stressful to approach a stranger, inducing as much anxiety as public speaking or asking the boss for time off 2.) We risk rejection and the status quo is less painful and 3.) We're never going to see them again, so what's the point?

Benefits of chatting up strangers are several-fold: You'll be better at networking, be more fun at parties, be more confident to ask for those big-time assignments on the job and be more confident in general. I'm all about getting you in touch with your inner awesome so that you can experience all the above!

So, how did I manage to walk up to my Orlando Bloom look-alike and have an awesome conversation? I've been able to do this only after intentional practice and going on what my friend Nicholas and I call "Operation Charisma." This is how Operation Charisma works: Once a week on a Saturday, we go to a public place, like the Barnes and Noble, Apple Store or coffee shop, and we chat up attractive strangers. Here are some steps to help you do just that!

Step 1: Find a face that you are attracted to.
This will be an incentive to keep the conversation going. People are like tuning forks: If you are interested and enthusiastic, the more likely they are to show interest in you, too. If you're not at least superficially connected to the person at first, it will be more difficult (but not impossible) to establish a connection.

Step 2: Go up to them and smile at their eyes.
Yes, actually look into their eyes and smile. Then start with a, "Hi how's it going?" while actually caring about how they are doing. At this stage, it's normal if the person looks surprised, because we're rarely accosted by smiling strangers who want to get to know us, right?

Step 3: Be curious
Ask open-ended questions and build on it. Use the situation to your advantage. Ask questions about what books they're looking for, what they do, but most importantly, ask about their personal experiences. Oh, they're from around the area? What is it like to live there? Actually be interested in knowing their experience.

Begin with the end in mind
For Nicholas and me, our goal was to know the names of the persons we were meeting. If we got a name, that was a success for us. When we got comfortable and fairly successful with this after week three, we upped the ante to asking for phone numbers. The priority was always having an engaging conversation. With one particular person (a security guard at Barnes and Noble), I had such an engaging conversation that lasted for 15 minutes that I forgot to get his phone number. But as I left the store, he was waiting by the checkout counter to hand me a piece of paper with his number written on it! BOOM!

Feel the fear and do it anyway.
This is a very stressful activity because we think we know what the person will think of us (She's such a weirdo! She's desperate. Huh?), but the more you do it, the more you find that the worst that happens is that people aren't interested in having a conversation. That doesn't mean they're not interested in you, but that they may not be open to it as you are. And that's OK. The point of doing this is to open yourself up so that when the right person comes along, you're ready. It's through continual rejection that we strengthen self-acceptance.

That's it! These are really simple tips, but really hard to do because almost no one does this. The first few rejections are really tough, and that's why going with a support buddy really helps. When Nicholas and I go, we take turns and the one who's not doing the talking will watch unobtrusively in the background and observe. When we wrap up the conversation, we have a private powwow to talk about what went well and what could have been done better. After doing this with 3-5 people each, we're on such an emotional high.

Interestingly, going on Operation Charisma on a regular basis has made it easier for me to express myself effectively and communicate my boundaries with others. The more interactions you have, the less importance you place on a single one, and so any anxiety that comes with owning your voice and asking for what you want melts away. When you realize this, you project a natural confidence which attracts more opportunities for personal or professional relationships.

So, what are you waiting for? Go out and talk to an attractive stranger today! If you can do this, you can do almost anything!

Catherine Chen, Ph.D., is a Health Coach who believes that you are important, no matter what you achieve. She works with high-achievers to move past the guilt, frustration and overwhelm to have the career and life they want. Sign up here to get a video series on finding your awesome at

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