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Cora Considers Meeting In The Wild


With increased awareness around the ubiquity of sexual harassment, the male population is rightfully feeling more circumspect about treating women in a way that makes them feel safe and respected. Over the past couple of years, I’ve received the following question from male clients and friends with greater frequency:

Is it possible to approach women you don’t know in public without being creepy or crossing a line?

My answer to this question is a resounding yes!

Being open to the possibility of meeting someone out in the real world, not just online or at a function where it’s socially sanctioned to start conversations with people you don’t know (like a conference or a party), is a great way to claim some agency in your love life.

When it comes to meeting romantic prospects, we can either hand our agency away to circumstance and wait around for someone to knock on our door asking if we want to go to Burger King, or consciously create opportunities for connection every day.  We cross paths with interesting people everywhere, and it is absolutely possible to meet someone in any context, whether it be the grocery store, the dentist’s office, or the dog park.

That being said, no stranger owes you a conversation.

Said stranger could be in a relationship, not interested, or simply not in the mood to engage. It is paramount to respect this and know when to walk away.  When putting out feelers for connection, some fish will bite and some won’t. But you’re not going to meet anyone new if you never cast the line.

Here are best practices for how to respectfully approach not only women, but any person-of-romantic-interest out in the wild:

1. Drop your expectations and be friendly.

The best way to get comfortable talking to strangers is to flex your friendly muscle and get in the habit of chatting with all kinds of people in your day-to-day life, regardless of whether or not you are attracted to them.  Our expectation for results is the only reason that making a croissant joke to the cutie next to you in the Starbucks line is more intimidating than telling an old lady at the bus stop that you like her loafers. So when making said croissant joke to said Starbucks cutie, aim for nothing beyond a pleasant interaction with another human, and let yourself be pleasantly surprised if it seems like she wants to keep talking.

2. Be mindful of the circumstances.

If you’re going to test the waters with an attractive stranger, take note of your location, the circumstances, and what they’re doing.  From a hetero-persepctive, put yourself in her shoes for a moment and consider whether engagement from a man she doesn’t know would feel safe or welcome. The most important thing is that she feels she has a choice if she wants to talk to you or not.

If she’s alone at night, or if you’re in an enclosed space with no escape route, like an elevator, leave her alone.

And if she has headphones in, is reading, or appears to be focused on what she’s doing, let the woman be.  She’s probably building her empire and doesn’t want an interruption.

3. Say something open ended and let her respond.  

When it comes to what to say, steer clear of making comments about her body or her looks. This can feel objectifying and threatening. Beyond that, what you actually say isn’t crucial:

  • Tell her her her purse is great.

  • Ask her how she’s doing.

  • Ask her for directions.

  • Ask her where the best breweries are in the neighborhood.

  • Ask her for her opinion on something.

If she’s not interested in talking, she’ll respond curtly and you’ll both move on. Remember: it is absolutely her prerogative to not want to talk to you, or anyone at all. If, however, she is interested, you’ve created an opportunity for her to reciprocate and let a conversation unfold.

4. Give her your number instead of asking for hers.

In the event that she does want to talk and you two hit it off, keep the conversation to a few minutes and then offer her your number instead of asking for hers. This way the ball is in her court, and if she reaches out to you, it will be her choice.

So go out into the world and meet some people.  Put your feelers out and see who responds.

Remember that you never know what is going on in someone else’s life, so do your best not to take it personally if someone doesn’t want to talk to you.

The only risk in being friendly is that you get shut down and feel a little foolish for a total of five minutes. But the reward, if you’re respectful, warm, and ensure that she always has the choice to walk away or disengage, is that you could make her day, remind her of the good in this world, or even meet the love of your life.

In addition to matchmaking, Cora offers one-on-one date coaching for men! Learn more about her work, here.

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