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When a woman is talking to you, listen to what she says with her eyes.”–Victor Hugo

The thing is, for women, guys can be scary. Especially if our interest is not wanted. We come across as creepy jackasses, indifferent to the emotions of another person. Which, yes, I know, is not our intent. But we still can come off this way. You can be a guy who cuddles bunnies and gives his life savings to the poor and feeds hummingbirds from your bare hands and be the most wonderfully nice guy ever in the history of the universe, but if you approach someone who does not want to be approached, that makes you creepy. If you do something that makes another uncomfortable, that’s creepy.

This doesn’t mean you have to be timid around women. But it is a fine balancing act. In fact, learning what boundaries are normal for women is a really good reason to gain some female friends. They can teach you what you might be doing wrong. But here’s a general rule: most women I know do NOT like being accosted on the street, or in the bus, or on the train by men they don’t know.

If you cross someone’s boundaries, that’s coming off as creepy, even if you have the best of intentions. A true gentleman should keep this in mind.

Sidenote: it’s worthy to note that sometimes, women can come off as creepy, and this is not a feeling to be ignored in the slightest. A few months ago, after barely messaging a woman on a dating site, I was emailed with a four-page work that essentially amounted to a manifesto, detailing… a lot of strange things that shouldn’t be discussed until after engagement, really, and what she had analyzed it all to mean. In a word, very creepy, as it crossed an entire host of boundaries, both personal, and I feel social as well. If someone creeps YOU out, regardless of gender or age, back away.

Here’s the key of creepiness: if you’re creepy, you’re in a position where you do not have emotional permission to do such a thing as was requestedThe woman who messaged me had no emotional permission to demand of me that I shave my armpits so that she’d know I was “thinking of her,” let alone emailing me a manifesto.


Q: You see a woman with headphones, with her nose in a book, on the Boston T. The book is your favorite book in the world. What do you do?

A: Don’t talk to her. She’s in a “no-talking” zone. Anything you do to make contact might be seen as harassment, and will likely be seen as creepy. (That being said, if you see someone else harassing said woman, do speak up on her behalf. All you need to do is say, “Hey, leave her alone, she’s obviously reading.” or the like. Do not expect anything more than a curt nod as thanks, but at the very least, you will have done a good deed for the day. And even if she doesn’t say thanks, she will likely be grateful. Just be sure to back off after you’ve done your duty as a gentleman. Saving her from a creep doesn’t entitle you to anything.)

Actually, here’s an aside speaking of entitlement, I noticed that a lot of single men felt “entitled” to a wife. That it was their reward for years of duty, or something. Here’s a sobering fact: We men are not entitled to anything involving a woman. And it is naive and prideful for us to assume that God has a wife lined up for us. Here’s another sobering fact: you won’t be in a successful relationship until you’re comfortable with being alone with yourself—after all—if you don’t like being with yourself, why would your hypothetical significant other? So knock that prideful attitude off, it’s getting your nowhere. Remember: Humility, patience, and thoughtful speech are the keys of being a gentleman.

That being said, if the woman has no headphones, a simple “I love that book, it’s my favorite,” will do as a polite conversation starterIt gives the woman an option of gauging several things, namely: is this person potentially threatening. It’s directed at the book, not at her. She can either reply with curt “uh-huh,” (in which case, leave her be, as any further interaction might constitute creepiness in her eyes, just nod, smile, and walk away. She either does not want to be interrupted, or is angry, or is afraid. Respect the distance, if the distance is there. Do not override her signals. Don’t try to convince her to talk to you if she doesn’t want to talk to you. You don’t have the right to put yourself in that position if she does not want you there, so back off.)

Or an exuberant “Really? I like this book too. The way that Tolkien describes the Rohan steppes reminds me of the frigid wastes of Wyoming where I grew up, and makes me a little homesick.” (In which case, congratulations, you met one of the five people who grew up in Wyoming. Also, a response like that is a general indication that she’s willing to converse with you. Sit and chat for a bit. You will likely have made a new friend. Don’t assume anything more than that until evidence contrary to that assumption exists.)

Here’s another piece of advice that I follow: don’t assume you’re going to end up dating any given woman you talk to. Assume friendship. It’s less threatening, for one, and for two, you won’t go into anything with the objective of courtship in mind right off the bat—which is always dangerous.

The key is to relax. Be comfortable with yourself, and know societal boundariesOnce you know boundaries, and can read body language and signals, you’re more than halfway there. Remember that this woman who you want to get to know is a person, not an object, with her own history, flaws, hopes, and dreams, and fears. Just as you are your own person with your own history, flaws, hopes, dreams, and fears. It’s funny how that works.

Lastly, here’s two links from orthogals, on creepyness. Read them, too, for a woman’s perspective on the same issue. They’re pretty awesome. (The links, though the bloggers are pretty chill as well.)



Next up: any port in a storm.