Photo by Adam Zvanovec on Unsplash

How To Talk To A Woman

Bulletproof advice for fellas.


You’ve probably seen it by now — that YouTube vid that careens through 10 painstaking hours of walking through NYC as a woman. In it, she — all while avoiding eye contact — runs a gauntlet of come-ons, creepings, catcalls and conversation non-starters. A lot of them say “hello” or call her “beautiful.” I dare you to watch it without wincing.

You might be saying to yourself, “Well … I don’t see what’s so bad about saying hello or paying a compliment.” I think that’s a valid point and one worth addressing. We’ll do so here.


In one-on one conversation, there are two parties: The initiator (the one who starts the conversation) and the receptor (the one who needs to choose whether to engage or ignore the initiation). When men approach women — with a hello, or a compliment, or a subtle “Dammmmmmn grrrrrrrrl” — they are initiating. Now the burden is on the woman to address it. There are times when men approach women in such an over-the-top fashion that women are left with no choice but to engage. This is, obviously, problematic. Now there are expectations placed upon a woman without her consent. That’s the first issue with saying hello or paying an unsolicited compliment.

The second issue revolves around the past informing the present. Often times, men who approach women in a seemingly innocuous fashion are viewed unfavorably, because quite often, other fellas before them have lobbed the same friendly “Hello” like a grenade — a grenade which later explodes into unwarranted sexual advances and uncomfortable flirting. Because of this, any man who assumes the role of initiator will be viewed as “that guy.” If you take nothing else away from this column, it’s this: Don’t be “that guy.”


Women don’t have time to deal with whatever shit you may or may not throw at them, and they sure as hell don’t have time to decide whether or not you may or may not throw shit their way. Ignoring your advances is nothing personal: It’s merely an algorithm they’ve developed that helps them mitigate risk. It’s not all that dissimilar to locking your door at night or changing the channel the minute you hear the words “LaVar Ball.”

So if you can try viewing the interaction through that lens, you can see that women are probably pretty tired of having to fend off initiators with silence, strength and occasionally spray. Now that you know, now you don’t have to drive women panda-shit insane on comment threads, asking for a hard, fast man/woman interaction code of ethics some 472 pages thick … like these enterprising young Romeos did:

When did a man saying anything to a woman in public become a “catcall”?
If you are interested in approaching someone you are attracted to, must you also approach everyone else, so the person you’re attracted to doesn’t get the wrong idea?
Why does finding someone attractive and wanting to say “hello” to them have “sexual undertones”? Why is wanting to strike up a conversation with someone you find attractive a bad intention?
Why automatically assume it to be “catcalling” or sexual harassment?
How would someone who finds another person attractive initiate contact with that person? If “hello,” with no follow up if ignored, crosses the line into catcalling and harassment, what wouldn’t be catcalling or harassment?

Yikes. Sit this one out slugger. Let me help you.


As established earlier, women get to choose who they wish to interact with moment-to-moment, day-to-day. Until you receive a very, very clear signal that they wish to engage you, (like a “hello” or a warm unsolicited smile), then they have not selected you for a speaking role in that scene. You’re an extra. Speak when spoken to — and, yes, sometimes that speaking is non-verbal. Listen with your eyes. Let’s open it up for questions.

Q: What if I want to talk to a woman and she says nothing?

Maybe she spilled coffee on her favorite shirt that morning. Maybe she’s really digging this episode of “All Songs Considered.” Maybe she’s pissed at her boss. Maybe you’re wearing cargo shorts. In any case … that’s not your concern. You can move on. Someone, somewhere, will say hello to you first.

Q: What if a lot of women say nothing to me?

Find a way to be interesting. Read a new book. Listen to a new podcast. Take a Portuguese language immersion class. Cook a mean pad thai. Start cross-fit. Get your dream job. Go to grad school. Invite your friends to a whiskey tasting. Mentor some kids. Walk shelter dogs. Backpack through Asia. Meditate. Brew a tasty IPA. Bike across town. Pick up a guitar. Paint the skyline. Create. Make. Do. Share. Experience. Oh … and stop wearing cargo shorts.

Q: What if I do all those things already and no women give me the green light to say ‘hi?’

You’re a liar. Or you have a face tattoo.