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How to Flirt with a Woman

Here are some easy steps to get you started.

If you’re a single and struggling gentleman, Professor Menelaos Apostolou, Associate Professor of Evolutionary Psychology at the University of Nicosia, thinks it might because your social skills haven’t evolved enough.

Think about it: for thousands of years, mating, and then marriage were, in many ways, arranged. As cavepeople, women mated with the strongest men that could be counted on to provide food and protect their families.

Then as societies industrialized but women’s access to jobs remained limited, they chose mates that could financially provide for them.

For centuries, inept, awkward, or just plain awful men had no problem finding mates because the bar for them was so low. Man can get meat. Man can make money. Man can get mate.

Well, times have changed. Women can take care of themselves, and they no longer need a “provider” as much as a “companion.” That’s a huge shift.

Professor Apostolou states, “men who have difficulty flirting…may remain single because their social skills have not evolved to meet today’s societal demands.”

When I was dating, I matched with a few men that were helpless in the conversation department. They said outrightly sexual things too quickly or just wanted to talk about themselves (or Norse Mythology in the case of one guy). Some men seemed great when we were just messaging, but then they wouldn’t even look me in the eye when we met in person.

If you know you struggle with flirting, you might be inclined to hate the ways of the world today, but then you’d just be wasting your time. Society is marching toward gender equality, not away from it, and the sooner you can get on board, the sooner you can quit moaning over the state of your love life.

If you find yourself lagging in the flirting department, here are some tips for how to improve your game:

1. Look approachable. Do you have Resting Asshole Face or just generally walk around scowling? Do you keep your arms folded in front of your chest? Do you ignore whenever someone tries to chat with you pleasantly?

If you’re wanting to be approached or to generally look less terrifying, pay attention to how you hold your body.


Look people in the eye.

Keep your arms at your side instead of crossed in front of your chest, and respond to the pleasantries even if it’s to say, “Yup.” or “I know, right?”

Your body language will influence how someone reacts/responds to a conversation with you.

2. Take it easy. If you look up the definition for “to flirt,” it is, “to behave as though attracted to or trying to attract someone, but for amusement rather than with serious intentions.”

Flirting is an initial conversation or some witty banter; it’s not the speech you prepare for when you ask her to marry you. Try to think of it as a very low-stakes game.

Women aren’t going to eat your face if you attempt to flirt with them. As long as you’re respectful, the worst you might get is an eye roll. Further, your failure to get a woman’s number or a second date with her isn’t a direct sign that you should be single forever and go set yourself on fire.

Don’t put a lot of stock into your attempts. Just enjoy talking with someone, and leave it at that.

3. Walk the line. Most women are turned off by presentations of male extremes. You should neither act or speak like you’re doing her a favor by talking to her nor that you don’t deserve to talk to her.

Treat her like your equal since acting like a cocky asshole won’t likely get you anywhere. She’s a person with her own strengths and weaknesses just like you.

Also make sure to show respect for yourself by not spending too much time putting yourself down. If you don’t like yourself (or come off that way by making more than two self-deprecating jokes), she probably won’t like you either.

4. Tease her.

Playful teasing is often a good way to begin flirting.

If you see order a certain kind of drink, lean over and tell her, “You ordered that? Not sure we can ever be friends now.”

Make sure to keep whatever you say light and follow it with a smile, so it’s clear to her that you’re joking.

Don’t get too personal either, since that might veer too close to “negging” territory. Urban Dictionary defines “negging” as “low-grade insults meant to undermine the self-confidence of a woman.”

Think of these as back-handed compliments: “You look great. Not many women would have the courage to wear something like that.” “Your calves are flabby, but I think they’re cute.” Assholes neg. Decent people lightly tease.


Women want men who will listen and participate.

In one study, sensitivity (defined as being compassionate, kind, able to share and discuss feelings) was the second most desired characteristic in a long-term partner by women.

Gone are the days when surly sullen men were what’s hot. Women now want a teammate, not a good-looking mute.

An easy way to practice actively listening is to use the acronym SLANT:

S: Sit up L: Lean forward A: Ask and answer questions N: Nod your head yes or no T: Track the speaker (following them with your eyes and body)

Doing all of these will help her feel heard and also ensure that you’re not missing out on something important. You definitely don’t want to make the mistake of taking her to Golden Corral when she clearly told you how much she hates buffets.

Women don’t want to be put on a pedestal nor to be treated like the trash you take to the curb every week. They want you to see them as human. Therefore, treat your flirting like a nice casual conversation with someone you happen to find attractive. Don’t get too attached to the outcome, and see every opportunity to flirt as a chance to improve.

Don’t neglect, too, that women want more sensitive dudes as long-term mates, so sit up, listen, and be courteous.

Lastly, don’t forget how awesome you are. You’re a lovable, cool dude. Avoid undermining yourself or overcompensating by being a jerk. Dating is a game, but it’s one you can’t win if you don’t play.

Want to have a better relationship today? Click here to sign up for my FREE “Being a Match for Your Dream Relationship” Worksheet!

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