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How to Flirt

Learn to Flirt Like a Pro by Following This Simple Guide

April 6, 2023

Flip

Most of us would like to be better at flirting. It seems as though the most expert flirters among us mingle effortlessly with the opposite sex (or whoever they're attracted to), while most of us blush, stumble over our words and generally fail to make an impression. Flirting requires a few key ingredients blended to perfection, including confidence, wit, flattery and respect, but often it seems like a gargantuan task to work up the nerve to talk to a woman, let alone seal the deal by charming her.

This difficulty helps to explain the meteoric rise of the self-styled pickup artist culture in the 2010s, which encouraged shy and/or nerdy men to approach women by providing a few paint-by-numbers rules for gaining their attention.

Unfortunately, these rules were typically based on shredding the self-esteem of the woman you’re flirting with, who is usually selected simply because she’s “a ten” (as in, scores 10/10 for looks.) The aim is to “neg” these women to bring them down a peg — issuing a kind of backhanded compliment calculated to unsettle her and make her insecure, and thus more grateful for your attention.

This is an awful way to think about women, relationships and yourself. Pick up artists rely on an outmoded, market-based and sexist model of gender relations, and use unethical and ultimately ineffective strategies.

Yet some pickup artists’ strategies remain popular to this day because they tap into a desperate need for many men to find a way to confidently approach women. What we need, then, is an approach to flirting that contains some of the (few) useful ideas from pick up artist culture, but which isn't antisocial and rooted in damaging ideas about women and dating.

Behold, then, some kinder, more effective flirting tips for the modern gentleman who doesn't condescend to or fear women, but would like to be better at flirting with them.

Let's break it down:

What Is Flirting?

In the simplest possible terms, flirting is usually a form of conversation that reveals a sexual or romantic attraction to another person, but which is lighthearted rather than serious in tone. It's usually the first step to elevating a platonic relationship into a romantic one, or to signal a romantic intention right off the bat.

Two of the best flirters in the game face off against each other.

Flirting can be done in lots of different ways — in person, over texts or DMs, via emails or letters, and more. While it's often primarily a case of using your words, it can also involve body language or gestures and, in some cases, physical touch.

It's often an activity that occurs in a kind of excited mental state — when it's going well, the rest of the world can melt away and all that's left is you and the person you're flirting with. But it can also be super awkward when your jokes don't land, or the other person doesn't seem to be vibing with you — at which point it's best to beat a hasty retreat.

Flirting can sometimes be mistaken for simple politeness, or vice-versa. Charismatic and charming people may seem like they're flirting with everyone they talk to; the line between casual flirtation and genuine attraction can be blurry and shift depending on one's perception.

But while flirtation can be mysterious and hard to pin down, it very much does exist. Want to get better at it? Keep reading.

Basic Flirting Tips

To be good at flirting, and to engineer situations in which flirting is likely to be maximally effective, it’s important to consider the following points:

Choose the Right Environment

It's perfectly appropriate to flirt with single people in social environments where romantic approaches are customary, for example in bars and at parties. Of course, flirting on dating apps such as Tinder is appropriate, too.

However, there are other circumstances where flirting is not appropriate and should generally not be initiated. Flirting at work is never appropriate if you are in a position of power over your coworker (for example, if you are her boss), and in general you should not try to flirt with a co-worker during work hours — she’s trying to be professional!

Situations when women are trying to go about their daily business, such as at the gym or on the bus or train, are not great times to approach her, either, as they are likely to be received as an annoyance rather than a compliment.

Work to Your Own Strengths

Lots of us would love to have Don Draper-levels of effortless charm, but if you're naturally a bit more goofy or shy than the smooth 1960s Mad Men (and women), forcing this persona is not going to work.

Besides, it's unnecessary. Plenty of women prefer down-to-earth, funny and self-deprecating men and find the calculated slickness of more traditional flirters off-putting, so make sure that you’re flirting in a way that's natural to you and compatible with your personality type.

RELATED: Dating Tips for Shy Guys

Shyness doesn't preclude you from having a successful flirting encounter. If you are shy, you will clearly have to build up the nerve to approach women — almost everyone finds this part somewhat difficult, by the way, even if they don't seem to!

Fear not, though, because plenty of women find shy men endearing. Michael Cera is often used as a go-to example of an inept flirter — someone who’s hopelessly awkward and clueless with women — but some of my most dateable friends find find him irresistible. Somebody out there is bound to find your specific personality quirks endearing, so go for a funny, offbeat approach if that’s more your thing, rather than faking it.

Pay Attention to Body Language

Flirting is an exercise that takes place non-verbally as well as verbally, so pay close attention to touch, body language and positioning. Often, women will signal that they’re interested in being approached in subtle, non-verbal ways: by smiling, touching you or their hair, or positioning themselves closer to you, for example. Don’t be oblivious to these signs, as they will give you crucial information about how well your encounter is going.

He’s waited for a sign she's interested (“I see you glassin’ me, that's why I'm asking, B”); he's landed a few genuine, respectful compliments about her appearance (“you've made a real effort tonight and it shows”), and he's approached with a fun, casual, physical approach, which comes naturally to him. A solid flirt.

Dealing With Rejection

Romantic rejection is an inevitable part of flirting and dating, and the best flirters know how to take it on the chin. This improves their ability to flirt because they come off as relaxed and unfazed, whereas a disproportionate fear of rejection makes you come off as insecure, and sometimes causes you to behave in controlling and preemptively-defensive ways (“I bet you’re sick of hearing how pretty you are, so I’m not going to say it.”)

One good thing about the pickup-artist community is that it promotes the idea that flirting opportunities are abundant, so you don't need to be too devastated by any one particular rejection.

Unfortunately this tends to be framed in terms of markets and statistical models that make women sound more like commodities than people, but the underlying principle is an old and sound one — think of your parents’ saying, “there are plenty more fish in the sea.”

Bearing this in mind takes the pressure off any one particular encounter and helps you regain perspective when things don't go as well as you hoped.

Check Your Level of Sexual Intensity

Just because sex might be a goal for you doesn't mean that you should bring it up right away. Immediately descending into explicit sexual territory is likely to make the woman you're with feel uncomfortable, no matter how open-minded she is.

This will come across as creepy rather than smooth, so keep it above board, and at most allude to sex in a refined, low-key way once your conversation has been going very well for quite some time.

Better yet, let her take the lead on this. If she wants to make the situation sexually charged, she can, but there’s no sense in you trying to force it.

Don't be like this guy.

Consider the Conversation Topics

Conventional flirting advice recommends avoiding heavy topics such as religion and politics, which is generally sound for a first encounter, but if you want to make a lasting impression you’ll need to delve a bit deeper than safe topics like work or the weather.

These “water cooler” conversation starters run the risk of rendering you boring and forgettable, whereas bringing something more thoughtful and novel to the table will make a better impression. This is especially the case for online dating: While a confident, “Hello! How are you?” can be a decent start when delivered in the flesh, it's a pretty entry-level opening on a dating app where women are inundated with identical approaches.

This is not to suggest, though, that you should be pointlessly controversial, deliberately offensive or play devil’s advocate for the sake of it. Flirting is meant to be light, engaging and convivial, so try to hit the sweet spot between banal small talk and heavy, debate-laden topics.

A good starting point could be a respectful, genuine compliment, followed by an interesting question (“what's your favorite book/movie/song?” is better than “so what do you do?”), before moving on to explore any mutual interests.

Keep It a Two-Way Street

When you’re flirting, it’s important to ask lots of questions and to be interested in the answers. Ask follow-up questions. Most human beings want to be thought of as interesting rather than always simply being in the presence of more interesting people.

That can lead to one of the biggest potential flirting pitfalls: if you try to be too confident or showy, you might leave her feeling as though your encounter was the "you show," in which you paraded and peacocked at the expense of making her feel entertaining or interesting.

Remember that flirting should be a mutually enjoyable encounter rather than a performance, and you should see the person you’re flirting with as a whole person, not simply a target.

Flirting is an art that most people approach with some sense of insecurity and hesitation. If you only compare yourself to the Don Drapers and Joan Harrises of the world, you're going to feel as though you are uniquely bad at flirting, but you're almost certainly not.

The fundamentals are simple: treat potential dates like people, not strange aliens from Planet Woman; pay attention to body language; approach in an appropriate environment; and keep the conversation interesting, flattering and convivial.

Armed with the above tips, plus a philosophical approach to rejection and a healthy view on gender relations, you can't go too far wrong. Why not make today the day you finally approach your crush with some flirtatious banter: the worst she can say is “no,” so you've got everything to gain.

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