For a long time, I didn’t know how to flirt at all. I knew flirting was important because it shows her that you’re romantically interested, but I just had no idea how to do it. It was embarrassing for me because I had assumed that knowing how to flirt was something that everyone was naturally able to do.

Well, everyone except me that is.

Eventually, I came up with my own way of flirting that’s authentic to my own introverted self. It’s gotten me dates and meaningful relationships naturally without making me feel sleazy or like a pickup-artist. If you’re like my past self and you have no idea what flirting is or how to do it, then I’m going to show you in detail how I personally flirt.

Just in case you were too embarrassed to ask.

The five styles of flirting

What comes to mind when people talk about flirting? Stuff such as winking, sideways glances, small touches, and double entendre.

It’s true that these types of signals can be considered flirting. However, these only describe one kind of flirting. In his book The Five Flirting Styles: Use the Science of Flirting to Attract the Love You Really Want, Dr. Jeffrey Hall identified five different types of flirting:

• Playful: Flirting for fun without any expectations that it will lead to sex or a relationship.
• Physical: Flirting through body language and sexual communication.
• Polite: Flirting through proper manners and nonsexual communication.
• Sincere: Displaying sincere interest in the other person to develop an emotional connection.
• Traditional: Displaying interest through traditional courtship rituals and behaving in ways that are “gentlemanly” or “ladylike”.

(You might look at this list and tell right off the bat which style you are. Otherwise, you can also take an online test to determine which flirting styles you are here. It’s similar to the Myers-Briggs and my results are polite + sincere.)

A lot of flirting advice is centered on the physical and playful styles of flirting. There’s a lot of readily available advice about how to approach women in bars and clubs, or what pickup lines to use, or how to get touchy-feely with someone you’ve just met. This kind of flirting style works well for people who are looking for short-term romance or just trying to have fun.

However, this method of flirting felt inauthentic to me. I’m not a fan of using the bar and club scene to find romantic connections, and I don’t like flirting that’s too crude or dirty. When it comes to sex, I’m more interested in doing it with someone that I deeply care about.

The way I flirt is a bit different.

First contact

If there’s a woman that I’m interested in talking to, the first thing I do is to try and meet her eye. I watch her out of the corner of my eye and wait for her to glance in my general direction. When she does, I turn towards her and “accidentally” make eye contact while smiling. In an ideal world, I’d always be able to pull off the eye contact + smile before I try to talk to her because it helps warm up the first approach. However, sometimes it just doesn’t happen. Maybe she’s too absorbed in what she’s doing to make eye contact. If that happens, I still try to talk to her anyway and just do the best I can.

By the way, if the two of us are at a social event such as a Meetup group or party then the eye contact + smile is not necessary. It’s socially acceptable to just go up to people you don’t know and introduce yourself at events such as these. Chances are she’s going to be glad you did! After all, it totally sucks when you go to a party or gathering and nobody tries to talk to you at all so you pull out your phone and pretend to be texting someone so that you don’t look lonely.

I’ll walk over to her and open the conversation by simply saying “Hi”. That’s it. No need to try and find the perfect line or to be flashy. Just saying “Hi” is simple and authentic. After that, I try to continue the conversation by talking about something contextual. For example, if we’re at the library then I might ask her what she’s reading. At a Meetup group, I might ask her if she comes to that group a lot. At a party, I might ask her how she knows the host.

From there, I pay attention to how she responds when I try to talk to her. If her responses are short and curt then she’s probably not interested. When that happens, I just wish her a good day and move on. However, if she tries to hold a conversation with me as well then that’s a good sign. In that case, I try to find something that she would be interested in telling me about herself. In the classic book How to Win Friends & Influence People, Dale Carnegie encourages talking in terms of the other person’s interests and listening to then with genuine interest. This is the sincere style of flirting.

As the conversation begins to wind down, I lightly touch her on the arm and see how she reacts. If she pulls away or doesn’t react at all then she’s most likely not too interested in me. When this happens, I’ll simply end the conversation with something such as “It was nice meeting you” and then move on. Now, if she responds by smiling or moving a little closer when I touch her on the arm then that’s a good sign. In that case, I’ll try to ask her out by saying something like “Hey, I’ve had a really great time talking to you. I’m planning on going to [place] at [date + time]. Would you like to come with me?”

On dates

When I first start going out with a woman, my flirting styles tend to remain polite and sincere. For me, sexuality and emotions are closely tied together and I won’t do anything sexual unless I really feel emotionally comfortable around her. Even though sex on the third date seems to be the norm in today’s world, I don’t like to get sexual until I’ve known her for at least a few months.

Instead, I simply try to get to know her better on those first several dates. What does she like to do? What are her hobbies? Her dreams? What do we have in common? I try to learn more about her as a person and I take her out on activities that have no sexual undertones, such as playing mini-golf or bowling or ice-skating.

As I get to know her better, that’s when I start feeling emotionally ready to move towards more physical and playful flirting. I’ll initiate the first kiss after around seven or eight dates and, as we move from dating to being in a relationship, that’s when I start being more freely sexual.

Finally, I try to mirror her flirting style as best I can without being inauthentic to myself. For example, even though I personally don’t initiate first kisses on first dates, if she’s the one who wants to kiss me then I’m not going to stop her. However, if she wants to have sex on the first date then I’ll turn her down. It’s inauthentic to my personality to sleep with her on the first date.

When to go for a first kiss

(If you’re really unsure about going for a first kiss, it’s perfectly OK to just ask her if you can kiss her. You can basically skip this section if you go that route.)

This was always nerve-wracking for me. The last thing I wanted was to misread her signs and go in for a kiss she doesn’t want.

The short answer to go for a first kiss is when it “feels right”. Now, what do I mean by that?

The first kiss means different things to different people. To people who prefer hookups and casual flings, the first kiss might mean little more than “we just met in a bar, and I think you look cute”. And on the other end of the spectrum some people interpret the first kiss as “we’re basically ready to get married”.

Just like every person has their own valid flirting style – EVERY interpretation of the first kiss is also completely valid. The key is to find someone you are compatible with.

That’s why I’ve historically waited six or seven dates before going for a first kiss. To me, that first kiss is heavily emotional and basically means we’re at that level of being girlfriend/boyfriend. I’m from a rather conservative background and the women I’ve dated have often shared traditional views so it just “felt right” to wait that long. You certainly don’t have to wait as long as I always did!!

So, how long does it take until the time “feels right” for a first kiss? Again — it depends — but I’ll tell you how all 5 of my first kisses happened so you can get an idea of what that might look like.

• My “first kiss ever” was in my sophomore year of University with a classmate who I had a crush on. Turns out she liked me back but I didn’t know it!! She actually invited me to her place because she “forgot” something in the classroom and asked me to bring it over to her. We ended up play-wrestling-tickling each other in her room and the next thing I knew our lips locked together and our tongues were doing the wrestling. Turns out, tickle-wrestling until you’re a sweaty mess builds a lot of sexual tension!! (Excuse me, I just got really hot and bothered writing this…)
• My next “first kiss” was with a woman from a very conservative background (which was OK with me because I was raised similarly.) She insisted that she only “dates for marriage” and didn’t even entertain the idea of a first kiss until several dates later. Our first kiss happened spontaneously at the library when she blurted out of the blue “I want to kiss you”. She admitted that she started wavering with her traditional beliefs. It was as romantic as a first kiss at the library could be (i.e. not so much) but we ended up going back to her place and having a proper make-out session for our second kiss.
• Next, I dated someone that I was introduced to by a mutual friend. In stark contrast to my dating history, she was QUITE sexually liberal and invited herself to my apartment one night after we had gone on three dates (I had never even told her my address but I’m assuming she got it from my friend). We pulled up two chairs together and watched “Jerry Maguire” on my TV. She kept glancing over at me during the movie and, at first, I was wondering if she saw a bug or something in my room. After a few times I decided to glance back at her when she did that. She held eye contact for the next several seconds. I leaned in slightly to see how she would react. She responded by leaning a bit closer. I leaned in a little bit closer. We watched the rest of the film on my bed holding each other for warmth.
• My next “first kiss” was with someone I met through online dating. She kissed me on the first date and I didn’t turn her down. It honestly didn’t feel that special though and I asked her out again but we never ended up going on a second date.
• Finally, I was introduced by another mutual friend to a woman named Mia who later became my wife. She came from a conservative background as well and would not even consider going back to my place until several months of dating (even though I offered to cook her dinner or set up a movie at my place several times). She eventually was OK with seeing my place after knowing each other for a while but I decided not to push it and still waited for a few more dates because of her background. One day we did end up play-tickle-wrestling at our place and that eventually led to our first kiss.

Ok, so how do you pull it off when you ARE ready?

Try to read her signs and gauge how comfortable she is. Does she lean in to you a lot? Is she comfortable sharing her personal space with you? Do you notice her turning her face toward you?

What if you responded by turning your face to hers? Lean in a little bit. Does she turn away? Does she lean in a little more? If she seems receptive, try leaning in a little more.

And a little more…

And a little bit more…

Until…

There’s no wrong way to flirt

This is how I personally flirt. There’s no “right” or “wrong” way to flirt, and this just happens to be the way that I do it. My flirting style is primarily polite and sincere. I’m just a little playful in that I try to smile and wink at her with a few light arm touches, but otherwise I keep it mainly nonsexual for the first few months until I start to feel emotionally comfortable around her.

Of course, you don’t have to do it this way but I wanted to present it to you and show you what my polite + sincere flirting style looks like. If your personality is similar to mine then you may be able to adopt my style for yourself. Feel free to keep the parts that you like and discard anything that doesn’t fit you.

The most important thing to keep in mind is to be your best authentic self around her. No matter what your method of flirting is, there are always going to be women who are turned off by it. Since I don’t kiss until after seven or eight dates, women who are looking for casual sex aren’t going to find my flirting style attractive. That’s totally okay because I’m not the type of person who enjoys casual sex.

Flirt in the way that’s authentic to you, and trust that the right women will find you attractive.

How do you tell the difference if she’s flirting with you or just being polite? I was always horrible at that.

My friends would sometimes tell me that “such-and-such” had a crush on me, or that another woman I was talking to actually was trying to hit on me, but I never really believed them. I thought my friends were just trying to be nice and “psyche me up”. It just seemed like the women I was talking to were simply being friendly.

Looking back I think a lot of it was just fear of rejection. I would psyche myself out of it and tell myself “she’s probably just being friendly”, “she’s probably not interested”, or “she probably already has a boyfriend” even when in hindsight it was obvious that she was flirting.

• One time, a female friend texted me at 10pm saying she was going through a rough break-up and asked me if I was free that night. I told her “No, it’s late. I’m going to bed. See you later.”
• Another female friend invited me to her apartment for board games, cooked dinner for me, and then spelled out “want sex” on a Scrabble board. My response? “Okay, that’s +19 points for you.”

And that’s why I was single for so long…

So, how do you know when someone is flirting with you? And how do you flirt back?

Continue reading The “best” way to flirt — according to science →

So, was there a class on flirting that I missed when I was younger? It seemed like everyone else already knew how to do it and get into relationships. And whenever I tried to get advice, all I heard was “learn to flirt” with no explanation.

Today I have both a long answer and short answer for you. The long answer is quite technical and scientific…but it’s also a great read so I’d recommend checking it out when you got a sec.

And for the short answer—

I’m going to do something I don’t usually do and recommend a specific flirting technique that you can use today from former-pickup-artist Mark Manson’s book Models called “cold reading”.

Now, I have A LOT of contempt for PUA and it’s not something I would typically touch with a 10-foot pole. It’s also been scientifically proven that everyone’s flirting style is also different, so recommending a specific flirting technique for everyone—especially one from the world of PUA—seems like a weird thing for me to do.

So, what gives?

I’ve previously written that dating advice which appears independently in multiple places—especially outside of the realm of dating advice—is generally worth following. Cold reading happens to fit that bill. In the book Never Split the Difference, Chris Voss describes a similar technique he calls “labeling” or “tactical empathy” that he used to negotiate with hostage-takers back when he worked for the FBI.

You might even see this sort of technique in the world of competitive gaming (yes, really) where it’s called a “hard read” or “reading your opponent”. I’ve done it myself in many online competitions.

Seem like something worth knowing? Let’s get into it!

Continue reading Don’t know how to flirt? Try doing this!! →