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 can 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.
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?”
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.
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.