Flirting Tips for Men

By Matthew | May 4, 2020

Dear Kendra,

I love to flirt, and women seem to enjoy flirting back. The casual fun flirting is a blast, and I enjoy it. But I never know if they want to move from fun flirting to something more serious.

I’ve tried a few times to make the change to serious flirting, and found out I was wrong, and screwed up friendships. So for the past few years, I just automatically default to “it’s just for fun” and don’t even try to “make a move.”

So I guess what I’m asking is – is there any good indication that a woman is interested in moving the flirting from “just for fun” to something with more intent? What Are Best Practices for Men Flirting With Women?

My reply:

I’m going to turn this one over to Matthew! Now, this is a man who is not into tricking or manipulating other people.

He takes “master pickup artists” and picks them up and tosses them in the dumpster.

He practices open and honest communication.

He doesn’t have a GQ model body, but he has the confidence of Zeus.

He realizes that not every woman wants to be with him, and HE’S OK WITH THAT. He’s only interested in being with women who are genuinely into him. Somehow, he manages to play the situation so that he KNOWS the woman is desperate to get to his cock. At least, that’s how he played me. For months. The bastard! Sigh, I’m hooked.

Take it away, Matthew….

Matthew says:

This is a great question and I am going to address it on a number of levels. Specifically to your question, first and foremost what comes to mind is an encounter I had with a woman some time ago.

Now, I know that everyone is different and situations even more so, but I believe it demonstrates something that could be of benefit to you. This was a first date, spur of the moment situation. I knew her previously but only casually. At the end of the evening we had sex. It was after these cues that I knew I was going to have some sort of sexual encounter with her:

1. She texted me, asking me to join her for drinks.

2. She was watching for me when I walked in.

3. As the night went on, her communication and body language became more focused on me rather than the environment.

4. She started touching me. In this particular case, it was her hand on my thigh, my shoulder or the back of my hand as it was sitting on the bar.

5. She never once indicated that she needed to leave or was not mentally present.

Those points being said, there were a number of things prior to that evening that were positive. Perhaps the biggest was that she would text me unprovoked, which meant it didn’t take a signal from me for her to think about me.

In thinking about your question a bit more in depth and hearing of similar interest from others, I have come up with some Stages of Flirting.

Romeo was looking up, offering his heart to Juliet through a….

Window- General information about yourself and every day life. Letting someone know you are interested in them and attracted to them. Divulging your relationship status in a concrete fashion. Windows let fresh air into your life. They can be open for long periods of time AND at varying intervals. This is where the majority of information should be attained and accessed. Then you can decide whether or not to knock on the….

Door- This is the stage at which you let someone know what you are looking for and what you like sexually. The first physical contact happens most often in this stage. Once the door is open, you must either go through it or close it. Don’t spend too much time standing on the threshold. You want to get your feet on the…

Floor- Foreplay flirting happens here. Planning sexual encounters in detail. You are definitely in at this point, if not already having sex. This stage also includes continued flirting to lead to more encounters together. Just think of all the things you can do on a floor.

The Window stage is the most important as far as I am concerned. I like to let this one last for a while, and by that I mean three weeks at a minimum. When people know you aren’t desperate, they become more comfortable and more attracted to you as they go experience negative energy and drama elsewhere.

**Note: If you are desperate, you need to fix that. Take a deep breath and commit to the courting process. Nothing will come to you without a bit of work. Having a sexual partner is not a right to which you are entitled by age, race, color, creed or cock size; rather, a privilege and an honor that you are rewarded with after proving yourself worthy.

Here are a few other concepts that I think men(and people for that matter) could benefit from offering more attention to:

Chivalry is not dead. In fact, we need to demonstrate it more than ever. Keep in mind that chivalry is not only being honorable toward women, but to everyone regardless of classification(s). Open doors for people. Be polite and respectful. Be generous. Be as honest as possible. Be protective of, and loyal to those close to you. All the while, demanding a certain reciprocation of those values you put forth. If you do this, people (women included) will notice and you will be compensated in many ways, with varying types of currency.

Don’t let technology get the better of your communication with others. It is imperative that you interact with people in person, face to face, eye to eye, smell to smell, taste to taste and touch to touch. If you use all five of your senses, you will have a much better idea of whom the person is you are communicating with. I think there are a lot of people that meet via the internet, communicate via the internet and text so much, that they actually develop a relationship contingent upon a lack of intimacy. Then, when they meet face to face, the dynamic is negatively different.

I also think people use alcohol in the same way they use technology, as a filter and a buffer. We all know that alcohol creates a certain type of courage not normally enjoyed by the user. Much like technology, if alcohol is too much a part of the communication equation, it can lead to really negative situations.

Finally, bring something to the table. Anything. Know what you are good at and passionate about. Highlight that if you can. Be clean and on time. Choose potential partners not necessarily by sight, but by observation if you can. Take an interest in what they do, but only if you mean it.

Love something in your life and something in your life will love you back.

TBK Community: What works for you as far as flirting and courtship goes? What hasn’t worked? When is the right time to put the blinker on and turn the corner?


IfUspamIwillHack 2011-06-16 19:39:10

This, like so many other pieces of advice, was written by someone who is already “in” and doesn’t understand that not everyone else is already in. If we were doing as well as you are, we wouldn’t be asking for advice, yet your advice assumes we are, and if we’re not then it’s not useful advice.
Kendra, please put some input in here too…I have a cock, I don’t need advice from some other dick about ladies!


    Matthew 2011-06-26 11:01:19

    I saw your comment and re-read the post. I understand the point of your comment and your point of view. I realize that I am a fortunate man who has always been extroverted as well. I think it is this reason why Kendra asked me to answer this question. I also think I addressed the question well. There are, of course, many other aspects that could be covered on the subject of flirting, dating, courting and meeting people.

    It seems to me the only anecdote about being “in” is the story I chose to open with. I think the points after that are valid for introverted and extroverted men alike. I am happy to discuss this further. This would be a good forum topic, actually.

    Please do not read this comment with a negative or condescending voice, as that is not the voice in which it was written.

    I hope we get a chance to interact more.


Creideiki 2011-07-18 14:01:39

Matt, I’ll have to shake hands with you next time we meet. What you wrote here, and elsewhere, has been a huge help to me in a budding relationship that is just getting started. I was actually able to recognize flirting for what it was in our date last night–yes, I was that much of a dolt with women once upon a time–and it’s really given me hope that she and I will go forward, and that I’ll (mostly) know what I’m doing along the way. So, THANK YOU. I will keep you and Kendra posted as time goes on.


    Matthew 2011-07-18 17:36:53

    Creideiki- Excellent!! I am so glad my thoughts and words could help. This is what I hoped for when I wrote the post. Looking forward to that hand shake and please do keep us posted!!


Adi 2011-08-11 04:21:17

I think, what there is to take from this, is that men aren’t so much the initiators as often believed. Sure, we have to make the move but it is often the women who first indicate that such a move is desired.

Try to remember also that women are also only people and don’t always know how to send the right signals.

Nonetheless, pickup artistry definitely works – unfortunately.


    Jem 2013-07-17 09:28:51

    If a ‘pick up artist’ is confident and interesting … but it’s the confidence that’s working. If I know someone’s interested and trying to impress me, I’ll give him a chance. It’s not that difficult to work out if he’s just playing some tape of chat up lines. Women aren’t completely stupid about these things. We do have moments of weakness, of course. I’ve let guys keep trying their lines … only one ever got a reward from me for his efforts, and it was a pretty mild reward.


The Nerd 2011-08-31 21:48:47

“Having a sexual partner is not a right to which you are entitled by age, race, color, creed or cock size; rather, a privilege and an honor that you are rewarded with after proving yourself worthy.” Someone who knows this, and shows this… now that is sexy!


Stephen 2013-07-16 06:07:45

Excellently written and well thought out, Beast (I still like that namesake).

I agree somewhat with the first comment, but for the reason you sussed out – confidence wins all, and it’s also crucial to show “it just doesn’t matter” if you win or lose.

In my case, I’m saddled with less-than-attractiveness and mental health issues/baggage that make me absolutely impulsive, honest, and therefore sometimes ridiculously awkward. There’s no worse feeling than making a move and subsequently having that woman avoid you like the plague. No matter how much I tell myself “Oh, she’s just immature, avoiding me and where I go rather than just being open and honest,” it comes off as “I suck. I absolutely suck. Women actually go out of their way to avoid me!”

Flirting for me is like talking, I love doing it, and I fall into the same trap – never knowing when to move on returned signals, confusing mixed signals (oh, she was touching me because she thought I was gay), so that I just flirt with everyone and wait for someone to completely and obviously return my affections. That’s the girl I’ll go for, whether we’re right together or not.

I make these statements just to point out there’s a lot of “me’s” out there, and to bring community to the first commentor and the original questioner. I know full well that folks like me need more than just one well-writ answer to cure the ails…hell, I’m still like this after 7 years of therapy.

But for those who just needed a little jolt, some keen advice, and a boost, your answer did it – and Kendra’s reception to you clinched it – confidence, a lack of desperation, and respect for the woman (which includes NOT pursuing too many women at once).



Stephen 2013-07-16 06:10:57

And here’s a question *I* have for Beast to answer:

Matthew, when you’re in a Dom/Sub situation with Kendra, she has described going through intense emotions. Based on her descriptions, while you are a ‘beast’ with her, you are always respectful and check in with her.

Here’s the Q: Have you ever “lost it” during a session? Gave in to your own intense emotions? Started beating too hard, went a little nutso during or after? How do YOU handle the intense emotional possibilities of rage/anger or allowing your own inside junk to pour out of you into your strikes and spanks?


Jem 2013-07-16 09:44:26

As a woman around Kendra’s age, for me, it’s all about confidence and attention. For me, it’s a bit like … moving to a new place or buying a car. You just know.

My tip … be confident, be the best version of you. Don’t try ‘moves’ or ‘lines’ or to trick us into bed. Just be comfortable. Understand that women are just people, that we may be tired or have had a bad day. Smile and talk to us. Look … we’re probably just as insecure and weirded out by being in that bar, or wherever we are.

Communicate. Be truthful. Listen. Listen.

As for Matthew’s three week courtship thing … well, it depends what I’m looking for. I’ve had relationships where six months of friendship has turned into something more. And I’ve been to a party where I made eye contact with a guy, and – a little to my surprise – the first thing I asked was whether he had a condom.

Best advice I ever got: try to be someone *you’d* want to date. Don’t try to unlock the secret opposite sex code, just … be someone interesting, honest and thoughtful.


Sandy 2013-07-18 12:15:06

You never know if a woman wants to move from fun flirting to something more serious? Well, sometimes they don’t know either. You have to enjoy flirting not knowing. Likewise, don’t forget to flirt even when you both know it’s going to lead to sex. And also enjoy flirting even when you both know it’s not going to lead to sex. It’s all about complimenting and having fun.

You flirted to such an extent that you screwed up friendships?? You weren’t listening to the reactions to your flirts! It stops being flirtation if it feels like pressure. The flirtee needs to feel there is a choice with good consequences either way.

It’s impossible to give anybody a sure-fire line that will work as a flirt because it depends so much on individual humor and context. One of the no-pressure no-assumption flirtations I’ve used are corny turn-the-tables lines like “So when we go on the hike, we’re going to be alone, and I just want to know you’re not going to try to take advantage of me!” said with a sheepish grin. Her reaction will tell you a lot and your next flirtation will entirely depend on what that reaction is. One response I’ve gotten was just as teasingly ambiguous: “I don’t know, I’ll try to control myself!” That would be a pretty positive response, but without any commitment on her part. And so the flirtatious give-and-take continues… It’s all about LISTENING to her reactions as part of the comedy and having fun. When flirtation is really fun, it feels to me like I’m in a funny sitcom, like a scene from Friends, where you’re on the edge of laughter all the time.

And there’s something about that phrase in the original question that bothers me, “move from fun flirting to something more serious”. More serious? That word alone turns me off, as if the fun suddenly had to come to a stop.


Hector 2019-11-21 17:50:23

I have confessed my love to many women, who were classmates of mine when I was still a student or even women I had never talked to before. One time, I even knocked on the door of a celebrity (not worldwide celebrity; she was famous in my country only) and told her I loved her. I would be turned down every time. Since I have never had any friends, I did not run the risk of ruining friendships, though I think that, if a friendship is ruined because of that, it’s all in your (and the woman’s) heads.

Anyway, all the above was a long time ago, when I still pursued ‘happily ever after’. Nowadays, I no longer know what I want from women. I reveal stuff about me and my past experiences little by little on my blog. If you’re interested, the links to my blog (new posts every Sunday), as well as to my author page on Amazon (where you’ll find all my novels), are below. Follow me and advertise me to your friends and on social media.


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