Flirting is the art of poking fun at someone playfully, while amplifying sexual tension. When kids do this, it is called teasing; when adults do it, it’s called flirting. Treat her like your younger sister, who is slightly quirky, and maybe in need of “extra help”. Or, misinterpret her actions as her flirting with you, misbehaving, or otherwise “up to no good”. This playful teasing is known as “flirting”. Ideally, you can blend in a bit of cockiness, which when combined with humor is an explosive combination.

One note on being cocky, don’t overdo it! How many times have I seen a guy go out to a bar or club and not notice if the woman is having fun or not! He will always ruin his chances by not paying attention, and blow the opportunity by not toning down the cockiness. This is a sign of both low social intelligence, and insecurity. Guys who are purely cocky are insecure and considered arrogant. They have to bring down someone else to make themselves feel good. Now, it is fine to be cocky, but you better mix in the humor. Your gauge should be whether or not she is having fun. Otherwise, she will think you are a jerk.

Flirting is the perfect way to maintain and continue a conversation with a woman. It is also a great way to hook her by revealing your sense of humor while creating some sexual tension. Another way to think of flirting is that you are purposely creating a negative emotion. If you combine it with humor, this slight insult will come across as flirting. For example, you might call her a “brat”. This is a negative thing to say, but if you do so with a smile, it instantly becomes flirtatious.

An essential skill required in all social situations is listening. In flirting, listening is doubly critical. She will often hand you beautiful opportunities to flirt, but you must be present enough to hear them. So, if you are stuck in your head wondering “what is the next thing I am supposed to say”, you are sunk my friend. As you develop this skill, try to listen more and think less so that you are more engaged with the real conversation.

What do you listen for? Well, certainly listen for facts and details about her life. It is very impressive if you can recall them later in the conversation. With the art of flirting, try to listen more for ways to misinterpret what she is saying. Or, if she misspeaks  you will definitely want to tease her a bit about that (Freudian slips are great opportunities to flirt). You don’t want to overdo any skill in a social interaction (flirting, baiting etc), so try to mix things up. But you always want to listen, and be present to the interaction.

mens guide to flirting

Skillful flirting reveals to her that you understand emotional communication, and that you are not going to be like the average guy who waltzes over and engages her with boring Q&A. You are different kind of guy, and know “the code” so to speak. A guy who goes in and tries to shower her with positive emotions from the beginning with compliments and questions usually is seen as needy. You want her to earn the good stuff, so you don’t give it away immediately. Once she earns, it, feel free to give it to her. Until then, set the bar high, and flirt away. Let me give you some examples of what I am talking about:

• You guys are mean. You remind me of the playground bullies in 3rd grade, who used to throw sand at me. Of course, those kids eventually got kicked out of school…problem children…jailbirds now…see what you’re in for?

• (If she is asking lots of “testy” questions) I like that you are asking so many questions, it shows that you are both curious and intelligent. You remind me of Polly Matson who used to sit front and center in 5th grade to impress the teacher with her hard questions. (then, if she continues asking questions, refer to her as “Polly”)

• (If she teases you about your clothing) How adorable, we got Joan Rivers’ second daughter here…

• (If she condescends to you in ANY way) “OK, little Lucy from Charlie Brown… we need to get you a football and a little blue dress…awfully feisty…”

• A playful disqualification can often have a very strong effect: “You know, me and you, we would just never match – we are too alike, and that just means a load of drama and heartache…” Again – say this with a smirk, a sly smile. From here, you continue to talk with her etc. Beautiful women are not used to hearing things like this at all. By the way, what are beautiful women used to hearing?:

“Let me buy you a drink”
“You are so gorgeous”
“You are so hot”
“Can I have your phone number?”

Please guys, avoid these comments! The men who say these are instantly categorized as being “needy” and “creepy”. This is obviously not the impression we are trying to create! Instead, learn to demonstrate your personality in a way that engages her, causing her to be interested in knowing more about you. This way, she chases you and not the opposite. If you can do that you will win big-time.

Are you noticing a pattern here? What you say and how you say it are completely opposed. This is where the tension is created. You might say a slight insult, but accompany that with a smile and a raised eyebrow, for example. This combination of humor and a bit of cockiness slowly increases this tension. Often, when you are flirting, you are saying things that could be interpreted as negative. This is why doing so with a sense of humor, and a smile, is so important. Guys who are good at this never hear “let’s just be friends” from women.

So, let’s break this concept of flirting down into some basic guidelines:

• Must be done playfully.

• Make fun of her – better to stay away from how she looks, what she is wearing etc as women tend to be very sensitive about these things. Although, if she is wearing something that is obviously seeking attention – feel free to bust on her for it – tease her about “needing attention”…”you are an only child aren’t you – so sad, playing your little Lite Brite all alone…”

• Cockiness is helpful – why? If you are cocky, this subtly communicates that you don’t care, even though you are there to talk to her. This keeps her off-balance and guessing. But don’t overdo it!

• Listen – I can not emphasize this enough. Women will often give you gold in the conversation, but you must recognize it. Also, if you are really listening, you
might notice that she is subtly flirting with you. This is obviously a skill that
is a must across the board, but it is so vitally necessary when flirting. How else
are you going to know when to STOP flirting and transition into the “connect”
phase? Listening is a critical social skill.

• Ultimately, try to mix in some complimentster), otherwise you will never stop flirting. By complimenting what you observe about her, it proves that you are paying attention, that you have very good conversational skills, and that you understand how to lead and direct a conversation. If you want to see her again, you need to instill some comfort. Complimenting her is a great way to begin establishing a connection, and to encourage her to reveal a more real side of herself to you.

One important note before I leave this topic (and I know I am repeating myself). There will be times when cockiness will be inappropriate. I mention this because guys love to use cockiness when speaking with women. If it is overused, it can destroy your chances of having a real conversation with her. Also, if you can sense that the woman is already attracted to you then it is wise to flirt and tease only very lightly, and then transition into a more normal conversation. Less is more here, and if you do get overly cocky with her, she is likely to think you are a jerk. So, do everything you can to avoid this pitfall!