Flirting Guide


The Gentlemen’s Ultimate Guide to Flirting

Communication – all kinds of it – is the backbone of human relations. Our sophisticated means of interacting as a species is what differs us from other animals; what helped us build entire civilizations; what allows us to express our emotions and opinions, bonding beyond instinct.

Flirting - Communication is Key

And yet, it is fair to say that despite millennia of practice we are still far from mastering the art of communicating. Perhaps because we tend to see it as a one-way road, an individual act as opposed to a reciprocation.

Or perhaps because we overlook the impact of culture in our language –  either verbal, symbols, gestures or any other form of expression – and how social stereotypes affect the way relate to each other. Whatever the reasons may be, communication touches all spheres of life and when it comes to interacting with people of the opposite sex it is no different.

All men have, at some point, considered how to ask a girl out, and when that happens our flirting abilities (or lack thereof) spring to mind. In essence, to flirt is to establish that first bond with a girl, be it through conversation or a look. But to truly learn how to flirt with women, one must first look beyond the action, to the underlying factors that may make or break communication.

Flirting - Not Good at Flirting

Think Before You Act

There are a few points to keep in mind even before making a move on a woman; things one should always remind himself about as a means of preparing the ground before the battle, so to speak. This will make the first contact smoother both for you and the girl and, consequently, optimize your chances of actually standing a chance.


Observation is a fundamental part to create a connection with any human being you don’t know. And when it comes to flirting, establishing a solid connection is something that not only will make the first contact easier but the entire experience more natural.

In order to get to know the woman and have a good conversation, we have to leave aside our own wants and wishes and focus on her. What does she appear to be like? Does she look open and available or closed and very shy? Does she look like she is in a good or bad mood? Is she eating or maybe has her earphones on and doesn’t want to be disturbed?

Regardless of the situation, it is always good to observe a little and try to perceive the overall context the other person is in prior to making a move. If anything, it will reassure you whether or not you want to make a move in that particular situation and what is the best way to do so.

Flirting - Observe

Polish your repertoire

A lot of the one-liners that men tend to use are not only lame and unoriginal but offensive – thus ineffective. Another preparation step is to be very skeptical about what you have heard to be a good pick up line and come up with your own material. Refrain from complimenting her appearance or assume she is alone and thus easy prey. It may be worth spending some time brainstorming something that you would actually say.

Moreover, consider each particular situation for what it is, using the moment and the given person as “inspiration” for what you are going to say, always steering away from cheesiness. Sometimes a simple and polite “Hello. How are you?” can be enough of a lead to start a conversation.

Women are constantly under attack

Due to intense and frequent bad or disrespectful approaches, the majority of women have an automatic defense stance and are already expecting tenuous and/or taunting comments. Therefore, it is important to take this (unfortunate) cultural trait years of history have scarred into most societies and be extra careful on the first contact, not taking their reaction personally.

Flirting - Be Careful

Fundamental Principles of Flirting

After considering the minutiae behind the first contact with a woman, it is time to think about the actual contact. As with anything in life, practice in flirting leads to perfection – or at least better odds. Still, if you are just stepping into adulthood or trying to stir up your dating life, a handful of flirting tips can help you get started in the right direction.

Know the woman you want to address.

If the situation allows, try to avoid super-direct approaches and find out as many things about her as possible in order to help you direct the course of the conversation. Ask her about a good movie to watch or her favorite thing to do on weekends. This kind of information will allow you to unveil her profile and preferences and make the entire experience more pleasant and natural for both parties.

Call her by her name

Flirting - Call Name

Calling the woman by her name creates an intimate and friendly atmosphere as if you have known her for a long time. Just be careful not to repeat her name hundreds of times – that would create a strange atmosphere instead.

Be interested in order to be interesting

Be interested in the girl you are flirting with: Ask how her day was, demonstrate that you are present and listening and keen to know more about what she thinks and likes. As a reflex, she will eventually grow curious and start asking you questions.

Flirting - Be Interested Meme

Avoid overly busy spots

Again, if the situation allows, avoid meeting a girl in places with a lot of people. Choose a quieter location that you know well, so you can feel more confident and relaxed for being in a familiar environment and thus transmit this tranquility to her.

Do not place her on a pedestal

No matter how much you are interested in a woman, you should never think and act as if this was a unique opportunity. Not only does this behavior tend to generate anxiety within yourself, but treating her as a goddess can often work against you. Women like to be appreciated but too much praise can take away some of the challenge and mystery from the process of getting to know each other.


This could pretty much be taken for granted and yet is something many men struggle with, particularly those who are shy. Complimenting a girl is always a good move and a great way to break the ice. But when doing so choose to make deeper and more heartfelt compliments (such as a particular physical or behavioral trait) as opposed to generic one-liners.

Flirting - Compliment Meme

Opt for informal chats

Do not kick-start a conversation by talking about serious or controversial issues such as sexuality, religion or politics. Instead, go for soft conversations that cover topics like movies, books, music, parties, adventures, and even childhood memories – something to truly get to know her, not her opinions.


Be well-informed about the world in general, so you will always have something to talk to about. This does not only make you appear more intelligent but also helps to escape awkward moments.

It also helps to be active and have some hobbies.

Flirting - Open Windows Meme

Let her talk

This goes hand-in-hand with showing that you are interested. More than talking about yourself, let her talk about herself. This will both teach you more about her and make her more comfortable within the conversation. A good way of doing so is to ask her follow-up questions to an anecdote she has just told you. Alternatively, when telling her your own point of view on something, invite her to share her opinion too.

Have fun

In the end, people meet each other to have a good time and learn new things. Hence, remind yourself to act naturally, have fun and show her how much fun she can have with you. After all, boredom is not attractive.

Flirting - Vitamin U Meme

How You Act Depends on Where You Are

Public Spaces

When it comes to flirting in public spaces, scanning and familiarizing with the environment is of the essence. Is it a busy or quiet street? If it is nighttime, is the place well-lit? Is it a place where social interactions commonly happen or is it just a passageway? Asking yourself questions like the above will (a) confirm if the place is suitable for flirting and (b) show you the best way to flirt.

It is also important to notice the girl’s relation to the environment: whether she looks like she is in a hurry, waiting for someone, too distracted or too focused, with earphones on, etc. By paying attention to what she is [supposedly] doing there you can suss if she is open to dialogue and, ultimately, if you stand a decent chance of receiving a positive answer when approaching her.

Flirting - Look at Me Meme

Last but not least, be aware of your own position in that space and stay tuned for any signs she might have sent you. She might have noticed you and changed her posture, given you a longer-than-usual look, which, depending on the situation, can mean openness. Alternatively, she may have noticed you (and the fact that you are looking) and “closed up” somehow as a means to say she doesn’t want to be disturbed.

Often, either things happen too fast or these signs are utterly subtle – so it is up to you to be switched on and exercise you feel for the situation. Chances are, though, that if she has put on her earphones or opened a book she wants to be left alone; whereas if she has made visual contact, opened a smile and turned to face you there is a sign of openness.

Flirting - Public Spaces Meme

Should you feel that there is the opportunity for an approach at a public space, try to be vulnerable. When it comes to relationships, being vulnerable transmits trust which in turn increases the chances of a faster and deeper connection and approximation. Try to be open and honest about what you feel: if you are shy, tell her so.


Although nightclubs are usually synonyms to hook-ups, it may not always be the easiest spot to flirt. We are often stuck to the social norm of men-hunter and women-prey and tend to overlook our own personal style and strategies.

Moreover, the very exhilaration and vibe of a nightclub which makes us more audacious can work against us for less fear of acting raises the possibility of careless acting.

Flirting - At the Nightclub

Again, that is when the art of observation comes in: check whether the girl is alone or with friends; if she looks more into dancing than flirting. Each situation will call for a different plan of action, but in general, girls who are more open to flirting tend to look around more as if searching for something, using their eyes to approve or disapprove the first contact.

A couple of tips for flirting in nightclubs:

  • In general, all women like compliments; however, some can be more effective than others. Instead of simply saying that she is beautiful, try to identify what makes you think so and focus your compliment on that particular trait. It can be as superficial as the way she dresses or as subtle as the way she moves her hair. Not only will you bring her confidence up with the positive remark but also show that you are indeed paying attention.
  • Talking about the particular environment where you are at (do NOT read “Do you come here often?”) makes it a good icebreaker.
  • Do not assume that she is available just because she is at a nightclub. There is a chance she is really just there to dance or that her friends dragged her down for someone’s birthday party. Start with a comment and see how the conversation opens up.


Although the work space can be a touchy environment when it comes to flirting and dating – either due to company policy or conflict of interests – it is nearly impossible to stop relations from emerging. Hence, when considering how to be flirty at work be extra careful and respectful, after all, both your and her jobs can be on the line.

Flirting - At Work Meme

The corporate world is still a rather masculine environment, with many more men occupying positions of power, making this particular space even more delicate for women. Socially speaking, women suffer more judgments when it comes to their intimate life and this can determine their future within the company. With that in mind, evaluate the chances of a careless attitude reverberating negatively in her professional life.

Still, if you can’t get this girl out of your mind, here are a few things to keep in mind before making a move:

  • Move slower than usual. Different than a bar or a nightclub, the workspace is not the ideal environment for pick-up lines. Be more cautious when approaching her and only make a more tangible move when you deem the chances of a “yes” have surpassed 50%.
  • Get close to the people she is close with. Women are more likely to share their feelings with friends, which means that if she likes you there is a high chance she has mentioned it to someone close to her.
  • Try to understand her personal and professional context and base your move around that. This can be done by getting to know her indirectly, finding out anything from “Does she have children?” to “What is her role in the company related to yours?”

Virtual World

How to ask a girl out over text is yet another tricky one. We are constantly connected so it would be strange if we did not use the internet as a tool for flirting, especially for the shy ones.

Flirting - Virtual World Dating

However, gone are the days when the internet was no man’s land: We build a lot of things on the web, among them our reputation. This makes us more careful about what we’re talking about, about the way we talk and who we talk to.

So, when it comes to text flirting we shouldn’t be careless or disrespectful just because we are behind the screen. Ideally, you should always do and say things that we would do and say face to face. Sure, it is usually easier to invite someone out via Facebook than to chat a girl up in person. Even so, remember that at some point you will still have to meet and talk and when this happens she will expect you to be the same person she met on the internet.

If you are wondering how to ask a girl out online, keep the following in mind:

  • We are all doing a thousand and one things on the web; we are bombarded with an insane amount of videos, messages, work emails, news, etc. all at the same time. Therefore, you have to be witty when talking to girls on the web – perhaps even more than when in person.
  • Begin with a light, entertaining subject. Refrain from discussing overly personal or work-related topics which can either feel too pushy or too boring. One idea is to start slowly and deepen gradually – if there is openness and interest from her part.
  • Ask more than talk. We all love people who show genuine curiosity about our lives, about the lives of the people around. This extends beyond flirting online, though.
  • Leave space between conversations. Someone who gives a good morning, good afternoon, and good evening runs the risk of being interpreted as needy, so take it easy.
  • Do not insist on a conversation when the person is responding in a monosyllabic manner or when constantly viewing and not responding for a while. These may be signs that she is not interested.

However, sometimes it might be also nice to leave the virtual realm and be nice in the real world. Send her flowers, write her an handwritten letter (Your handwriting sucks? Then check out for some cool inspiration) or do something else.

Flirting - Virtual World Dating Meme 2

Be Yourself

Just like all of us, men and women, are looking for new ways of understanding and being understood, we are also looking for someone. Since flirting is often the way in which we begin romantic interactions that can lead to this finding, it makes sense that we deal with it as consciously as possible.

Honesty is key: Women can pick up when you are not being yourself. Although acting may get you a one night stand here and there, it will probably not bring you closer to finding the fulfilling relationship which all of us – regardless of how much of a “player” you are or how little you say you want to marry – are looking for.