The previous essays in this series described social confidence, how most social norms are tests, not rules, and the importance of connecting with people by helping them feel worthy of respect, comfort, devotion, and attraction. This essay discusses the six kinds of flirting.
My essays about appropriate masculinity are written primarily for my sons. So I acknowledge that being able to understand and draw up appropriate masculinity can be beneficial to both men and women, but may use male pronouns inclusively when refering to someone trying to be masculine.
Truth is a great flirt.
- Franz Liszt
What is flirting? The word means different things to different people.
Let us consider six alternatives. They are quite distinct when used individually. But people can and do combine these types of flirting. Feel free to experiment, my sons.
Remember the instruction in Matthew 10:28 to value God's opinion of you instead of people's opinion. You will have a natural and harmless desire to know whether or not your are attractive. As men, it is fun to learn how our "mirror" works. But the goal is only to know you can honestly include "I know how to flirt" and "I am attractive" in your established self-image, for the sake of building social confidence. Then you can stop thinking about flirting, and allow it to be something you do naturally while focusing on what are the truly important parts of life.
People who label themselves "flirts" will usually say that their flirting innocently asks the other person to flirt back.
My sons, I am sorry to disappoint you but I have no advice about this pastime. I am not this kind of flirt. My innuendo is dreadful. My ability to purposefully misinterpret innocent remarks as sexual is minimal. And, unfortunately, your mother is even worse at it so I do not get any practice.
Everyone understands that there are levels of increasing physical intimacy below what is sexual. Here is a sample list: hugging, ticking, playing with her hair, holding hands, touching her tushy, kissing her cheek, napping together, and kissing her mouth.
The polite way to use flirting to request greater physical intimacy is to mention the new level of physical intimacy as a verbal "ice breaker" before confidently attempting that type of touch. People do this all the time with the lowest levels of physical intimacy. "You look like you need a hug." "I bet you are ticklish!" The same procedure still works for the higher levels of physical intimacy. The only change is that people are usually more vague in order to appear less pushy. Someone might say "You have great hair" while slowly reaching for it, never saying aloud the intention of hair touching and letting the other person's body language silently say whether or not the touch is welcome. Or someone could say "Let's go somewhere else" and silently hold out a hand for the other person to hold.
My sons, remember the Rule of Sixes. In a romantic relationship you should be able to communicate six different things with one level of physical intimacy before moving on to the next. For example, you and your girl should together invent what six different hugs mean, to have a kind of secret languge together. When that is done then you can move on to six kinds of tickling. Using the Rule of Sixes keeps your romances romantic. Otherwise you progress too quickly up the levels of physical intimacy and get so caught up with where you now are that you forget about what wonders the lower levels still offer.
People who dislike "flirts" will usually say that flirting is a request for sexual intimacy. These people usually differentiate "flirting" and "trying to pick up" only in that the flirt agreeably departs if rejected. That reaction is a crude oversimplification. This kind of flirting may request any of many levels of physical intimacy, most far below the components of sexual activity.
Obviously, my sons, flirting to request sex outside of marriage is incompatible with our family's faith and morals. If you marry it will be fun to flirt with your wife in that way.
In some social situations it is appropriate to lightheartedly pretend to try to pick up a woman. Be sufficiently over-the-top to make clear you are being silly instead of serious. Be clear it is playful humor.
Why might you need to do this? It might simply show you are quirky or Bohemian. It might let a woman know that her appearance or status does not intimidate you. It can challenge a woman to qualify herself to you by her snappy reply. It might be said as if it explained your daydreaming. Or it could just be a silly part of a farewell for no reason at all.
The goal is to use lighthearted satire to make the social situation more entertaining. Communicate that you are playful and confident so you are judged as entertaining instead of creepy. You body language is much more important that which words you say.
With those caveats, I now share what are, in my humble opinion, the five most fun pick-up lines in the world.
I should note that these are certainly not the most effective pick-up lines. You can read about that experiment in Surely You're Joking, Mr. Feynman!.
Have you noticed that the only people who ask "Can men and women just be friends?" are women? Men know the answer. Men are not even "just friends" with other men. Similarly to how pre-Homeric Greek did not have a word for friend—only ally meaning someone who works with me to accomplish my goals—men bond over projects and then go their separate ways until another project brings them together again.
In other words, men must use alternative, learned social skills to spend time with people with whom they have no common interests or project. When our natural way of bonding is not available, we need something else.
Towards most women, that "something else" can be interacting with them in ways that highlight that you are masculine and they are feminine. This is another kind of flirting. It is not requesting anything. Nor does it using lighthearted satire to be entertaining. It is simply a way to fill the time and learn about a woman until you find a better common interest, or even better a common project.
The older a woman is the more she will probably appreciate this technique. Once a person accumulates societal roles (employee, boss, spouse, parent, hobbyist, club leader, committee chairperson, etc.) he or she is very rarely treated as simply a man or woman. Most men do not mind: those roles are the man's projects and he most naturally wants to relate to others within those identities. But most women miss "just being themselves" and perhaps even feel sad that they are losing track of "who they really are inside". Treating them as only someone feminine is a desired and refreshing change for everyone else relating to them by their societal roles.
This kind of flirting is easy to do. There are two steps. Suppress your inclinations to make small talk about her roles. Do not ask about her hobbies, career, or family. Instead, simply say whatever thoughts about her femininity pop into your head.
My sons, at first this may be difficult, because society teaches boys the lie that those statements are rude when said to a stranger. But a little practice will convince you otherwise. Most women you meet will respond much better to observations such as "You smell like a friend I used to know" or questions such as "How long did it take you to braid your hair that way?" instead of role-specific questions such as "So, how old are your kids?" (Obviously, be polite and do not say anything insulting. The strange woman's femininity is probably part of what prompted you to talk with her, so there will be something positive to say.)
Remember, my sons, that a key aspect of becoming charming is internalizing that most social norms are tests disguised as rules. They are only there to test your playful confidence. You pass the test by ignoring the norm. You really are allowed to—you are even supposed to—use playful confidence to "break the rule". Maintain eye contact, wear a playful smirk more than a smile, say the thoughts that pop into your head, touch people, flirt with strangers, prompt people to qualify themselves to you, say no when you are too busy to do someone a favor, do not care what people think about you, walk away from disrespectful behavior, and so forth.
A fifth kind of flirting simply lets a person know they are attractive.
Men and women want to be attractive in different ways, so they do this kind of flirting differently.
This type of flirting works best with people you have just met. It is a form of public service. Making strangers feel attractive increases the local happiness level. And never seeing the person again protects you from possible misunderstandings that you are more hooked or smitten by them than you intended to express.
Most women feel attractive when two conditions are met. The writers of romance novels, who know their heroines must be exemplary in what makes women feel attractive, are quite aware of these conditions. That genre uses the nicknames twu wuv and the magic hoo hoo. The first describes how a woman can "hook" the man she wants because her personality is unique and special. The man, no matter how many women he has felt love towards before, is overwhelmed by what she alone offers him with her wonderful and distinctive company, and is so enchanted he becomes permanently hers and desires no other woman's companionship. The second describes how her sexuality is unique and special. The man she wants, no matter how many women he has been sexual with before, is overwhelmed by the singular physical and emotional chemistry he has with her body, and is so enchanted he becomes permanently hers and desires no other woman's sexuality.
Note that most romance novel heroines are "unawakend women" who are unaware of the charms of their personality and sexuality: it is important that the twu wuv and the magic hoo hoo hook her chosen man in the story without her planning or effort. (Women want to be desired for who they are, not what they do. If she has to do something then she feels unattractive.)
Therefore, an attractive man can help a woman's self-image by giving her a genuine, unsolicited, unexpected, and innocent compliment that shares a specific detail of how her unique personality or sexuality is captivating. Be sure to emphasize that no other woman offers that virtue. "I have never met a woman with whom I can so easily to talk about hiking" may not sound like anything special to the male brain, but it will probably be the highlight of her day. Or perhaps "Sorry, can you repeat that? When you smiled your dimples were distracting." To you, my sons, as men, that probably sounds disgustingly needy and lecherous. But I assure you that for many women reading this essay that was their favorite part.
Men, unsurprisingly, want the opposite of what women want. Most women want the ability to uniquely and permanently enchant a single chosen man. Most men want to be able to enchant every woman they meet in a common and temporary way.
This also has two parts. The first I will nickname enjoying his zone. The man wants any woman he meets to immediately and instinctively recognize that his playful confidence makes a zone around him of safety, comfort, and relaxing fun. When he approaches near enough so that she enters his zone it makes her smile. If he takes a step back, she steps forward.
Note that men realize, without envy, that all attractive men generate this kind of zone. Men do not need to feel attractive in a unique or special way. They instead want to be attractive in a normal way to as many women as possible. They realize that some women will be unresponsive to any man: they are having a bad day or have a sour disposition. This results in a numbers game. No man will have every woman respond visibly to his zone, but what percentage does he get? The higher the number the more attractive he feels.
The second part I will nickname morphing into his projects. Men recognize that when women who are around a very attractive man will change, like harmonious chameleons, to adopt his hobbies and enjoyments. This change is without guile. Part of what makes a man's personalty attractive is how he pursues his projects with initiative and skill. A woman who opens herself to receive that man's masculinity will genuinely find those projects entertaining. Thus a men feels attractive when a woman is open to joining in his hobbies and diversions, even if only momentarily. Once again, men realize that this dynamic does not make them unique or special—instead they notice what percentage of women they affect.
This second male dynamic is somewhat equivalent to a woman's twu wuv. His company allows his masculine energy and her feminine style to blend so they enjoy life better together. His personality is so strong that its proximity causes hers to merge. But wise men know a woman's morphing is temporary. If the woman spends time away from the man her new interest and enjoyment in those activities will vanish. If the couple continues to spend time together but he ceases to pursue his projects with his earlier intensity and skill then she also changes back. ("We've grown apart," complains the discontent wife who successfully tamed her husband's project zealotry.)
To help a man's self-image, a woman thus merely need to smile when he approaches, maintain a comfortable but constant distance apart while talking, and once ask him to demonstrate an aspect of his projects. To a woman's mind saying "You swing dance? Show me" seems awkwardly needy and forced. But her saying "show me" about something will will probably be the highlight of his day.
Another way women's and men's ways to feel attractive are opposite is that men do not mind putting forth a bit of effort to be desirable. This is why men sometimes tell a woman to feel safe or relaxed, or offer to show her some aspect of a personal project. He is using the woman's visible response, or lack thereof, to check whether he is attractive. Doing this is the male equivalent of women looking in mirror before leaving the house. (My sons, our male "mirror" is more honest!)
Finally, note that the best way for both men and women to increase their attractiveness is to develop more playful confidence, for it makes people more unique as well as strengthening their presence.
The last kind of flirting simply tests if a person feels you are attractive. This is obviously different for men and women because of how men and women want to be attractive in different ways.
For women, this is easy. Simply ask a man for a unique and special way he enjoys your company. If he has a quick and genuine answer, then your hooks are working.
For men, any tests work that check whether she finds your zone is refreshing and if she is allowing her style to merge with your energy. But the best pair of tests are, unsurprisingly, old-fashioned classics. Now they are quaint, but still work well.
To check whether she will allowing her style to merge with your energy, simply offer her your elbow as if you wanted to walk away arm in arm. If she accepts, she is willing to follow your lead. (As before, if she is not then find someone else to spend time with instead of trying to "make it work". It won't work.) You do not need to actually go anywhere. You can always look at her, give her a big smile to thank her for being agreeable, release your arms, and say something like "That was adorable" or "You pass the test".
To check whether she feels and appreciates your zone, kiss the back of her hand while you watch her eyes. Do not move too quickly or slowly. You are not trying to surprise her or be sappy. Bring her hand up as high as is comfortable for her, so you do not bend forward any more than necessary. Maintain eye contact. As soon as she breaks eye contact, stop the kiss and gently return her hand down a bit before letting go. Her eye contact will tell you how well your zone is working. (Eyes do this often, but is exaggerated and easiest to see while kissing her hand.) If she looks down or acts shy or girly then your zone is working. She is feels safe and comfortable, and is relaxed enough that even the kiss did not make her tense up. If she breaks eye contact by looking up or rolling her eyes then not only is your zone not working but she thinks you are creepy. (She will probably never change that judgment. Excuse yourself politely. Find someone else with whom to be social. Women who do appreciate your zone are all around. Never waste your time trying to "make it work".)
If she looks sideways or says something as if trying to diffuse tension then she is not sure if your zone is working. This is the difficult response for you because it is not about you. The part of her brain that judges attractiveness is still developing, and she needs time to calibrate it. Do not say anything. Give her a playful smirk and leave. Wait until the next time you see her talk to her again. Perhaps ask, "So, did you decide whether I was very attractive or only somewhat attractive?" As a young man her need for hours or days to do the calibration makes no sense: you naturally know in a moment whether you find any women attractive. As an analogy, consider if you were tasting a very strange flavor of ice cream. Do you like it? It is difficult to decide. You need to consider for a moment. Yet certainly the most alarming and repulsive thing that could happen is if the ice cream suddenly asked you, "So, do you like me?" That would ruin everything.