Let me just admit right away that I am a flirt. But I didn't start off like this; I wasn't born with the skill to flirt. A late bloomer (and an anthropologist by nature), I studied flirting avidly. Close friends who already had the knack were always a good source, and from there I experimented as much as I could. (Frankly, I'm surprised that I haven't written a treatise on the Universal Theory of Flirtatious Behavior yet. Hmm, now there's an idea for my senior project...!) So you can skip the studying if you continue reading below.
But there's a big catch-22 about flirting: if you don't do it a lot, you probably won't be good at it, but if you're not good at it, you probably won't do it a lot. From friends of mine who were mystified by the intricacies of flirting, I've come to realize that it isn't as obvious as we often make it out to be. So here is the information that can get you started on being a great flirt, de-classified and as straight forward as possible, but you'll have to work out the kinks for yourself.
First, some quick info for the noobs:
Kossacks Under 35 is a weekly diary series designed to create a community within DailyKos that focuses on young people. Our overall goals are to work on increasing young voters' Democratic majority, and to raise awareness about issues that particularly affect young people, with a potential eye to policy solutions. Kossacks of all ages are welcome to participate (and do!), but the overall framework of each diary will likely be on or from a younger person's perspective. If you would like more information or want to contribute a diary, please email kath25 at kossacksunder35 (at) gmail dot com.
Four things to remember:
1 - Flirting is, first and foremost, a way of making the other person involved feel good. Ideally, they will return the favor, but you should still think of it more as a no-strings-attached gift than a favor. (Expecting something in return will make it seem like you are doing it just to get compliments, and no one likes a person who is that selfish.)
2 - Flirting is not an agreement to have sex. A lot of men (and some women) misinterpret flirting as a green light for sex when it is not.
3 - "When you first meet new people, their initial impression of you will be based 55% on your appearance and body-language, 38% on your style of speaking and only 7% on what you actually say."
4 - This is all from one person's experience, so not only is there a huge chance that at least one person will disagree with me, I hope anyone who does will tell us about their experiences.
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There was actually another diary about flirting that appeared before this one, just two weeks ago in fact. It's got some great advice but I don't think it quite gets to the true meat of flirting. Sure, you've got to be sincere and have a good sense of humor and all that, but in my not-so-humble opinion, the essence of flirting is what you say and how you say it.
How you say it
The most important part, but the part that so many people get wrong, is body language. It is largely unconscious in most people most of the time (including myself), so even if you can't figure out from a person's tone or words what they are really thinking, you can figure it out from their body language as long as you know what to look for.
My dad, a former cop, was the one who taught me the importance of body language in general. I remember him demanding that I uncross my arms once when I was 14 and pissed off at whatever discussion we were having; he knew that uncrossing my arms would force me to listen to what my parents were saying, since the way we position our bodies can have as much impact on how we are acting as it can on sending different messages to other people.
We're not interrogating anyone when we flirt, but it's very useful for something equally as interactive. If you train your body to say the right things even while your mouth is stumbling, you can still make the person feel good. And you can use it to see how your flirting partner is responding, as well as to modify your own behavior if you want to.
This is the least important part of your body when it comes to flirting. In fact, when you're flirting, the best thing to do is forget that you even have a lower body. There are at least three different kinds of horniness: genital horniness, love horniness, and brain horniness. Flirting is all about stimulating the brain and the heart. So even if it pleases your nether regions, flirting and sex are only distant relatives.
If you keep your hands visible most of the time, you're telling the person that you're comfortable with them and not going to be secretive. In my experience, if you're standing and put your hands all the way in your pockets, that means you don't have anything to say at the moment and aren't entirely comfortable with silence. The openness of the hand can indicate the openness of the person; in other words, interlocking your fingers says, "I'm still not completely sure about you" while keeping your fingers outstretched says, "I'm so into you." Setting your chin in your hand while making eye contact is a good way to make sure your body is flirting as much as you are; it makes you lean forward and basically says, "I'm yours." Also, the more you fidget with your hands, the more you're going to look like you just can't wait to get out of there... which can be a good thing if, say, you've both decided that you're going to go have some clothes-ripping sex as soon as you've paid the bill but can be a bad thing if you don't have any continuation plans. If you're nervous, wiggle your toes or flex a leg muscle or something.
But your arms are important too. What you do with your arms generally determines what you will do with your torso, and your torso is a big part of the whole impression. Leaning towards someone shows extreme interest. You've probably seen lovers do it; they'll lean in close and you can just tell that they don't see anyone else in the world. On the other hand, sitting up straight conveys reservedness, while leaning away from the person can mean either "I'm really not into you" or "GOOD GOD PLEASE GET ME OUT OF HERE". Okay, I'm kind of exaggerating that last one but at least you get the idea of the spectrum of meaning. If you cross your arms in any way, the message you'll send will be, "I need a little distance" or even "I don't care." I've seen people keep their arms straight but twist them while clasping their hands and hiding them under the table; while you might figure that this would mean a combination of all the above, it actually seems to mean that they have a secret that they're afraid to tell you.
Finally, hunched shoulders show a lack of confidence, but confidence is what seems to attract people the most. Keep your posture as straight as possible without resorting to stiffness.
Supposedly, women will chew on their lips or lick their lips more when they are flirting with someone. Frankly, I think this is crap that comes from too many movies with male directors who think that this is how women should or do flirt. But in real life, women (and men) are often too busy doing things with their mouths like chewing food, talking, smiling or laughing to do the cutesy bombshell-with-a-finger-between-the-lips thing. The importance of the mouth comes in the smile, plus whatever other cues are accompanying it. If a smile is accompanied by the person leaning forward and making strong eye contact, you're doing great. With shy people, or some women who don't think they should be too forward, they may flash a smile briefly before looking away again; as long as their whole face is involved, you're probably doing just fine. If the smile is short and only in the mouth, they're being polite while also trying to think of a legitimate excuse to leave. Beyond that, the mouth is only secondary to a lot of other methods of flirting with body language.
I've read that women will supposedly play with their hair when they are interested, and I also think this is crap (as well as everything else on that webpage!). Personally, once I've got my hair fixed, I don't mess with it, unless I want to have to run to the bathroom to fix it every 10 minutes. Other than Ann Coulter (shudder) and the annoying popular girls in high school who wore their hair like Ann Coulter, I've never even seen a woman toss her hair around much. Other motions, like running her fingers through the ends or twirling it around her finger, actually signify distraction to me; she's much more interested in whether her hair is tangled than in whatever it is you are saying. And to keep this totally balanced, I've never seen a guy play with his hair while flirting either.
Eyes are the most important part of flirting. Flirting without your eyes would be like breathing without your lungs; it just wouldn't work. I believe there have been studies that show that humans can read the expression of other humans by only looking at their eyes; no other body part is that expressive. In fact, I'm not going to elaborate on everything that every slight eye movement could mean because it would take me a week and I think you guys can probably figure it out for yourselves.
Eye contact is vital, but the amount of continuous eye contact is important as well. You should never stare at someone for an extended period of time unless you're in training to be Big Brother. One of my close friends once told me that he watched a girl sleep all night, then told her in the morning. I know he didn't mean anything creepy by it, but the girl never called him again, and I can't blame her. If you don't understand why this would be a problem, ask someone to stare at you for 10 minutes straight, without looking away. In other words, do not forget to intersperse eye contact with looking away; generally, if the other person looks away, you should look away for a moment too.
What you look at is generally important as well. You absolutely should not look away at a part of the other person's body that is considered sexual, unless you are actually going to proposition the person! Even a glance at my boobs has sabotaged many men's chances with me because it gives the message that that is where their interests lie. I've also had this experience: I make eye contact with someone across the room and we start flirting. One of my male friends that I'm hanging out with says something to me and so we engage in conversation for a few minutes, with me looking at him the whole time. But I talk to my friend for too long, and by the time I look back at the guy I was flirting with, he's already decided that my friend is actually my boyfriend, since I didn't look back fast enough. Because I was looking at my male friend for so long, and didn't pay enough attention to the guy I was flirting with, the latter ended up thinking that that was my non-verbal way of indicating that I was already involved with someone else.
Touching the other person is probably the clearest statement you can make without saying anything. Employing this too soon (or artificially) can derail the whole thing, but different people are so different about acceptable timing, I can't tell you exactly when the best time to do it is. I suggest you try it only if all the other signs are there and you are almost positive the other person is not only interested in you but possibly interested in taking it beyond just a simple flirtation.
I also include how close you are spatially as touching, since moving into someone else's comfort zone can have the same effect as actually coming into contact with them. This is tricky, too, since different people have different comfort zones. In a very general way, the further east you go in America, the closer people will stand to you when you are talking. In my experience, also, the relative size of the spaces available wherever the person grew up will determine how close they will stand, so that someone from a crowded European city will often stand closer than someone from rural America. It is usually pretty easy to tell how uncomfortable you are making the person, though, because serious violations of personal space are usually met with abrupt moves, whereas you may not even notice at first if you've accidentally gotten too close but the person doesn't consider it too forward or an awkward proximity. As with physically touching, I can't tell you the exact moment when moving closer is a good idea, but the best way to tell is that the person somehow repositions themself closer to you without any apparent thought about it.
What you say
I wish I could just tell you that it didn't matter what you say as long as your body language is good, but unfortunately, it does matter. Once the conversation has begun, you should switch between one of the below and just regular talk punctuated with interested body language; if you talk about the other person too much, you can come across as too aggressive or slick, or as if you are trying to hide something about yourself. Also, if the conversation doesn't flow, the flirting probably won't either.
Complimenting a man or woman you've never met before is basically the same: don't compliment them physically. The only times I can think of when this rule doesn't apply are when you're talking about something like strength or if the person has a tattoo on a fairly neutral part of their body.
Here's a short but good article on giving a good compliment. If you don't know how, I would suggest practicing on people who already know you first, since they will be much more keen on giving you constructive criticism than a total stranger.
In short, ask the person about themself. Make sure the questions fit in with the conversation you're already having. Asking questions shows that you are interested in them as a person. In my experience, if you're asking something that may cross the line into being too personal for how well you know each other, you can just say so and make sure you have a backup subject if they don't want to. Giving them the space to avoid uncomfortable questions without making the situation awkward is very considerate. In general, though, you should avoid the heaviest questions, ones that could potentially bring down the mood of the conversation, until you know each other pretty well.
Essential but tricky, jokes are a good way to see if you are compatible or not. Everyone has a sense of humor, but not all humor is the same. Some people love puns, while others will just groan and roll their eyes. Jokes take a lot of confidence because of the possibility that they will fall flat, but that can be a good thing; even if they don't like the joke, they still might like the fact that you had the guts to try it.
What is the coolest thing about you? What about yourself are you most proud of? What do you like to do in your free time? You're basically selling yourself when you're flirting, so highlighting your best qualities is a good thing. Too much bragging can make you seem full of yourself, but too much humility can make the person think that you might not have any good qualities that you can play up.
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Finally, while most people talk about flirting as if it is something that is only necessary at the very beginning of a relationship, I firmly believe that flirtation is important throughout a relationship. Once you've snagged your special someone, you don't want them to feel any less special. So the rules may be different (you don't have to worry as much about scaring them away) and you probably won't flirt with them as much as you did in the beginning, it's never a bad idea to make the person you love feel awesome by flirting with them a little bit.
If you want to know more (because I'm sure I left a lot out), you can either ask me or read this excellent article that I had a hard time not plagiarizing.