How to Be Better at Online Flirting

Being a flirt, online or in real life takes a certain level of finesse. Some people are naturally charismatic, effortless flirts. Other people become successful flirts by learning the tricks of the trade through trial and error. Others flirt minimally or not at all. Online flirting is an art form.

I use the term “flirt” very loosely. When I say flirt, I don’t mean cheesy compliments and canned pick-up lines. Saying something like, “There must be a mirror in your pants because I can see myself in them,” is not flirting with another person. That’s just flirting with disaster.

By flirting, I mean the art of witty and spontaneous banter. By flirting, I mean using dialogue and conversation to attract people to you, engaging with people in a light-hearted, fun, easy, and graceful way to bond with them romantically. With the medium of online dating, success necessarily involves utilizing the written word (i.e. your online flirting ability) as a social skill.

Composing a dashing and coquettish message is not as difficult as it seems. Just as there are tips and tricks with flirting in real life, there are rules (and shortcuts) with flirting online. So how do you turn your drab little “Hi, my name is…” message into a sparkling, enchanting, tantalizing series of bon mots sure to send any reader into throes of ecstatic bliss? Harness all your writing ability, and get ready to become a veritable Lord Byron, because it’s not as hard as it seems!  

That’s right. I’m going to tell you how to be betting at online flirting. 

Do not be tempted by the easy compliment or a cliché
It’s too easy, too cheap, to fall prey to the easy compliment and the ready cliché. It’s like giving someone a ready-to-wear message when you can easily whip up some homemade haute couture. Think about it. For this awesome individual whom you’ve set your eye on, getting another message that simply says You’re a hottie or hey what’s up is probably about as exciting as breathing. Online daters are so used to it, they barely notice it anymore. If you choose to compliment, dole out a real beauty, something you’ve thought of and created just for that person. It doesn’t have to be beautiful poetry. All it has to do is not be the same old boring crap this person hears day in and day out.

Metaphors and similes, when used in moderation, are your friends
We are given this thing called language. We should have fun with it! Language serves the purpose of communication, though in the process, we can take all sorts of liberties with it to save it from the abuses of everyday speech. For instance, we can use metaphors and similes. Though it might not be readily apparent at first, the use of metaphor is rife in the arena of the flirted word.

Here’s an example: Guess what my shirt’s made of? Boyfriend material.

Another great prompt for a possible metaphor or simile is You make me feel like… or Around you, I become.

Try it out for yourself. You make me feel like I’m finally home. Around you, I become aware the depths of my own heart. Hey, it’s not so hard!

It’s not the size that matters, but how you use it
Write a sonnet, not a novel. Keep your responses short and sweet—at first. Later on, beautifully articulated, 17-page epics are encouraged. At first, however, you always want to make the person you’re trying to attract lust for more. Give an inch (of prose), and they’ll demand a mile. I’m not a proponent of two-word responses, but a short, two-paragraph message where each word is measured (and no words are wasted) is the online equivalent of a brief conversation that ends too soon and leaves you starving for more. There’s no shame in being coy. After all, isn’t that what flirting is all about?

Don’t reveal too much too soon — mystery is fuel to the fire
In due course, everything will be revealed. If you date someone, they will eventually find out everything about you (the good, the bad, the ugly, and the sublime). Skeletons will eventually tumble from your closets, so there’s no point in disclosing your whole life story too soon. In the art of flirtation, evocative and mysterious statements are the word of law. Your desirability quotient is (at first) at least partly contingent on your ability to evoke a sense of enigma about your persona, to not talk too much or spill too much about yourself in the beginning in order to sustain your date’s sense of interest in you over time. In no sense am I advocating secrecy or lies—it’s important to be honest all the time, less important to disclose information about yourself unprompted and unprovoked. Wait until you are asked, before you spill the beans.

Everyone loves a funny person
You don’t have to be the class clown of online dating, but a little humor never hurt anyone, particularly when used pointedly to attract a mate. Even if it goes against everything you believe, at least try to lighten up and make a joke (think of it as a thought experiment). Humor is like a jolt of charm. Who doesn’t love to laugh? While there is no easy lesson on how to be funny, the best rule of thumb is to try to make it sound natural and situational. Make jokes if it’s relevant and applies, but don’t make stupid jokes for no reason (you’ll come off as a ‘try hard’). This is not to say that you need to take lessons on stand-up comedy in order to date someone. Rather, I’m suggesting that you attempt to see the humor in situations and let your natural humor shine. Everyone out there has a sense of humor. We just have varying degrees of comfort in showing it.

So are you ready to start online flirting? I certainly think so.  Have at it!