How to be a better online flirt

By Juliet O

Being a flirt, online or IRL (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. We use the term “flirt” very loosely. When we say flirt, we do not mean cheesy compliments and canned pick-up lines. Saying something like “there is a mirror in your pants because I can see myself in them” is not flirting with another individual. That’s just flirting with disaster.

By flirting, we mean the art of witty and spontaneous banter. By flirting, we 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 people 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 email 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…” email 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. Here are some tips on how you can use your pen as Cupid uses his arrow, piercing the hearts of everyone around you with the undeniable magnetism and sublimity of your belles-lettres.


Do not be tempted by the easy compliment, the waiting 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 email when you can easily whip up some homemade haute couture. Think about it. For this foxy individual whom you’ve set your eye on, getting another email that simply says “you’re a hottie” or “hey what’s up” is probably about as exciting as breathing. They’re 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 the 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. Like, 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 — just like me,” as silly as it is, is stretching the metaphor of shirt –> boyfriend material –> person who ostensibly wants to be a boyfriend. A great prompt for a possible metaphor or simile: “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

A sonnet, not a novel. Keep your responses short and sweet — at first. Later on, beautiful 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), they demand a mile. I’m not a proponent of 2-word responses, but a short, 2-paragraph letter 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 is 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 Zoosk, 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 is 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.

photo credit: carbonnyc

10 thoughts on “How to be a better online flirt

  1. This process is so frustrating, flirting has always been hard for me and it show with the results I have had. Zoosk has only showed me less than desirable women. What does it take? I have flirted with 40 women and one response. All I ask is respond and say your not interest or don’t post on sites like this. Nice guy tired of finishing last.

  2. I like this post.
    Mystery and Humor can be a deadly combination if used in the right amount.
    If you joke too much and acting too funny, it’ll seem like you are immature. And by too much mystery you will look uncommunicative.
    Find the right balance.

    Aidan C

  3. Pingback: It’s my Zoosk in a box « Zoosklog – Online Dating Blog by Zoosk

  4. Excellent list. I would, however, add one more major, though rare, turn-off in online communication: Excessive formality. I learnt English from books and law – and it shows. An instinctive capitalisation of You is just one example. A certain pedantic drabness of language is another. In effect, you aren’t drafting a company statute, and your language should be at least slightly warm.

  5. I love this list, thanks for sharing it.

    One thing I would really like to know is, can you learn how to become funny. I know being funny helps with flirting and confidence, but can you learn it. I read this article http://hubpages.com/hub/How-To-Be-Funny-All-The-Time but I’m still not convinced.

    I know this is where I struggle in relationships, I hate being boring =[ How do i become the ‘funny guy’

    Would love a response, and thanks again for the list.

  6. I think this is where I struggle in the online world, my flirting skills are rather terrible to say the least.

    “Don’t reveal too much too soon — mystery is fuel to the fire”

    And that quote is so true, I will think of that when I’m dating.

    Thank you.

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