How to Flirt via Text

Recall the last time you had a “crush” that sent you text, asking to hang out.

“Wanna hang out l8r? Ppl r coming over my house, would like 2 c u there :-)”

Your stomach is in knots and a wide grin spreads across your face. He wants to hang out with me?

Of course, you’d like to go, but you’ve already made plans with Cindy. So, you try to continue the conversation, letting him know you’re interested without being aggressive. But, how do you do that?

The simple solution to any text message flirting is the emoticon, with the winking emoji winning the title of “THE flirty smiley.” Adding an emoticon to any text message automatically lightens the mood, but when texting with a person of interest, the proper emoji has the power to transform the conversation, hopefully working in each party’s favor.

Emoticons are funny, in the sense that they can communicate so much, by sending so little. But, just like with everything else, there’s a proper way to use them, and a way to avoid. The most important mistakes to steer clear of are sending too many emoticons and overusing the winking emoji, which can have a negative connotation. Note the difference between these texts;

“Sure, I’ll come over later.”
“Sure, I’ll come over later ;-)”

I probably don’t need to explain why the latter text sounds suggestive.

Or, note the difference in these texts;

“Sure, I’ll come over later :-)”
“Sure, I’ll come over later 🙂 🙂 🙂 🙂 :-)”

The latter text appears slightly psychotic, as you can see.

So, how do we use emojis to flirt?

When Johnny first sends his invite text, he included a smiley at the end of the sentence. This smiley communicated a friendly, inviting vibe, which would immediately have changed if the smiley were winking or crying. This is a positive way of informing you of his excitement to see you, without appearing excessive. Respond in the same manner.

“I’d like to hang out, but I made plans with Cindy already. Maybe tomorrow? :-)”

The smiley face Johnny know that you aren’t brushing him off, and that you’re excited to see him as well. However, don’t continue the texting game by including emojis at the beginning, middle or end of every sentence. That’ll appear a bit much.

Fast forward two months from now. Johnny invites you to an exquisite dinner overlooking a lake. You purchased a new sundress for the occasion, complete with a new hairstyle. After the date, he sends you a text;

“You looked beautiful tonight.”

Overcome with excitement, you want to respond accordingly, without letting him know that you’re melting. Here, the winking face can make good use.

“Thanks. You didn’t look too bad yourself ;-)”

Coy, but not suggestive or clingy. That’s the best way to text using your trustee emoticons. Always remember, less is more.

If you have earlier versions of Android devices, which lack all the interesting emojis, I suggest you download an emoji application. Trust me, they’ll come in handy.

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6 comments
  1. After I originally left a comment I seem to have clicked the -Notify me when new comments are added-
    checkbox and from now on whenever a comment is added I receive
    four emails with the exact same comment. Perhaps there is an easy
    method you can remove me from that service?
    Many thanks!

    • Sure I’ll take a look! I’m really not sure exactly how to remove this option though. Have you revisited the location of your comment and unchecked the option under the blog post?

  2. Escapist Theory, this was a tough one to critique because copy and paste in wordpress doesn’t allow for emoticons to show up and I had to keep referring to the original text above. I like the topic you chose to cover. It’s synonymous with your voice and helpful to those that are still new to them, or the dating scene in general. Mine has nothing to do with my voice, which makes me question it. The examples you used are great. Keep in mind the parenthesis are only suggestions. Good job!

    Recall the last time you had a “crush” that sent you (a) text, asking to hang out.

    “Wanna hang out l8r? Ppl r coming over my house, would like 2 c u there ”

    Your stomach is in knots and a wide grin spreads across your face. He wants to hang out with me?

    Of course, you’d like to go, but you’ve already made plans with Cindy. So, you try to continue the conversation, letting him know you’re interested without being aggressive. But, how do you do that?

    The simple solution to any text message flirting is the emoticon, with the winking emoji winning the title of “THE flirty smiley.” Adding an emoticon to any text message automatically lightens the mood, (start a new sentence here) but when texting with a person of interest, the proper emoji has the power to transform the conversation, hopefully [working in each party’s favor] (for the better).

    Emoticons are funny[,] in the sense that they can communicate so much, [by sending so little] (sounds awkward. Try something like, “…can communicate so much in one single character”). But, [just] like [with everything else] (most communications), there’s [a proper way to use them, and to avoid] (effective ways to use them, aw well as common mistakes that convey the wrong message). The most important mistakes to steer clear of are sending too many emoticons and overusing the winking emoji, [which] (This) can [have a] (send) negative connotation(s). Note the difference between these texts;

    “Sure, I’ll come over later.”
    “Sure, I’ll come over later ”

    I probably don’t need to explain why the latter text sounds suggestive.

    [Or, note the difference in these texts] (Here’s another example of using emoticons effectively);

    “Sure, I’ll come over later ”
    “Sure, I’ll come over later ”

    The latter text appears [slightly] psychotic, [as you can see]. (Who would possibly want this person to come over?)

    So, how do we use emojis to flirt?

    When [Johnny first sends his] (you initially receive Johnny’s) invite text, [he included] (with) a smiley at the end of the sentence (, take that smiley for what it is:. [This smiley communicated] a friendly, inviting vibe,(end sentence here) [which would immediately have changed if the smiley were winking or crying]. (I would suggest moving this part to the end of the paragraph for more of a distinct comparison) This is a positive way of informing you of his excitement to see you, without appearing excessive. Respond in [the same] (a similar) manner (like this:).

    “I’d like to hang out, but I made plans with Cindy already. Maybe tomorrow? ”

    The smiley face (lets) Johnny know (two things:) [that] you aren’t brushing him off, and [that] you’re excited to see him as well. [However, don’t continue the texting game by including emojis] (While this emoji works great here, try not to use them excessively to avoid overkill) [at the beginning, middle or end of every sentence. That’ll appear a bit much.]

    Fast forward two months from now. Johnny invites you to an exquisite dinner overlooking a lake. You purchased a new sundress for the occasion, complete with a new hairstyle (and shoes to match – adding something else here brings home the word ‘complete’). After the date, he sends you [a] (this) text;

    “You looked beautiful tonight.”

    (Though you are) Overcome with excitement, you [want to respond accordingly, without letting] (don’t necessarily want) him know that you’re melting. Here, the winking face [can make good use] (is appropriate).

    “Thanks. You didn’t look too bad yourself ”

    (By using this emoticon, you are being) Coy, but not suggestive or clingy. [That’s the best way to text using your trustee emoticons.] Always remember, less is more.

    If you have earlier versions of Android devices, [which lack all] (without) the interesting emojis, [I suggest] you (can always) download an emoji application. Trust me, they’ll come in handy.

    • Thanks! This was one of my favorite posts so far, because of how familiar I’ve been with the topic! (Not to mention, the use of emojis was fun).
      What I enjoy about your critiques is that you suggest ending sentences earlier than I’d normally be inclined to do. But, the effect is much stronger. Sometimes ending a sentence with one thought rather than two or three thoughts makes the statement stronger. The reader can focus on that one thought rather than several thoughts simultaneously.

      • Yes, making shorter sentences was yet another BIG concept I’ve taken away from Zinsser. It does exactly as promised. We’ve just been taught for too long that big words and lengthy sentences make us seem superior to our readers, when they really confuse the sh*t out of them! Thanks – I love your work & writing style 🙂

      • Thank you! And I’m a fan of your writing style as well! I struggle with the bigger-sentences-bigger-words superiority complex. This class has really helped me learn how to tackle this issue.

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