How To Flirt With Men Online

Women's Dating

How to Flirt With Men Online

Sam Stieler

Written by: Sam Stieler

Sam Stieler

Sam has been writing about dating and relationships for more than three years now. He holds a bachelor's degree from Bucknell University, has self-published a few of his own books and is currently working on mastering the double right turn in his salsa dancing classes.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

Discuss This! Discuss This!
Advertiser Disclosure

Flirting online can be very, very difficult. The Internet is still very much a typed medium, and the nature of flat, expressionless text makes it difficult to engage in the light, winking, double-entendre filled practice of flirting. Good flirting relies on toying with the meaning behind words, and conveying precise meaning through flat, expressionless text seems to render online flirting impossible.

Of course, flirting online isn’t actually impossible. In fact, flirting online doesn’t even need to be particularly difficult. As long as you keep a few points in mind, you won’t have any trouble making it clear there are worlds of meaning behind every online message you send a guy.

Let’s talk grammar.

How do you make it clear you’re flirting with a man when you speak with him in person? Chances are, you change the tone of your voice and the cadence of your sentences. In other words, when you start verbally flirting with a man, you slip into an alternative way of talking, one that’s obviously and demonstrably different than how you speak during “normal” conversation.

When you flirt online, you need to use an alternative way of writing. You need to type differently than you do during your “normal” online communication. If you type up your flirtations in a simple, clear-cut, direct and to-the-point manner, a guy will take what you say just as seriously and bluntly. But if you change the cadence of your sentences, and if you change the tone of the words you use, he will know you’re flirting.

For example, one of the best ways to type flirtatiously is to use ellipses, those rows of three periods that leave sentences hanging while opening up lingering spaces between your words — spaces where alternative meanings and all sorts of delicious assumptions can fall.


“Simply put, just as offline flirting happens anywhere

and everywhere, online flirting can occur

anywhere you want to engage in it.”

To emoticon or not to emoticon?

Emoticons have developed a bad rap among people of a certain age and level of assumed “maturity.” That’s because many of us used emoticons when we were younger, when we first started chatting away online, and we continue to associate those little smiley faces and winking yellow dots with a juvenile form of flirting.

But let’s be honest — flirting is always at least a little juvenile (that’s part of the fun!) and we used emoticons in our chats when we were teenagers because, when it comes to making an intention clear, emoticons work.

Think of emoticons as a new form of punctuation. You don’t want to go overboard with your emoticons any more than you want to send a message online with a dozen exclamation points tacked on to the end. And like proper punctuation, an intentionally placed emoticon can radically change the tone and intention lying behind every message you send.

Where to flirt online?

Now that you have some idea of what it takes to flirt online, you likely have a single remaining question: Where online should you flirt? Are some online platforms inappropriate to send a flirtatious message on? Or is every website fair game to play on with your man?

Simply put, just as offline flirting happens anywhere and everywhere, online flirting can occur anywhere you want to engage in it. There are a few exceptions, but as long as the messages between you and your man are private, then there’s nothing more inappropriate about sending a flirty message to his email while he’s at work than sending him a flirty text message whenever you want. As long as you respect his public professional image, all online channels are open for a little fun.

Advertiser Disclosure is a free online resource that offers valuable content and comparison services to users. To keep this resource 100% free, we receive compensation from many of the offers listed on the site. Along with key review factors, this compensation may impact how and where products appear across the site (including, for example, the order in which they appear). does not include the entire universe of available offers. Editorial opinions expressed on the site are strictly our own and are not provided, endorsed, or approved by advertisers.

Our Editorial Review Policy

Our site is committed to publishing independent, accurate content guided by strict editorial guidelines. Before articles and reviews are published on our site, they undergo a thorough review process performed by a team of independent editors and subject-matter experts to ensure the content’s accuracy, timeliness, and impartiality. Our editorial team is separate and independent of our site’s advertisers, and the opinions they express on our site are their own. To read more about our team members and their editorial backgrounds, please visit our site’s About page.