How To Flirt Online

Men's Dating

How to Flirt Online

Kara Pound

Written by: Kara Pound

Kara Pound

Kara Pound is an award-winning journalist based in St. Augustine, Florida. She holds a bachelor's degree in journalism from Flagler College. Her work has been published in INKED, Natural Awakenings, Design Aglow, Memphis Flyer, Jacksonville Magazine, E/Environmental Magazine, and dozens more. Check out some of Kara's work at

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.

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Flirting is a delicate skill to learn. You don’t want to come on too strong or too creepy or downright desperate. Flirting takes finesse and anticipation. You want to lightly touch her hand, smile coyly and make her feel like the only woman in the room. But flirting online is a horse of another color. You can’t utilize tone of voice, facial expressions or body language to help get your emotional intentions across. You have to rely solely on words, abbreviations and silly icons like a happy or sad face.

So, how do you flirt online? Well, guys, here are a few tips to mastering the art of playful behavior — World-Wide-Web style.

1. Be direct.

You have fewer tools to utilize when flirting online. That’s why sometimes the best thing to do is to be direct. Don’t tell her what you mean in 1,000 words or less. Try 10.

2. Be responsive.

Flirting is a two-way street. If you’re into this woman but you’re not getting back to her, then the flirting isn’t going to escalate. It takes two to tango. Make sure you’re writing her back and keeping the momentum going.


“Mastering the art of online flirting

is a necessity in the 21st century.”

3. Be funny.

There is nothing sexier than a guy with a great sense of humor. Most women love to laugh, so show her your funny bone with witty quips and full-length jokes.

4. Be complimentive.

Women love compliments. It can be as silly as “You have a very eloquent way of writing” to “There is nothing sexier than an intelligent woman who is attractive on the inside, as well as the outside.” Either way, compliments are a surefire way to successful online flirting.

5. Be honest.

Just because you’re communicating online doesn’t mean you won’t ever meet in person. Be honest with what you say and how you represent yourself. If the two of you hit it off and you go out to dinner, you don’t want her expecting a 30-year-old man when you’re really 50.

Online dating and all-around communication is gaining more and more popularity these days. That’s why mastering the art of online flirting is a necessity in the 21st century. Guys, stay honest, be responsive, show your funny side and remember, a compliment goes a long way.

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