How to Flirt in Online Dating

Flirting in person is easy. Just flash a playful smile, make some light-hearted jokes, and feed off the energy and you’re off to the races. Flirting online though? Yea, that’s a different story. When you’re hidden behind a computer or phone screen and only have your keyboard to work with, it can feel impossible to know how to flirt.

Good news, though. It’s not impossible. In this guide, we’re going to show you how to flirt online with a new match. We’ll show you the steps and tips you need to know to build attraction and excitement without going overboard and coming across as weird or desperate.

Let’s get into it.

Woman laughing outside

1. Understand that online dating is different than in person.

This might sound like a no-brainer, but it’s an important realization. When you’re just talking to someone online as opposed to in-person, the interaction is going to be (and should be) different. Why is this important? Several reasons.

  • Flirting is much easier in person.
  • The same flirting tactics that work in person aren’t necessarily going to work online.
  • Flirting is (and should be) less intense online than in person.

If you can approach these upcoming tips on how to flirt in online dating with that mindset, it gets a lot easier.

2. Understand the goal of chatting online.

There’s one more thing we need to clear up first. The entire purpose of talking with a new match online is just to build enough interest to get to that first date. You really shouldn’t be talking to people for months online before deciding if you’re interested in moving to meeting in person.

What does this have to do with flirting? Well, if your sole goal is to get to the first date, you don’t need to build a huge amount of chemistry. You don’t need to flirt like crazy and get them to be head over heels for you. All of that can be taken care of in person.

A lot of people who struggle to flirt online are struggling because they’re carrying on too much conversation online. If that sounds like it might be you, your solution very well might just be to shift to the first date sooner than you currently are.

If that doesn’t seem like the case, though, keep reading as we share some tips to help.

3. Exclamation marks and emojis are your friends.

Whether you’re a guy or a girl, using exclamation marks and emojis can be a great way to inject a little excitement into your messages that can come across as flirting. For example, read these two sentences and take note of how they make you feel.

“Hi, nice to meet you. I saw that you’re interested in dogs. That’s great.”

“Hey! It’s nice to meet you 🙂 I saw that you’re interested in dogs. That’s great!”

If we’re being honest, that second message sounds a lot more inviting and exciting. It sounds like one you’d be more interested in responding to. Guess what? That’s flirting. Just by using some silly symbols that make things sound more exciting, you’ve successfully pushed some flirting into your messages.

Here are a few rules to go with this tip, though.

  • Don’t go overboard. Don’t use exclamation marks in back-to-back sentences or with sentences where it doesn’t make sense. If you’re talking about something a little more serious, knock them off.
  • With emojis, stick to those sparingly. Don’t use them with every message. And for the love of everything, keep it clean. Don’t use the eggplant emoji or anything like that.
  • Avoid emojis with hearts or ones that can come across as too serious. You just met this person; don’t scare them away.
  • Don’t feel like because you’re a tough guy that you can’t use emojis. Positivity and emojis are 100% fine for men and women to use.

4. Compliments can make you seem desperate.

For most people who struggle with how to flirt in online dating, their go-to attempt to fix it is to drop compliments. Unfortunately, this just makes you seem desperate and like you’re putting the other person up on a pedestal. It’s okay to be positive and supportive about things they say, but keep the compliments to a bare minimum.

The best way to do this is just to be reactive with your compliments. Don’t lead off with saying that there are things you like or that you think they’re pretty or anything like that. But if they talk about something important to them, respond with something like, “That’s awesome!” or “That’s so cool!”

5. Keep it clean. Seriously.

The other go-to move that people try when they’re struggling with how to flirt online is to get perverted and sexual. In some instances, there is a time and place for this. However, it is overused and inappropriate way more times than it is appropriate. The safest move is to keep it PG, don’t send unsolicited pictures, and don’t force sexual conversation.

6. Remember that jokes may not come across like they do in person.

When you type a message to someone in online dating, they can’t hear you say the message. Often, if you make a joke, it requires the way you say it for it to make sense. This goes for great jokes too! If you are going to say something funny, make sure that it makes sense when read without any voice inflection. A great tip is to read their last message to yourself and then read your message with no voice inflection (monotone) to see if it is still funny.

7. Lols, jks, and hahas are great.

A great way to make sure a joke comes across well is to put lol, jk, or haha behind the comment. It might seem silly but it makes it clear that you’re trying to make a flirty joke.

For example, let’s say that you want to make a joke that their dog looks a little like Albert Einstein. If you just say, “Your dog looks like Albert Einstein,” it could come across as just a weird observation. But if you add some lols, jks, and even some of our earlier tips in, it can sound flirtier and much more like a joke. “Your dog looks like Albert Einstein! Haha!”

8. Positive language is your friend.

With our last example, it may still come across that you’re making fun of their dog which is not effective flirting. One way to combat this is to toss in some overly positive language to support things. For example, ” Your dog looks like Albert Einstein! Haha! That’s so cool.”

Just by adding in that short phrase, we made it very clear that we’re not making fun of their dog but instead pointing out something that we think is cool.

9. Avoid the job interview line of questioning.

When you’re getting to know someone online, it can be tempting to just rattle through a bunch of questions like a job interview. Stop doing this. Yes, it’s okay to ask questions. But ask follow-up questions. Don’t just get into the rhythm of one question, one answer.

For example, if you ask them, “Do you have any pets?” and they say, “Yes, I have two dogs.” Instead of just going on to the next question or talking about yourself, ask them about their dogs. “Awesome, I love dogs! What kind of pups do you have?” Notice how that breaks up the monotony and with the positive language and exclamation points, it’s more fun and flirty.

10. Stop overthinking it.

If you are so worried about putting on a show and impressing someone, you’re going to make mistakes. Online dating is not about impressing someone else. It’s about two people seeing if there is enough of a connection to take the next step. If you take the pressure off yourself, you’ll have better results.

11. Move to the phone or video chat.

If you still want to take some time to get to know them before meeting in person (or they want to), consider talking on the phone or video chatting. While it’s not as good as in person, it’s still an awesome way where you can see and/or hear them. This gives you way more opportunities to feed off of their energy and get some mild flirting in.

The toughest part of flirting online is that you can’t see or hear their reaction to know if it’s working. This helps to change that.

12. The Bottom Line – Focus more on what’s important.

As you can see, most of our how to flirt online tips are more about what you shouldn’t do than they are about what you should do. Why? Well, it comes back to what we said first. The entire point of an online conversation is to get to that first date. In-person flirting is way more natural and is much easier because you can feed off of the natural energy and chemistry.

We share that again because what you should be focusing on is proving that you’re worth a first date, while simultaneously making sure they’re someone you want to spend time with.

The best way to do this is to listen to what they’re saying. Take the time to read their profile. Showcase that you’re genuinely interested in them and not just sending cookie-cutter messages. If you do this and you have a strong dating profile, you’ll be able to get to that first date and kick the flirting into high gear in person—where it matters more.


Written By: Jason Lee

Jason Lee is a data analyst with a passion for studying online dating, relationships, personal growth, healthcare, and finance. In 2008, Jason earned a Bachelors of Science from the University of Florida, where he studied business and finance and taught interpersonal communication.

His work has been featured in the likes of The USA Today, MSN, NBC, FOX, The Motley Fool, Net Health, and The Simple Dollar. As a business owner, relationship strategist, dating coach, and officer in the U.S. military, Jason enjoys sharing his unique knowledge base with the rest of the world.