How to Flirt Online

Last Updated: September 11, 2024

Want to get your flirt on via chat? wikiHow has you covered. You can learn to improve your flirtation and conversation skills online, as well as how to get dates and make connections on the Internet to give yourself the best chance of meeting someone.

This article is based on an interview with our licensed clinical psychologist, Sarah Schewitz. Check out the full interview here.

Part 1

Part 1 of 3:

Chatting Flirtatiously

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1
Start the conversation with something interesting. If you want someone to talk to you, you need to have something to talk about. Whether you know the person in "real" life or just from a dating profile page, it's impossible to find a connection if all you've got to say is "hey" or "ur cute."
- Don't start conversations with, "hey" or "what up." It doesn't give you anywhere to go. Start with an interesting question or an observation, or a comment. ^{[1]
  X
  Expert Source
  
  Sarah Schewitz, PsyD
  Licensed Psychologist
  
  Expert Interview. 15 April 2019.} Even if it's small, start with, "Whoa, whoa-whoa. There's no way I can't ask you about your new profile picture. Is that a waterfall? Please dish."
- Don't start with a line. Innuendo or crude jokes aren't the way to get someone interested. Read the next section for more specific advice for picking conversation topics.
2
Get the other person talking. People like talking when it's easy. If you want to have a fun, flirty conversation, make it easy for the other person to have it by asking them questions and being a good "listener" to their responses.
- Ask lots of follow-up questions. If the waterfall profile picture was in Cancun last summer, ask about the trip. How was it? What was the most ridiculous thing you saw there? Worst thing you ate?
- Don't pry. Asking questions like, "That sounds so fun! I'd be scared to try sky-diving. How was it?" is one thing. But the answer to "How can you afford to sky-dive when you work in the service industry?" isn't any of your business.
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3
Be playful. It's hard to define flirting exactly. Lots of people just want to look for a connection, some kind of electricity. Often, this has to do with your sense of humor and your playfulness. Let your sense of humor come through. If you think it's funny to reference obscure Wu-Tang Clan songs, or random facts while you're talking, then do it. Be yourself. If someone doesn't think that's funny, they're better off with someone else.
- Sometimes, gentle teasing can be flirty and electric, or it can make you come off like a jerk. It might be funny to one person to say, "Whoa nice waterfall picture. That looks cold. Plus those plants are wack. Nice try though." To others, not so much.
4
Respond in a timely way. Flirting needs someone to be at the other end of the line or it won't spark. Respond to as many messages as you can when you see them, and show the other person that you enjoy the exchange between the two of you.
- "Leaving them waiting" is the rallying cry of people with no dates. If you want to chat online, be there to chat. If you want to ignore people's messages, go do something else.
- If someone else isn't talking to you, leave them alone. There's no sense in peppering them with a million interesting and well-formed questions that they're going to respond "lol" to.
5
Be the one who ends the conversation. The best flirtatious conversations end with the other person wanting more. You want to leave them thinking about you, and wishing that you'd log back on for more chatting. Before the conversation runs out of steam, it's a good idea to cut it short and leave them thinking about you.
- Look for a high note that might be difficult to top. If you get someone really laughing, but can't think of anywhere to go beyond that, just end the conversation: "Good talking to you. Gotta feed the dog, though. He's about to eat me."
6
Be persistent . Invest some effort into flirting, but don't expect a lot of return initially until you "click" with the right person. If you can't start a conversation with someone, you can't start a conversation. Flirt around. Have fun. Have lots of conversations, and keep them light.
- On the other hand, don't give up too easily. Online chats can take some time to get to know someone. As mentioned earlier, keep it lighthearted and stay approachable.
7
Stop trying to make yourself look good, and just be yourself. If you want to flirt and find a genuine connection with someone, it's important to be yourself, not the self-promoting Facebook version of yourself. ^{[2]
X
Expert Source

Sarah Schewitz, PsyD
Licensed Psychologist

Expert Interview. 15 April 2019.} It's all too easy to come off as conceited online, the more you talk about yourself and your accomplishments. So don't. Just be you.
- Write the same way you talk. You don't need to make yourself "sound smart" or try to use words you wouldn't normally use to flirt. It'll come off as fake and awkward. ^{[3]
  X
  Research source}
- On the other hand, self-deprecating humor can sometimes be funny, but it can also sometimes come off as desperate or annoying. It's good to talk about yourself in positive ways.

Part 2

Part 2 of 3:

Knowing What to Say

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1
Keep it light. Flirting is just like having a regular conversation, but more fun. Go into expecting that you're going to laugh and you're going to have a good time, not like you're going to get a date with someone, or make them fall in love with you. That's too weird. Just chat like you would with a new friend.
- Take advantage of the Internet as a resource. Just read a funny article or saw a funny .gif or a cute video? Pass it on. Something to share and talk about. ^{[4]
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  Research source}
- Different people like to talk about different things. To one person, it might be flirty to tell long stories and talk about serious subjects, while to another it might be dull. To one person, it might be flirty to talk about partying, while to others it could be a turn-off. Read each person and adjust.
2
Take it slow. Online flirting is a marathon, not a sprint. There's no reason to rush right into talking about what you want, or planning a date, or figuring out where you're going to move in with all the children you're going to have. Whoa there. Just focus on having a few laughs and seeing if you like someone.
- Don't go right for the crude sexual references. Some innuendo can be flirty with the right person, but only once you've gotten to know someone. If it feels pornographic, it's not flirting.
- Avoid blurting out "I love you" on the basis of five minutes of chat and one profile photo. That will be an immediate relationship killer. It's okay to tell the other person that you think they're lovely, fascinating and gorgeous, but leave out love language until you both seem to know each other quite a lot better. If you wouldn't say it flirting in real life, don't say it online.
3
Talk about common ground. If you're in class with someone you're chatting with, talk about class. If you're in the same town, talk about what neighborhoods you like. Talk about the best hang-outs. Talk about something that you have in common with each other to help make a connection. ^{[5]
X
Expert Source

Sarah Schewitz, PsyD
Licensed Psychologist

Expert Interview. 15 April 2019.}
- If you don't have anything in common, or can't figure out what you've got in common, ask questions until you find something. Even if the questions are silly, like, "What's the best month and why?" or "What's your sign?" you'll be able to start talking about something.
4
Talk about something funny that happened to you today. Everybody you talk to online has been fed the same lines at some point, and been asked the same dull questions. "What do you like to do for fun?" and "What are your hobbies?" are sort of dull flirtation questions. But, if you tell a story about how your neighbors are fighting about how the one's dog peed on the other's stoop, you'll have something funny to jump off from. "What do you think of dogs? And ridiculous neighbors?"
- Don't ramble about your own life too much. Talking about your whole history and backstory is a good way to make someone think you're self-obsessed. Share smart details.
5
Don't overshare. Someone doesn't need all the intimate details of your entire life story, your problems, and your innermost thoughts and desires. Save it for later. That's not flirting, it's blurting.
- Don't be a sad-sack if you're trying to flirt. If you've been striking out a lot lately, it won't sound flirtatious to say so. It'll sound desperate.
- Be very, very careful about talking about serious things like marriage, monogamy and having children, especially if you don't know the person. These are all flirt-killing words. Wait until you're in person to talk about these things.
6
Play a silly associative game. If you really can't think of anything to talk about, but really want to be flirtatious, you can always just start playing the random question game and talking about silly things. Talk about your best meals, your favorite animals, whether or not Katy Perry's a genius or more boring than white toast. Good silly questions or prompts to show your funny side:
- "Tell me the story of the best sandwich you ever ate."
- "Which member of the Wu-Tang Clan or One Direction or the Beatles best represents you as a person?"
- "If you could go to any country, what would it be?"
- "What's better, naps or hot-tubs? Or Netflix? Or...hiking? I say hiking, I'm not lazy I swear. Go on, I'm sorry."
7
Compliment the other person, sometimes. Good compliments can be a way to get the door open and have more to talk about. Pick something that you like about the person, or have noticed, and use it as a compliment, then turn that compliment into something you can talk about. ^{[6]
X
Expert Source

Sarah Schewitz, PsyD
Licensed Psychologist

Expert Interview. 15 April 2019.}
- Compliments are nice, but they're also hard to respond to. Try to turn it into a conversation: "That picture of you at the waterfall is so pretty! You look great. What happened that day?"
- One compliment per conversation is appropriate. If you start to seem overly complimentary, it can seem obsessive or creepy. If you think someone is attractive, that's nice to hear, but it's not necessary to say five times every minute.

Part 3

Part 3 of 3:

Getting Dates Online

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1
Sign up for an online dating service . Online dating is increasingly common and almost necessary, especially in bigger cities. It's just the way people meet nowadays. If you want to flirt online and meet exciting people, start a profile on a dating service and start reaching out. It's a good way to get in touch and flirt online. The most popular and common dating sites are:
- Match
- OkCupid
- Tinder
- MeetUp
- Plenty of Fish
- eHarmony
2
Make your dating profile honest. If you want to connect with someone, fill out your profile information honestly and in a flattering way. ^{[7]
X
Expert Source

Sarah Schewitz, PsyD
Licensed Psychologist

Expert Interview. 15 April 2019.} Make yourself sound like the kind of person you are, to attract like-minded people.
- Don't be basic and boring. Every other profile has the phrases, "Living life to the fullest" and "I just like to travel" on it. Be honest and find something interesting to say.
- Think carefully about how you summarize yourself in the profile. Pull out the most distinctive, interesting and true things about yourself to put out there for all to read.
- Honest doesn't mean desperate. If you haven't been on a date in 20 years, it's not necessary to broadcast it for attention.
- Share the interests you're most passionate about. Someone else may just have the same ones!
- Reader Poll: We asked 327 wikiHow readers who’ve dated online, and 59% of them agreed that they look for a common interest to bond over before messaging someone. [Take Poll]
3
Use a flattering profile picture . A connection is more important than looks, it's true. But when you're flirting with someone online, good looking photos of your face and clothed body are still important. If you can't take lovely shots of yourself, have a friend or professional take a few that capture you in your best light.
- Be yourself. Don't try to be the tough, scantily clad, or bizarre version of yourself in your photo. Show yourself as a genuine, regular and likable human being with a photo that shows you at your best.
- No nudes and no drunk pics. Not a good idea.
4
Keep some mystery. There's no reason to over-sell yourself. Keep some privacy, even though you're dating online. Spend a lot of time getting to know someone before giving out intimate details and even then, make the first meetings very public ones. Once you stick to this rule, the rest of your online flirting is about having fun.
- Having someone who seemed nice at first but turns really weird holding your phone number or address is plain creepy, if not downright frightening.
- Avoid any temptation to post hundreds of photos of yourself for people to check out. Anyone you're flirting with will start to think that you're vain.
EXPERT TIP

John Keegan
Dating Coach
John Keegan is a Dating Coach and motivational speaker based in New York City. With over 10 years of professional experience, he runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health.

John Keegan
Dating Coach

It helps to strike a balance between online and in-person dating. Now and then, take breaks from socials and dating apps and try meeting people in person. You never know who you'll meet!

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How can I flirt over text?

Sarah Schewitz, PsyD
Licensed Psychologist
Sarah Schewitz, Psy.D. is a licensed clinical psychologist by the California Board of Psychology with over 10 years of experience. She received her Psy.D. from the Florida Institute of Technology in 2011. She is the founder of Couples Learn, an online psychology practice helping couples and individuals improve and change their patterns in love and relationships.

Sarah Schewitz, PsyD

Licensed Psychologist

Expert Answer

Send them something nice like a compliment! Otherwise, you can always ask about things you have in common to learn more about the other person.

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Tips

Letting the other person be instantly in control of the interaction (and the relationship) comes about as the result of way too many "you're so hot" compliments. Seriously, every idiot is sending the other person these - don't be one of them. If he or she is that hot, guess what? They already know it! So who cares if you message them that, now they know that you're not worth taking seriously.

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When chatting, adding actions let the other person know what kind of person you are. Did they compliment you? Say thank you, and if you are flattered, write *blushes*. The other person can see more of your reaction in your action, so to speak.

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Make sure the person you are flirting with actually wants to talk to you. If they are responding with short one word answers like "ok", then do not try to flirt with this person; they most likely do not want to talk with you.

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Warnings

People lie online. Sometimes you may be disappointed or surprised.

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Always meet in public places until you know each other well enough. In particular, the first meeting should always be in a public place.

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For women, take along girlfriends if you're meeting up at night.

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Don't be creepy. If it is your first time talking to this person you might want to avoid telling them very personal details about yourself or asking them very personal questions.

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Photos of yourself in the 1980s simply reveal that your mentality still rests there. Avoid them like the plague.

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Avoid distance in photos. Let potential daters see you up close.

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Avoid using any photos which feature an ex (or a cropped out ex).

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Steve Santagati, a self-styled dating expert, suggests that women should seek as much personal information as possible about the man while keeping back too much personal information about themselves, as a safety precaution. ^{[8]
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Research source} Whatever your gender, this is sensible advice, you don't want to hook up with a bot, fraud or serial killer. Use instant messaging as a way to get information you need to know. Search the identity online, to see what else you can find out. It is also good to know this person through a friend or someone else to make sure that this person actually exists.

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How to Flirt Online

Steps

Chatting Flirtatiously

Knowing What to Say

Getting Dates Online

Expert Q&A

Tips

Warnings

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