4 Ways To Flirt Through Text Messages - WikiHow

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How to Flirt Through Text Messages Download Article Co-authored by Joshua Pompey

Last Updated: June 5, 2025 Approved

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• Have a Flirty Opening
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• Keep Your Crush's Attention
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• Finish Strong
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• How Do You Flirt Through Text Messages?
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• Flirty Text Message Help
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• Video
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• Expert Q&A
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This article was co-authored by Joshua Pompey. Joshua Pompey is a Relationship Expert and Founder of Next Evolution Matchmaking (NEM) based in New York City, NY. With over 15 years in the industry, Joshua helps his clients navigate online dating and has a success rate of over 99%. His work has been featured in CNBC, Good Morning America, Wired, and Refinery29 and he has been referred to as the best online dater in the world. wikiHow marks an article as reader-approved once it receives enough positive feedback. In this case, several readers have written to tell us that this article was helpful to them, earning it our reader-approved status. This article has been viewed 4,111,639 times.

In today's technologically advanced society, you may spend more time texting your crush than actually hanging out with him or her. This means that you should not only be able to flirt with your crush in person, but through your text messages. If you want to flirt through texting, you have to know how to be playful, witty, and charming in just a sentence or two. Read on from step one below.

Steps

Method 1 Method 1 of 3:

Have a Flirty Opening

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1. 1 Be creative. It's hard to be original when you're texting, so the person you want to flirt with will be even more impressed when you're able to pull it off. When you pull out your phone to text that special person in your life, you should try to think of something no one else but you could say. This will pique the interest of your crush and will make him more likely to respond to you right away.
   • Make your crush laugh. Start off with a short funny statement about something you both saw recently, or referencing a previous conversation.[1]
   • Make a clever observation. Your crush will certainly respond to that. Flirting with your wit is a great tactic.
   • Be original. Write something that no one can say but you.
   • Wondering how to flirt over text? Check out wikiHow’s “How do you flirt over text? I’m so bad at it” forum!
2. 2 Ask an open question. An open question is one the other person cannot answer by just saying yes or no. Asking an open question is a great way to impress and flirt with your crush because it shows that you're not texting just because you feel like it, but because you want to keep a conversation going and care what your crush thinks. Here are some great things to keep in mind when you ask questions:[2]
   • Keep it simple. Just ask about something that happened during that person's day or week, like how her friend's birthday party went or if her mini vacation was as fun as she had hoped.
   • Ask lots of open-ended questions. Don't just ask a question that can be answered with a simple "yes" or a "pretty good." Give your crush room to elaborate and to ask you something back.
   • Don't be too open-ended. Don't ask a deep philosophical question that your crush doesn't know how to answer. They may be puzzled by your message and could just give up.
   • Don't be a boring texter. You're less likely to get a response if you say something like, "What's up?" or "How are you?" Be original, even when you ask questions.
   • Be thoughtful. If you know your crush had an important event the day before, a text asking how it went shows that you pay attention.
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3. 3 Watch your spelling and grammar. This may seem silly and irrelevant, but if you were flirting with your crush in person, then you would make sure your outfit was neatly put together and that your hair was in place. Therefore, if you're sending a text message, you should make sure you're using proper punctuation and that your sentences are complete.[3]
   • If you send sloppy or inarticulate texts, it will look like you don't care enough about the person you're texting to spend enough time scanning your texts.
   • Your writing doesn't have to be perfect. Just skim each of your texts once before you send it.
4. 4 Don't come on too strong. Subtlety is key when you're opening up a text-based conversation, so you should try not to go overboard, or your crush will be able to see that you're trying too hard from a mile away. Just relax and send a text when the time feels right, and don't overthink it. You shouldn't spend more than a minute deciding what's the best text to send your special someone.
   • Make sure you're not always the person who sends the first message. If you are, then your crush may not be so excited to hear from you. Play it cool and wait for your crush to chat with you first sometimes.
   • Don't try too hard to be funny. If your target can tell you spent hours crafting the perfect opening, it's not worth it.
   • Remember that flirting over text is not so different from flirting in real life. You should still relax and take it easy if you want to be a successful flirt.
   EXPERT TIP

   Joshua Pompey

   Dating Coach Joshua Pompey is a Relationship Expert and Founder of Next Evolution Matchmaking (NEM) based in New York City, NY. With over 15 years in the industry, Joshua helps his clients navigate online dating and has a success rate of over 99%. His work has been featured in CNBC, Good Morning America, Wired, and Refinery29 and he has been referred to as the best online dater in the world. Joshua Pompey Dating Coach

   Don't wait several days to text someone after a date. There's no reason to wait two or three days to contact the other person because these days, everyone has their phones on them. You have ample opportunity to talk earlier.

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Method 2 Method 2 of 3:

Keep Your Crush's Attention

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1. 1 Tease your crush. Teasing over text is a great way to flirt with your crush. You can be a little bit playful and make fun of your crush, and let your crush make fun of you back. This shows that you don't take yourself too seriously and that you're invested in the person you're texting.[4]
   • Keep it light. Tease your crush for watching a silly movie or spending too much time with his guitar.
   • Make sure your crush gets that you're joking. It should be clear that you're not trying to be offensive and that you just want to have some fun.
   • If you have a silly nickname for your crush, use it when you're texting.
   • Send a wink face emoticon to show that you're just teasing.
2. 2 Show your crush you care about him. If you want to flirt through texting, then you should find a way to make it clear that you care about the person you're talking to, whether it's by asking a question about his life or just asking how he's feeling.
   • If your crush is feeling sick, check in to see if he's feeling better.
   • Use your crush's name occasionally. This will surprise and excite the person you're texting.
   • Ask your crush's opinion on a new movie or restaurant. This may even turn into plans to check out the new event together.
   • Compliment your crush. Find a subtle way to let her know she looked cute the other night, or that you liked her new haircut.
3. 3 Be a little naughty. You can find subtle ways to arouse your crush through texting. You don't have to say, "What are you wearing?" to show that you're thinking about your crush in a less-than-PG-rated manner. Here are some tricks to try:
   • Casually mention that you just got out of the shower.
   • Be open. Just say, "I can't stop thinking about that dress you wore the other night."
   • Say, "I have a bottle of wine in my fridge, and it looks so lonely without you." Inviting your crush to share a bottle of wine is an invitation for more.
4. 4 Don't be too eager. Remember that you're supposed to play it cool when you're texting, so you shouldn't be the person who sends a hundred questions in a row or asks a question with a million question marks. If you're too excited about texting the person on the other end of the conversation, it will be a major turn off.
   • Make sure that you and your crush roughly text each other the same amount of times. If you send her five texts for every one of her responses, you have a problem.
   • Emoticons are great for occasional flirtation, but don't overuse them. The same goes for exclamation marks and questions.[5]
   • Don't respond the moment you get a text. Play it cool and wait a few minutes, or even a few hours, to respond unless the text is time-sensitive. If your crush takes a day to get back to you, don't fire back a text right away or you'll look desperate.
   • Reader Poll: We asked 900 wikiHow readers what do they do when a crush doesn’t respond to a text, and 57% said they would wait patiently for them to reply. [Take Poll]
5. 5 Don't use texting to build a meaningful connection. No relationship is made or broken through a series of text messages. When you text your special someone, remember that texting is a great way to flirt, to make plans, and to take the relationship into the physical world, but not a great way to build rapport or to really get to know someone.
   • Remember to keep it light. Flirting is all about having fun and being playful, not about getting into a deep discussion.
   • If you really like the person, try to spend more time talking to them than you do sending text messages to that person.
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Method 3 Method 3 of 3:

Finish Strong

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1. 1 Know when it's time to stop texting. You don't want to be that person who keeps up a textual exchange hours after there's nothing left to say. When you're talking to a new love interest at a bar, you should talk just long enough to hook the person and then say you have to leave so you don't drag out what started off as a good conversation. Well, the same goes for texting.
   • If you're doing most of the talking in a textual exchange, it's time to stop texting.
   • If you keep sending long messages and getting nothing back but one-word answers, then it's time to stop texting.
   • If you can just feel that both of you are struggling to find something to say, then it's time to end the conversation.
   • If you have the sense that you're doing most of the talking every time and that the person you're texting doesn't seem too eager to get back to you, it may be time to end the conversation -- for good.
2. 2 Leave on a good note. Whether you're just stopping the conversation because you're busy or because you're going to meet up, you should leave the person you like with something to think about. Don't just say, "Bye!" or that person won't be thinking about you after you stop texting.
   • If you're meeting up, don't be afraid to say that you can't wait to see that person.
   • If you have to go, tell the person where you're going and what you're doing. This will make you look like you have a great life outside of texting and will intrigue the person on the other end of the conversation.
   • Leave an opening to pick up the conversation at another time. Say that you're looking forward to chatting about whatever is on your minds later.
3. 3 Use your texts as a way to ask your crush out. If your texting sessions have been going really well and your flirting is getting fierce, then you should take your relationship to the next level and use texting as an opportunity to ask the person out.
   • Keep it light. If you're in the middle of a conversation, just say, "How would you like to pick this up over dinner or drinks?"
   • If you've really been texting the person a lot, you can say, "I really like texting you, but I think I would like talking to you even more. How about we continue this in person?"
   • You can also be more casual. Instead of asking for a real date, you can invite the person out to join you and your friends for drinks or at a party.
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How Do You Flirt Through Text Messages?

Flirty Text Message Help

Common Flirty Phrases Sample Emoticons

Improve Your Texting Game with this Expert Series

Are you not sure what to text girls, or do you find yourself getting ghosted? We’ve put together this series of expert articles to help you text easily and confidently. 1 Text a Girl You Just Met 2 Flirt Through Text Messages 3 How to Know When and How Often to Text After a First Date 4 What Does It Mean When a Girl Says She's Sorry for the Late Reply? (and How to Respond) 5 How to Respond when a Girl Says She Likes You over Text 6 Persuade a Girl over Text

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• Question Is it OK to send flirty texts? Joshua Pompey Dating Coach Joshua Pompey is a Relationship Expert and Founder of Next Evolution Matchmaking (NEM) based in New York City, NY. With over 15 years in the industry, Joshua helps his clients navigate online dating and has a success rate of over 99%. His work has been featured in CNBC, Good Morning America, Wired, and Refinery29 and he has been referred to as the best online dater in the world. Joshua Pompey Dating Coach Expert Answer Yes, it is fine! Just try not to be clingy. Text at intervals, so you are not overbearing and leave the person thinking about you and wanting more, but at the same time, don't disappear altogether. Thanks! We're glad this was helpful. Thank you for your feedback. If wikiHow has helped you, please consider a small contribution to support us in helping more readers like you. We’re committed to providing the world with free how-to resources, and even $1 helps us in our mission. Support wikiHow Yes No Not Helpful 12 Helpful 36

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Tips

• Make sure you send it to the right person Thanks Helpful 1563 Not Helpful 245
• Don't say anything you wouldn't say in person. Being too open while texting makes things awkward in person. Thanks Helpful 1226 Not Helpful 216
• Don't re-send messages. Getting the same message 8 times gets really annoying. Thanks Helpful 1147 Not Helpful 229

Show More Tips Submit a Tip All tip submissions are carefully reviewed before being published Name Please provide your name and last initial Submit Thanks for submitting a tip for review! Advertisement

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References

1. ↑ https://www.livescience.com/60060-humor-increases-attractiveness.html
2. ↑ https://www.mediacollege.com/journalism/interviews/open-ended-questions.html
3. ↑ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4816572/
4. ↑ https://www.psychologytoday.com/us/blog/evolution-of-the-self/201210/flirt-vs-tease-whats-the-difference
5. ↑ https://www.telegraph.co.uk/news/2017/08/14/using-emojis-makes-people-think-incompetent-research-finds/

About This Article

Co-authored by: Joshua Pompey Dating Coach This article was co-authored by Joshua Pompey. Joshua Pompey is a Relationship Expert and Founder of Next Evolution Matchmaking (NEM) based in New York City, NY. With over 15 years in the industry, Joshua helps his clients navigate online dating and has a success rate of over 99%. His work has been featured in CNBC, Good Morning America, Wired, and Refinery29 and he has been referred to as the best online dater in the world. This article has been viewed 4,111,639 times. How helpful is this? Co-authors: 122 Updated: June 5, 2025 Views: 4,111,639 Categories: Featured Articles | Texting | Flirting Article SummaryX

To flirt through text messages, start with a creative opening to get your crush’s attention, like a funny story about something that you saw during the day. Alternatively, open with a question that shows you pay attention to them, like asking your crush how their meeting went or if they’re ready for their mini-vacation. If you’re feeling bold, ask your crush if they want to catch a movie or come over to share a bottle of wine. When it’s time to end the exchange, leave on a good note. For example, text that you’re looking forward to chatting more or that you have to go because you have a project that needs your attention. To learn how to tease your crush while texting, keep reading! Did this summary help you?YesNo

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  Anonymous

  Jul 2, 2017

  "I like the tip to let the other person text you first, instead of sending the first message to start every..." more

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Yes No Advertisement Cookies make wikiHow better. By continuing to use our site, you agree to our cookie policy. Co-authored by: Joshua Pompey Dating Coach Click a star to vote Co-authors: 122 Updated: June 5, 2025 Views: 4,111,639

Anonymous

Jul 2, 2017

"I like the tip to let the other person text you first, instead of sending the first message to start every..." more

Dustin Goldston

Nov 2, 2017

"I really appreciated the help on how to keep my crush's attention. I really like wikiHow. It has solved so..." more

Amanda Jackson

Mar 20, 2016

"This really helps, thanks. Try making more emoticons is a good idea."

Anonymous

Jan 17, 2018

"Knowing when to stop was a good one. I need to work on that!"

Dee Da

May 13, 2021

"This was super helpful!" Share yours! More success stories Hide success stories

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