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Flirting over Instagram text chatting can be a challenge, especially for shy guys or those looking to figure out if their game is really as strong as they thought it was. If you’re one of the many men out there who suck at the flirting game, to be honest, this guide is for you. By the time they’re done, they’re either completely turning you off with their words, actions or inactions, or basically they just have no game and so they walk away feeling defeated mostly. If that’s you, and you know yourself, you don’t need me to tell you. Thank you so much for joining this particular article, I’m gonna make it worth your while. Here are four practical tips, straight from dating coach Anshu, to help you master texting flirtation, complete with examples to spark your next conversation.

Why Flirting Over Text Matters

Texting is often the first step in building a connection in today’s dating world. There are lots of men out there who struggle with flirting over text because they go overboard or miss the mark. The key is to keep it short and sweet, stay positive, be complimentary, and ask playful questions. Let’s dive into the tips to make your texts stand out.

4 Tips to Flirt Over Text Like a Pro

1. Keep It Short and Sweet

Now in my opinion, the first tip is to keep it short and sweet, very important, short and sweet. There are a lot of guys who just go out there and it’s like okay, I’ve seen this girl, I’m really feeling her, let me just go right ahead and tell her everything that’s on my mind, how she made me feel, how your heart was just out of your chest when you saw her and that kind of thing. That might actually be a cool thing to do but alternatively don’t forget that depending on how you do it it might come across as imposing downright disruptive or maybe even unwelcome, depending on once again who you’re talking to and the circumstances surrounding where she currently is at. So if you want to know how to flirt with a woman over insta text, my first tip is to keep it short and simple. Short and simple.

There is an acronym that says ‘KISS’ “Keep It Simple Stupid”. What that simply means is, when you’re sending a text to a woman, amongst other things, go straight to the point, don’t blab, don’t brag, don’t stretch the conversation unnecessarily. If you ask me you might even want to make a deliberate effort to use open-ended questions that will motivate her to talk some more. Because if you ask questions like (‘Whats Up’) and she says (‘nothing’) What will you say after that? Okay maybe (‘Having a good day’) then she says (‘YES’) Are you going to be doing that little dance with your thumbs or twiddling with your thumbs to try and figure out what to type next.

• Why it works: Open-ended questions always allow the person who’s being asked the question to elaborate, keeping the conversation flowing naturally.
• Examples:
• Missing that face. Send me a picture
• So, I had a crazy dream about you…
• What are you doing this weekend besides being with me?

What do you think? I think you just scored a hundred, personally.

2. Stay Positive and Light-Hearted

Stay positive, stay positive and I know it can be hard, especially if maybe the lady who you’re engaging with is not forthcoming, but it’s always good to keep a positive tone. Typically flirting is supposed to be friendly, light-hearted, not taken too seriously, okay, so if you want to flirt with a woman, you need to keep that whole positive energy and let that shine through the messages that you send. Remember, if you’re going for a flirty tone, you always want to keep it light and avoid talking about heavy, intense stuff because then that makes the conversation awkward and especially if she’s not really too keen on engaging with you then you lose out from the get-go.

• Why it works: Positivity is attractive and helps her associate you with good feelings.
• Examples:
• Got great news and guess what? You’re the only one I wanna tell.
• Thinking about the story you told me. When do I get to hear more
• The movie you mentioned! I’m hooked. How do you know me so well?

What do you think, this might get you somewhere, like that whole thing about her being the first person you wanted to tell or her being the first person you thought about, kind of tells her that hey, I really, really like you and I actually have you in mind most of the time and I’d like to get to know you a little bit, if you’re open for it. Messages like that will get you far.

3. Be Complementary

Be complementary, be complementary. As they say, flattery will get you anywhere however, I do believe that the more sincere a comment or a compliment is, the more it will be taken to heart and seen for what it truly is all right, so don’t go about you know saying stuff like, I think you have an amazing and you mentioned a body part knowing very well that the woman is probably even insecure about that, better yet if you’re not sure then don’t even go there trying to mention body parts or trying to compliment her on any part of her body, because it gets tricky when it comes to women. The way men see women is completely different from how we see ourselves and so the thing that may be really getting you going, might be that thing that really makes her feel down because she thinks maybe she has too little of, a whole lot more of, etc.

So learn to be complimentary, let her know if there are certain things about her that you like and if you ask me steer clear of compliments that necessarily involve her body and more about the way she thinks her brain her achievements and that kind of thing. A lot of women like to think and especially women who aren’t and you can tell usually the kind of woman that you’re dealing with if she’s a woman who isn’t big on looks necessarily and is not the kind who will go on social media to take pictures and show her behind because that seems to be the only leverage she has then she would appreciate compliments via text in a manner that complements her thought processes more than anything else.

• Why it works: Sincere compliments build trust and show you’re paying attention to who she is.
• Examples:
• Your energy is so contagious—how do you stay so upbeat?
• That idea you shared the other day was so smart. Tell me more about how you think.
• Your laugh is honestly the best part of my day.

4. Ask Playful Questions

Let’s move on to our final tip for today’s article, it’s simply to ask a playful question. So once again flirting is supposed to be light-hearted, playful, not too serious, not too intense, like I said in a previous conversation. So send a playful message, a playful text.

• Why it works: Playful questions spark curiosity and invite her to join in the banter, creating a dynamic conversation.
• Examples:
• Guess the emoji I put next to your name on my phone (she may say Which one) and then you can respond (I’d like to show you in person)
• How can I concentrate when all I do is think about you? (she may answer Wanna hang this weekend?)
• What’s one thing I have to know about you before we hang out this weekend?

And you might end up getting somewhere.

Bonus Tips for Flirting Over Text

If you’ve already met up in person at least once or you’ve been conversing quite a lot, then you can use flirty texts as an opportunity to solidify an inside joke. Now the thing about that is inside jokes, you know sort of elicit a feeling of intimacy, familiarity and they usually go down very well and that is only if you do indeed have some kind of inside joke, a joke that’s shared between just the two of you, that if you made a comment in public she’d be the only one who would get it, right inside joke okay.

In your text messaging, you can feel free to add an emoji or two with your flirty text for a little emotional flavor, but don’t go overboard. So what you say with your words is what counts emojis are only supposed to add a little bit of flavor, flavor to your messages so don’t go overboard don’t overuse them such that she needs to like ask other friends or what does this mean or what does that mean, of course depending on the age of the woman some of them, some women care others really don’t, so use emojis but use them sparingly and let it help send your message home.

My last hint or tip I’ll give you, is to keep in mind that whilst flirting is great and it can be interesting over text, in my opinion the best way to flirt is face to face, it always helps when the person is right in front of you, your expression send a message, your tone of voice as a message, a lot of things that are usually lost in text messaging you can do in person to really drive your message home.

Common Mistakes to Avoid

• Don’t send long paragraphs or multiple texts before she responds.
• Avoid heavy, intense stuff that makes the conversation awkward.
• Skip generic questions like “Whats Up” that lead to dead-end replies.
• Pay attention to her responses—if she’s not forthcoming, give her space.

Why These Tips Work

So that’s it for today how to flirt over texts. These strategies work because they keep things light-hearted, engaging, and authentic, whether you’re just starting to text or building on an existing connection. Drop a comment below with your favorite texting example or share how these tips worked for you! If you like this article, don’t forget to subscribe for more dating advice to level up your game.

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FAQs About Flirting Over Text

1. How do I start a flirty text conversation?

You could say something like, hey, I had a really terrible day, I had a flat tire or something really bad happened either at school or at work and I’m kind of hoping that you had a better day than I did. Now, not only have you told her that you want to know whether her day is actually going well, you’ve also started by telling her how your day went, so most likely her answer would be more engaging as opposed to a simple yes or no answer, closed answers.

2. What if she doesn’t respond to my flirty texts?

If maybe the lady who you’re engaging with is not forthcoming, stay positive and I know it can be hard. Don’t send multiple texts right away. If she’s not really too keen on engaging with you, give her space and try again later or consider flirting in person to build a stronger connection.

3. How often should I wait to text her back when flirting?

There’s no strict rule, but respond when it feels natural. If she’s replying quickly, keep up the pace to avoid twiddling with your thumbs to try and figure out what to type next. Matching her energy keeps the conversation flowing.

4. Can I flirt over text if we’ve never met in person?

Yes, but keep it short and simple. Try something like, “Just curious—what’s something I’d notice about you if we met right now? 😊” This is playful and low-pressure, inviting her to share without being imposing downright disruptive.

5. What are some flirty texts to send at night?

Try a text like, “Can’t sleep… wondering what you’re dreaming about tonight 😏” or “Just wanted to say goodnight—you’re kinda on my mind.” These keep it light and hint at interest without being too intense.