The Ultimate Guide to Flirting Over Text (Without Being Cringey)

Let’s be honest—sometimes, texting someone you like can be harder than it should. You are very careful not to sound boring, reply too fast, or come too strong so that things don’t get awkward. The way out, however, is to learn how to flirt over text like a pro.

This guide will show you how to win your crush over via texts—from starting the conversation to building chemistry and confidently asking them out. It’s beyond memorizing a list of pickup lines.

The Flirting Foundation: 3 Rules Before You Even Type

Rule #1: Confidence is Magnetic

When you’re confident, it shows in how you type and people can see it. You have to be comfortable while texting and enjoy the conversation. Project a fun, confident version of yourself. This is not to say you should be cocky or pretend to be who you are not.

Rule 2#: It’s a Game of Tennis

How not to be a dry texter means that the conversation must be back-and-forth. If they send a sentence, don’t reply with paragraphs, and vice-versa. When they ask a question, answer and then send a question back. You have to keep the rhythm—just let the conversation flow instead of forcing it.

Rule #3: Your Goal is to Make Them Smile

Every text doesn’t have to be super-clever or deep. The goal is to create a small, positive emotional reaction that will make them laugh and remember you always. How you know you’re doing well is when they say words like “that was cute” or reply with laughing emojis.

The Opener: How to Start a Flirty Conversation (and not with “Hey”)

How to start a flirty conversation is often the hardest part. Don’t start with words like “Hey,” “Hi,’ or “Hello” if you want to be unique and have their full attention.

Here are better ways to start:

1. The Observation: Mention something you noticed about them. It could be how attractive they look the last time you saw them, how they dress, how well they speak, etc. You can even comment about their social media. For example: “Just saw your story… You really went to that place without inviting me?” This feels natural and gives them an easy way to text back.
2. The Callback: How to text your crush can start from referencing a previous conversation. For example: “I am still thinking of that hilarious story you told earlier… still laughing about it😂.” This works because it picks up from where you left off instead of starting from nothing.
3. The Playful Question: Ask a fun, low-pressure question in a way that makes replying feel easy and enjoyable. For example: “What’s your most controversial food opinion? I promise not to judge too much.” This makes them not only answer but explain why their answer is what it is. It gives you an insight into their personality, which is helpful for follow-up messages.

5 Key Ingredients of a Flirty Text

Flirty text messages that work are not complicated. They just have a few key ingredients, which are:

1. The Specific Compliment

When offering a compliment or saying anything that will make them smile, be specific. There’s a huge difference between a generic “you’re cute” and one that’s more explanatory & specific.

Compare these:

• “You are smart.” ❌
• “The way you explained that topic today made it so easy to understand. I was impressed.”✅

Or

• “Nice outfit.❌
• “That jacket you wore today really suits you. What a great taste!”✅

Playful Teasing

Teasing your crush adds spice to the conversation, but only when done correctly. Your aim here is to be playful, not mean or disrespectful.

The formula: Light tease + emoji (to show you’re kidding)

Example:

• “Wait… you actually like pineapple on pizza? I don’t know if I can trust you anymore 😉”
• “I can’t believe you’re a fan of Jazz. Maybe we shouldn’t be friends anymore😁😄”

Engaging Questions

Move beyond asking common questions like, “how was your day?” Be flirtatious with your questions so that you will keep them smiling and wanting to talk to you.

Some flirty questions to ask are:

• “If we ditched work tomorrow, where would you take me?”
• “What’s something small that instantly puts you in a good mood?”

Using Emojis and GIFs (The Right Way)

Sometimes, texts lack tone. You need flirty emoji combos and GIFs to better communicate what you mean or your facial expression. However, they shouldn’t be overused. One or two per message is usually enough.

Here are some notable ones and their meaning:

• 😏 = playful confidence
• 😉 = teasing / joking
• 🔥 = attraction or hype
• 😄= smiling or kidding
• 😂 = warmth and laughter

Inside Jokes

How to flirt over text is easier when you have an inside joke. The moment you do, you’re no longer just “someone,” you’re their person. The joke can be something simple, maybe a nickname, a shared moment, or a silly misunderstanding you both laughed about. Bring it back occasionally when texting to be hilarious.

Example:

• “This reminds me of our ‘worst movie ever’ debate 😉”
• “That was how you stole my note in class 😉”

The Zero-Risk “Secret Admirer” First Move

Are you feeling too shy to even start? What if you could gauge their interest with zero risk of rejection? That’s where “anonymous first move” comes in. It helps you in asking a girl/guy out over text without revealing your name. Think of it as flirting behind the curtain.

This is how it works: You send a thoughtful, anonymous compliment. Nothing creepy, nothing intense. Just something good enough to make them curious. Their reaction to the idea of a secret admirer will tell you everything you need to know about their openness to romance.

You can follow this guide:

1. Craft the perfect anonymous compliment. Keep it short and genuine.

For example:

• “Someone in your class thinks you have an amazing smile.”
• “Just so you know, someone at work really admires your energy.”

2. Send it and wait. Use anonsms.com to keep your identity a secret. Just send the message; don’t follow up.
3. Observe how they react after reading your message. Do they mention it? Joke about it? Look excited or curious? Their reaction will inform you on how to follow up.

For a complete playbook on this strategy, check out our guide on how to break the ice with your crush anonymously and how to test the waters before making a move.

Flirty Text Scenarios You Can Steal

Below are some flirty text messages you can simply copy-and-paste to the person you like.

1. The “Good Morning” Text That Isn’t Boring

Here are some good morning flirty texts for your crush:

• “Good morning. Hope today treats you nicely! Try not to miss me too much 😉”
• “Rise and shine. Hope you have a great day! I would be thinking of you 🙂”

2. Responding to Their Story

Here are some subtle flirting examples in response to their posts on social media:

• If they post FOOD: “That looks illegal. Where is my invite?”
• If they post a SELFIE: “You really woke up and chose to look this good?”

3. The “Thinking of You” Text

Here are some ‘flirting without being creepy’ examples to show you’re thinking of them:

• “I just passed that coffee shop we talked about and it made me smile 😃 ”
• “This song came on and instantly reminded me of you.”

4. How to Ask Them Out

Here are some flirting tips script you can use to ask them out:

• “I am having way too much fun talking to you over text. We should do this in person. Are you free for a drink on Thursday?”
• I think we would get along even better offline. Dinner next week?”

Flirting “Don’ts”: 5 Mistakes That Will Kill the Vibe Instantly

Below are major things you should never do when asking a girl/guy out over text:

1. The One-Word Answer

Don’t reply with single, abrupt words like “k,” “lol,” or “nice.” They are vibe killers and would shut down the conversation fast.

2. The 24/7 Texter

You should not constantly message them—it can feel overwhelming. Let the conversation breathe. Give them space to anticipate hearing from you.

3. Unsolicited Dirty Talk

Flirting comes before anything sexual. Don’t sexualize conversations until you’ve gotten closer. Doing so too early can get you ignored or blocked.

4. Complaining or Being Negative

Flirty text messages are meant to be sweet, playful, and positive. They are not the place for venting or negative thoughts.

5. The Dreaded “Double Text” (When Not to Do It)

Double texting is only ideal when you’re continuing a conversation, not when they are yet to reply to the very first question. Don’t send texts like, “Did I say something wrong?” or “?? because they haven’t replied.

Conclusion

How to flirt over text is a skill that’s learnt, and like any skill, it gets better with practice. When you focus on being confident, playful, and respectful, your messages feel natural instead of forced. You don’t need perfect words—just the right energy.

Now that you’ve gotten the flirting tips, you need to take the next move. Pick one message from this guide, open your phone, and send the text to make your crush smile.