Flirty Texting 101: How to Make Him Think About You Constantly
The experiences shared in this article are based on real emotional journeys, but all personal details are anonymized and used with the explicit written permission of the clients. Any resemblance to actual persons, living or dead, is purely coincidental. We are committed to treating all client stories with the utmost confidentiality and respect.
The Text That Changed Everything
One rainy afternoon, a client named Freya slid her phone across my desk with trembling hands. “He hasn’t replied in three days,” she whispered.
The screen showed a painfully overthought paragraph ending with “Hope you’re okay?”—a classic “safe” message that buried her spark under layers of worry.
Over lattes, we workshopped a simple replacement: “Saw this sunset and instantly wished you were here to steal my fries while I take photos. Miss your terrible taste in ketchup brands.” The reply came in 12 minutes.
That’s the magic of flirty texting done right: it’s not about manipulation, but about inviting someone into the vibrant, unapologetic version of you.
After coaching hundreds of women through dating apps, long-distance limbo, and post-first-date jitters, I’ve learned that great texting is less about rules and more about intentional playfulness.
Let’s dive in.
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1. Start With Curiosity, Not Interrogation
Instead of “How was your day?” (the text equivalent of beige wallpaper), try:
“Bet you just invented a new coffee order today—spill the details, mad scientist.”
Why it works: You’re inviting him to share while showcasing your humor.
A client once used this line on a barista she’d been eyeing; he sent back a photo of his lavender-infused espresso concoction with “Taste-testing tomorrow? Lab partner needed.”
Your Homework: Next time you’re tempted to ask a generic question, add a playful assumption.
Warm Pause: Which of your unique interests could become a curiosity-starter?
2. Leave Space for His Imagination
The best texts are 70% complete—like a movie trailer hinting at the plot.
After a great date, avoid:
“Last night was amazing! We should do it again soon :)”
Try instead:
“Still recovering from your shockingly good karaoke rendition of ‘Livin’ on a Prayer.’ Who knew accountants had pipes?”
Case Study: A client in a fledgling situationship used this strategy after a hiking date, texting: “Found a pinecone that looks exactly like your ‘I’m lost but pretending I’m not’ face. Exhibit A attached.” He proposed their next adventure within hours.
Pro Tip: Highlight specific, quirky memories—they linger in his mind longer.
3. Match His Energy (Without Losing Yours)
If he sends a novel-length text about his rock-climbing trip, respond with equal enthusiasm.
If he’s terse but consistent (e.g., “Crazy day. Talk tomorrow?”), mirror that rhythm without overcompensating.
But: Never dim your spark to match his.
During a coaching session, Sarah realized she’d been editing her witty personality into “chill girl” one-word replies to avoid “scaring off” a lawyer she liked. We workshopped a middle ground: “Your ‘brief’ texts are longer than my grocery lists. Impressive.”
He laughed, apologized, and started sending voice notes.
Your Move: If he’s low-effort for weeks, prioritize men who match your communication values.
4. Use the “Tomato Timer” Technique
Set a 25-minute timer before replying to his really good texts. Why?
- Prevents overthinking (“Was that emoji too much?”)
- Lets anticipation build (for both of you)
- Gives you time to craft something intentional
Real Talk: I once waited 40 minutes to respond to a guy’s “You’d hate this art gallery—too many triangles” with “Triangles are just squares with commitment issues. Be there in 20.” We dated for eight months.
Caution: Don’t game-play—if you’re free and excited, reply! This is for stressful overthinking moments.
5. The “Three-Beat Rule” for Flirty Banter
Think of texting like jazz: call, response, riff.
Example:
Him: “Just survived a 4-hour Zoom meeting. Send caffeine.”
You: “Plot twist: I’m replacing your coffee with decaf. Welcome to chaos mode.” (Beat 1: Playful challenge)
Him: “You monster. I’ll retaliate with endless cat videos.”
You: “Joke’s on you—I’ve trained my cat to swat phones. Your move.” (Beat 2: Escalate the bit)
Him: “…Fine. Truce? Dinner tonight?”
Key: End the volley on a high note (like his invite above). Don’t drag the bit into a 12-text saga.
6. When in Doubt, Activate the “Shared Universe”
Build an inside joke world only you two inhabit.
My Story: A guy once teased me for mispronouncing “quinoa” as “kwin-oh-ah!” at a farmers’ market.
Later, I texted: “Eating my shame-quinoa salad. You’ll be pleased to know I’ve hired a pronunciation coach.”
For months, we referenced “The Great Quinoa Debacle”—it became our thing.
Your Turn: Turn a mundane moment (e.g., him spilling coffee) into your shared lore: “RIP to the white shirt you loved more than me. Funeral services at 8?”
7. The Art of the Strategic Vulnerability
Flirting thrives on lighthearted authenticity. Try:
“Confession: I just rewatched Pride and Prejudice for the 14th time. Judge away.”
Not: “I’m scared you’ll think I’m boring.”
Client Win: Lauren texted a guy she’d been ghosted by before: “Hate that I’m texting you again, but your dog’s Instagram reel got me. How’s Captain Fluffington?” He replied: “He misses his favorite chew toy (you). Coffee?”
Boundary Note: Share vulnerabilities that feel safe, not soul-baring.
8. When He’s Distant: The “Soft Reset” Text
If he’s been MIA, avoid:
“Are you mad at me??”
Try:
“Haven’t heard your hot take on pineapple pizza in a while. Everything cool?”
Why Better: It’s curious, not accusatory. Gives him space to explain without pressure.
Case Study: After a client’s date vanished post-intimate night, she sent: “Hey, I had fun last week—but I’m a mind reader in training, not a pro. Let me know where you’re at?” He apologized, explaining a family crisis. They reconnected.
9. Always Text From a Full Cup
The golden rule? Never seek validation through texts.
A client once asked, “How do I make him text first?” My response: “How can you make your day so fulfilling that his texts are the icing, not the cake?”
My Ritual: Before sending a nerve-wracking text, I ask: “Does this feel true to me, or am I performing?”
Final Words from The Darling Code
Flirty texting isn’t about tricks—it’s about choosing men who celebrate the real you.
Start tonight: Pick one tip above and text that guy (or match) you’ve been overthinking about.
Not sure? Re-read #9. Your energy is sacred; invest it wisely.
With heart,
The Darling Code
P.S. Save this to your Pinterest “Dating Wins” board! Your tiny action today: Send one text that feels 100% you—no edits. Even if it’s just: “This taco truck made me think you’d steal my guac again. The audacity.”
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ABOUT THE AUTHOR
Vivienne, Relationship Coach & Self Love Coach
Vivienne is a Relationship Coach and Self-Love Coach who believes the key to great relationships starts with YOU. She helps individuals and couples build confidence, set healthy boundaries, and create connections that truly honor who they are.
