How to Attract a Guy Through Text: 15 Subtle, Effective Strategies for Meaningful Connection
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 Midnight Text That Changed Everything
One rainy Seattle evening, a client—let’s call her Claire—texted me in a panic: “HE RESPONDED TO MY STORY! What do I say now?!”
She’d been crushing on a guy from her spin class for weeks, and this was her first digital opening.
Together, we crafted a reply that felt playful, not desperate: “Glad someone noticed my questionable latte art skills 😉 How’s your week looking?”
Two days later, they had their first date.
As a dating coach for nearly 10 years, I’ve seen how texting can make or break modern connections.
It’s not about “rules” or mind games—it’s about authenticity, curiosity, and strategic warmth.
Let’s break down 15 actionable tips I’ve used to help clients (and myself!) navigate the messy, thrilling world of digital flirtation.
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1. Start with a “Soft Open” – No Pressure, All Curiosity
Forget “Hey” or “What’s up?” Begin with a shared moment:
- Reply to his Instagram story: “That hiking view 😍 Tell me the trail name before I kidnap your dog as my guide.”
- Reference an inside joke: “Saw a guy wearing socks with sandals today. You’d hate it. (Or… do you own a pair? 👀)”
Why it works: A client landed a second date by texting her match after a comedy show: “Still laughing at your ‘dad joke’ about the avocado. What’s your second-worst one?”
Pause here: What’s one thing you’ve noticed about him recently? Use it as a conversation starter.
2. Match His Energy (But Don’t Mirror His Laziness)
If he sends paragraphs, reciprocate with thoughtful replies. If he’s brief, keep it light but engaged:
- Him: “Long day at work.”
- You: “Ugh, solidarity. What’s your go-to stress snack? (Mine’s popcorn with way too much salt.)”
Avoid: Over-investing in low-effort texters.
A client realized her crush wasn’t serious when he only replied with “lol” to her heartfelt messages.
She moved on—and met her current partner two weeks later.
3. The 70/30 Rule: Let Him Lead… Sometimes
Initiate 30% of conversations early on to show interest without overwhelming him. For example:
- You: “Random Q: Pineapple on pizza—crime against humanity or underrated genius?”
- Him: “Crime! Fight me.”
- You: “Oh this is WAR. Meet me at Mario’s Pizza at 7. Bring your lawyer.”
Pro tip: One client alternated between playful questions and sharing snippets of her life (“Just adopted this plant—named it Steve. Pray for us.”), keeping the balance natural.
4. Use Open-Ended Questions Like a Pro
Ditch: “How was your day?”
Try:
- “What made you smile today?”
- “If you could teleport anywhere for dinner right now, where would you go?”
- “Confess: What’s a song you secretly love but would never play at a party?”
A grad student I coached asked a guy, “What’s the weirdest thing you believed as a kid?”
He wrote back a 500-word essay about his dinosaur phase.
They’ve been dating for eight months.
5. Compliment His Choices, Not Just His Looks
Generic: “You’re hot.”
Strategic:
- “Your playlist game is elite—who knew you were a closet Taylor Swift fan?”
- “How are you always wearing the perfect shade of blue? Teach me your ways.”
Why it works: A client bonded with her now-boyfriend over his book recommendations.
Her text: “Just finished the thriller you suggested. I’ll never trust a librarian again. What’s next?”
6. Embrace the “Pause” – Don’t Fear the Typing Bubbles
Wait 5–15 minutes before replying to non-urgent texts. Use the time to:
- Finish your coffee
- Text a friend
- Breathe
Caution: Don’t play “hard to get” for hours if that’s not your style. Authenticity > games.
7. Send Voice Notes to Stand Out
A 30-second voice memo can feel more personal:
- “Just saw the craziest golden retriever in a raincoat—wish you were here to witness this.”
- Hum a snippet of a song he mentioned.
Client success: A shy woman sent a voice note laughing about her burnt cookies.
He replied: “Your laugh is my new favorite sound.”
8. Use Humor Like a Warm Hug, Not a Punchline
Avoid: Overused memes or sarcasm that could misfire.
Try:
- “Confession: I just tried to make pancakes. They look like sad tortillas. Send help.”
- “If you were a kitchen appliance, you’d be a toaster—reliable and low-key essential.”
Pro insight: One client won over her introverted crush by riffing on his love of bad puns: “You’re ‘aww nuts’? More like ‘aww-some.’ (I’ll see myself out.)”
9. Double-Text with Purpose
If he doesn’t reply, wait 2–3 days, then send a non-needy follow-up:
- “Just found this meme and thought of our pizza debate 😂”
- “Random, but have you seen the new season of [shared interest show]? No spoilers!”
Key: If he still ghosts, let it go. As I remind clients: “You’re a priority, not an option.”
10. Create “Bookmark” Moments for Future Conversations
Plant seeds for later chats:
- “I’m trying that new Thai place tomorrow—any dish I MUST order?”
- “You’ll never guess what my nephew just asked me…” [Don’t reveal the punchline yet!]
A client used this to transition to a first date: “You never told me your Thai food order! Let’s go test your recommendations Friday.”
11. Use Time Zones to Your Advantage
Late-night texts can feel intimate but tread carefully:
- “Just heard our song from the concert. Still gives me chills.”
- “Can’t sleep. Tell me something weirdly fascinating.”
Note: A nurse I coached sent a 2 AM “Just finished my shift—your turn: best and worst pizza topping?” to a guy she knew worked nights. They’re now engaged.
12. When in Doubt, Bring It Back to Him
People love talking about themselves. Use the “You” Focus Method:
- “How’d that big presentation go? You seemed pumped about it.”
- “You mentioned hiking last week—any trails you’re dying to try?”
Client example: A teacher rekindled a fading connection by texting, “Remember how you helped me with my resume? I got the job! Drinks on me?”
13. Master the Art of the Graceful Exit
End conversations on a high note:
- “Heading to yoga—tell me about that podcast episode later!”
- “Need to crash, but this convo deserves a part two 👀”
Avoid: Dragging out chats until they fizzle. Leave him wanting more.
14. Screenshot & Save Inside Jokes
Create a folder for memorable exchanges. Later, reference them:
- “Three months since the Great Pancake Disaster. I’ve upgraded to waffles 😎”
- “Saw another sock/sandal guy today. Still team ‘nope’?”
Why it works: A client’s relationship deepened when she texted, “Happy 6-month anniversary of you judging my karaoke song!” with a screenshot of their first chat.
15. When You Meet IRL, Reference Your Texts
Bridge the digital-physical gap:
- “So… are those blue shirts in your closet or was that just for the ‘gram?” [Playful wink]
- “I need to hear that terrible pun in person.”
Pro move: One woman broke the touch barrier by saying, “You’re taller than I imagined from your gym selfies,” while gently adjusting his scarf.
Final Words from The Darling Code
Texting is just the appetizer—the real connection happens face-to-face.
Start today: Dig through your last chat, find one moment to reignite (“Hey, you never told me…!”), and hit send. You’ve got this.
With heart,
The Darling Code
P.S. Save your favorite tip to your phone’s notes app! Tonight’s challenge: Text someone a question that starts with “What’s the story behind…” 💬
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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.
