50 Texting Tips That Actually Lead to Dates (Tested by Real Guys)

Megan

50 Texting Tips to Turn Your Phone Into a Date-Generating Machine

Gentlemen, let’s face it: in the digital age, your thumbs can make or break your love life. Whether you’re swiping right on Tinder or sliding into DMs, mastering the art of texting is crucial. But fear not—we’ve gathered intel from guys who’ve been in the trenches and come out victorious. Here are 50 texting tips that’ll turn your phone into a date-generating machine.

The Opening Salvo

  • Ditch the “Hey.” It’s boring, overused, and screams low effort.

  • Reference her profile: “I see you’re into rock climbing. Ever scaled El Capitan?”

  • Use her name: “So, Sarah, what’s the story behind that tattoo?”

  • Use emojis sparingly. One or two adds flavor—don’t go overboard.

  • Ask an open-ended question: “What’s the most spontaneous thing you’ve done lately?”

Keeping the Conversation Rolling

  • Follow the 2:1 rule: For every question you ask, share two pieces of info about yourself.

  • Be genuinely curious. Ask thoughtful follow-ups.

  • Use callbacks: “Remember that weird bird we saw? I just saw its cousin steal my lunch.”

  • Avoid one-word responses. They kill conversations.

  • Don’t double text. Desperation isn’t sexy.

Humor: Your Secret Weapon

  • Self-deprecating humor shows confidence. “I tried yoga once. Instructor asked me to leave for the safety of others.”

  • Use puns sparingly. A good one charms; a bad one bombs.

  • Memes work wonders when timed right.

  • Avoid sarcasm—it doesn’t translate well in text.

  • Know your audience. What’s funny to you might not be to her.

Flirting Without Being Creepy

  • Compliment her mind: “Your take on climate change is fascinating. Coffee and more of that?”

  • Use innuendo sparingly. A little goes far.

  • Playful challenges: “I bet I can guess your favorite movie in three tries.”

  • Create inside jokes for a bond.

  • Skip generic pickup lines unless you’re using them ironically.

The Art of Timing

  • Don’t play games. Waiting three days is childish.

  • Match her pace. If she replies in hours, don’t text every five minutes.

  • Avoid late-night texts unless you’re already there with her.

  • Know when to step back. Mystery keeps it exciting.

  • Strike while it’s hot. If the convo flows, suggest meeting.

Grammar and Etiquette

  • Proofread. Sloppy grammar kills attraction.

  • Avoid ALL CAPS unless you’re actually shouting.

  • Punctuation matters: “Let’s eat, Grandma” vs “Let’s eat Grandma.”

  • Abbreviations in moderation: “LOL” works, “ROFLMAO” doesn’t.

  • Never send unsolicited pics. Ever.

Building Attraction

  • Share your passions. Enthusiasm is magnetic.

  • Keep some mystery. Don’t tell your life story in one chat.

  • Use descriptive language: “There’s a hidden beach where sunsets set the ocean on fire.”

  • Flirt with action: “If you were here, I’d challenge you to a dance-off right now.”

  • Build anticipation: “There’s this hole-in-the-wall spot you’ve got to try. I’ll take you.”

The Path to a Date

  • Be direct: “I’m enjoying this. Want to grab drinks?”

  • Offer specific plans: “Jazz bar downtown, Thursday at 8?”

  • Have a backup if she’s busy.

  • Use time constraints: “I’m free for an hour tomorrow afternoon—coffee?”

  • Be flexible. If she suggests something, roll with it.

Red Flags to Avoid

  • Don’t overshare. Childhood trauma isn’t first-date material.

  • Avoid ex talk. Leave the past in the past.

  • Don’t be pushy. Silence is an answer.

  • No guilt trips: “I guess you’re too busy for me” reeks of manipulation.

  • Keep it PG-13 unless she takes it further.

The Home Stretch

  • Confirm plans: “Looking forward to tomorrow at 7!”

  • Keep it light before the date. Save deep convos for in-person.

  • End on a high note: “Sweet dreams. More banter tomorrow.”

  • Be yourself. Authenticity is always the trump card.

Texting is just the prelude—the real magic happens face-to-face. These 50 tips will get you from her inbox to an actual date, but remember: every woman is different. Stay adaptable, stay confident, and keep your wit sharp.

Now go forth and text, you smooth operators. May your thumbs be swift, your grammar flawless, and your dates unforgettable.