Online Dating Texting Tips: From First Message to First Date

Follow these online dating texting tips to go from first message to first date with confidence and success!

—

Let’s talk about that part of online dating no one trains us for: the texting. You match, you smile, maybe you even do a little happy dance… and then the real question hits: What do I say now?

You want to be charming, confident, interested—but not desperate. You want to move things forward—but not force anything. And most of all, you don’t want to end up in a two-week text-a-thon that goes absolutely nowhere.

Here’s how to navigate the texting stage like a high-value, confident person who knows what they want—and knows they’re worth it.

Online Dating Texting Tips: How to Go from First Message to First Date with Confidence

1. Be Intriguing, Not Exhaustive

Imagine this: You’ve just started watching a great Netflix show, and someone spoils the ending. That’s what it feels like when you pour out your entire life story in one text.

Instead, give teasers, not chapters. Think of texting as a trailer, not the whole movie. Drop a fun detail, tell a quick story, share a quirky fact about yourself—but leave room for curiosity. The goal isn’t to prove you’re interesting, it’s to spark interest.

“I once spent a weekend learning salsa in Havana. I wasn’t great, but I smiled the whole time.”

See what we did there? Light, a little mysterious, and opens a door for connection.

2. Don’t Just Chat—Make Plans

Look, texting should be a bridge to something real—not a virtual pen-pal situation. If the vibe is good, go somewhere with it. Ask about their week, their go-to local spots, their favorite way to spend a Saturday. Then suggest something specific.

“You mentioned you love live music. There’s a jazz night at The Virgil this weekend—want to check it out together?”

This shows confidence, initiative, and that you’re actually looking to date, not just pass time on an app.

3. Keep It Light and Playful

Early dating should feel fun, not like a therapy session. Avoid diving into intense personal topics over text. Instead, lean into humor, gentle teasing, and flirtation that makes them smile when their phone buzzes.

“If you had to delete all but three apps on your phone, which would survive—and why is one of them snacks-related?”

It’s cheeky, it’s open-ended, and it creates space for personality.

4. Ask Open-Ended Questions

If your texts sound like interview questions, you’re doing it wrong. “How was your day?” is nice.

“What’s something that made you laugh today?” is better.

Open-ended questions give the other person a chance to show who they are, not just what they did. And let’s be honest: better conversations lead to better chemistry.

5. Read the Signals

Let’s not ignore the elephant in the chat: some people just aren’t that into it.

If you’re getting one-word replies, delayed answers, or constant “let’s raincheck” vibes, move on. Attraction is mutual or it’s just a daydream. Protect your energy. When someone’s excited about you, you’ll feel it.

6. Compliment with Intent

A sincere compliment goes a long way—but only if it’s real. Instead of generic praise (“You’re hot”), try something specific and personal.

“You have this confident, grounded energy—I like it.”

Boom. Thoughtful. Memorable. Not something they’ve heard a hundred times today.

7. Use Their Profile to Your Advantage

They posted that hiking photo or sushi obsession for a reason—so use it! Not in a creepy way, but in a I’ve actually paid attention to you kind of way.

“Okay, I have to ask… what mountain were you on in that pic? Looked amazing.”

This shows effort, interest, and awareness. Three things that separate you from the sea of lazy texters.

You’re Not Here to Impress—You’re Here to Connect

Texting isn’t a performance. It’s a preview of what it feels like to be around you. So show up as you. Relax. Lead with curiosity, confidence, and joy—and remember: the goal isn’t a perfect conversation.

It’s a real connection that leads to a real date—with someone who’s just as excited about you as you are about them.

Be prepared for every first date! Enter your first name and email to get my FREE First Date Strategy Checklist.

---

If you’re feeling stuck in dating and relationships and would like to finally find your person, sign up for a complimentary 45-minute love breakthrough session with Sandy https://lastfirstdate.com/application

Join Your Last First Date on Facebook https://facebook.com/groups/yourlastfirstdate

Get Sandy’s books, Becoming a Woman of Value; How to Thrive in Life and Love and Choice Points in Dating; Empowering Women to Make Healthier Decisions in Love and Love at Last: True Stories of Falling in Love Later in Life

from Last First Date https://ift.tt/gJPMRIm