Let’s Be Honest…
You matched. You waited. You thought: “Should I say hi?”
And then… either nothing happened or someone hit you with a “Hey :)” — and the chat fizzled like warm champagne.
Here’s the truth: most dating app conversations die because they never come alive in the first place.
That’s where I come in.
What Actually Works (and What Doesn’t)
After 15+ years helping singles across Toronto and Canada navigate modern dating, I can tell you — the best openers are:
- Personal, not generic
- Warm, not interview-style
- Rooted in something real, not cheesy gimmicks
Here’s what to ditch immediately:
🚫 “Hey”
🚫 “How’s your day?”
🚫 “You’re cute”
🚫 “So what do you do for work?” (Not until they know you’re human)
Try This Instead: 3 Message Starters That Spark
1. Lead with a compliment that shows you read their profile
“You’ve been to Sicily five times?! That’s my dream trip. What keeps pulling you back there?”
Why it works: it’s specific, flattering, and shows effort. That’s dating gold.
2. Ask a light, engaging question
“Okay, big question — pancakes or waffles?”
“If I had 2 tickets to a surprise show tonight, what genre would you hope it is?”
Why it works: It’s fun, non-threatening, and gives them room to show personality.
3. Share a tiny story or fun fact about yourself first
“I spent last Sunday hiking and then fell asleep in my car in the trail parking lot. I blame the sun. And carbs. How about you — what’s your ideal Sunday?”
Why it works: vulnerability + humour = connection.
The Secret Sauce? Don’t Be Afraid to Show You
We’ve been conditioned to think “cool and casual” wins. But real relationships aren’t built from lukewarm conversations.
If you’re looking for a deeper connection, your energy needs to say that — from the first message on.
And yes, this still works even if you’re a little awkward, shy, or out of practice.
Want Better Matches AND Better Chats?
If you’re tired of matching with the wrong people or never getting replies, it might not be you — it might just be your strategy.
That’s where I help.
✅ Online dating profile makeovers
✅ Message coaching (what to say, when, how)
✅ Personalized dating coaching that actually gets you dates that feel good
→ Explore online dating support
→ Book a free 20-minute consult with Rebecca
About Rebecca
I’m Rebecca Cooper Traynor, founder of Match Me Canada. I’ve helped thousands of singles across Canada find meaningful relationships — not through gimmicks, but by getting real about who they are and what they want.
I blend matchmaking with dating coaching, online profile support, and truth-telling with love. If you’re ready to feel more confident in your dating life — I’m here to help.
Additional Resources
Want to dive deeper into real-world dating trends and conversations?
In a Nutshell
Starting a dating app conversation that leads somewhere isn’t about clever lines — it’s about warmth, effort, and clarity. If you’re ready to start chatting like someone who’s ready for real love, Match Me Canada can help you do it.
