So, you finally matched with someone who actually looks promising—no blurry group photos, no suspiciously perfect AI-generated face, and no bio that just says “6’1” (because apparently, that’s a personality trait now). Now what? You’re staring at your screen, thumbs hovering, thinking: What the hell do I say? I get it. The pressure to craft the perfect first message can feel overwhelming. But don’t worry—I’ve got you. As a dating coach in Boston, I can give you some tips on how to start a conversation on a dating app and sound unique.
How to Start a Conversation on a Dating App Without Sounding Like Everyone Else
1. Avoid the “Hey” Trap (Please, I’m Begging You)
Look, “Hey” is not a conversation starter (it’s a sound). It’s the dating app equivalent of waving at someone from across the street and hoping they do all the work. If you’re going to send the first message, make it count. So how to start a conversation on a dating app without saying just "hey"?
A good opener does one of three things:
✅ Shows you actually read their profile.
✅ Makes them smile.
✅ Gives them something easy to respond to.
Tip from a dating expert:
Instead of “Hey,” try:
“I see you’re into rock climbing. Do you prefer indoor or are you one of those fearless people who scale cliffs with zero hesitation?”
“You mentioned loving ‘The Office.’ Important question: Who’s your favorite character and why is it Dwight?”
“Your dog is adorable. What’s their name, and can I be their new best friend?”
2. Compliments Are Great—If You Do Them Right
Telling someone they’re beautiful is nice, but it’s also what 500 other people have already said. Compliment something unique about them instead.
For example:
“You have the best taste in music. That 90s throwback playlist in your bio is top-tier.”
“That travel pic in your profile is amazing—where was that taken?”
“Your dog looks like they have major main character energy. What’s their name?”
People love talking about themselves, so give them a reason to (and it's a great option how to start a conversation on a dating app).
3. Use Humor (But Read the Room First)
Dating apps can feel repetitive, so a funny or unexpected message can be a great way to stand out. But here’s the thing: not everyone will vibe with sarcasm or dark humor right away. Start light.
For example:
“Okay, important question: Would you rather fight 100 duck-sized horses or one horse-sized duck?”
“So, if we were in a heist movie, what role would you play? Mastermind, getaway driver, or distraction?”
“Be honest—how many of your pictures were taken just for this dating app?”
4. Ask Open-Ended Questions (So They Have Something to Actually Say Back)
Yes-or-no questions are conversation killers. Instead of “Do you like to travel?” (which leads to “Yes” or “No” and then awkward silence), ask:
“If you could have dinner with any fictional character, who would it be and why?”
“What’s one random skill or weird talent you’re secretly really good at?”
“What’s a small moment in life that makes you ridiculously happy every time?”
This invites them to share more, making it easier to build a real connection.
5. Match Their Energy (Don’t Be Too Intense Too Fast!)
Ever had someone send you a paragraph-long introduction while you’re still deciding if you even like their face? Yeah, don’t be that person. Pay attention to their responses—if they’re replying with short answers, don’t overwhelm them. Match their pace.
For example:
If they’re using emojis and keeping it light, match their tone:
“You have great taste in movies! 🎬 What’s the last one you watched that totally blew your mind?”
If they’re giving longer, thoughtful responses, engage deeper:
“I love that you’re into psychology! What’s the most interesting thing you’ve learned about people?”
If they’re responding with one-word answers… maybe don’t over-invest. Some people just aren’t great texters, and that’s okay!
Know When to Move Things Off the App
Apps are great, but they’re just the starting point. The real goal? Taking the conversation off the app and into real life (or at least a video call if you’re long-distance).
If you’ve been chatting for a few days and there’s a good vibe, suggest something simple:
“I’m really enjoying this convo—want to grab a coffee this weekend and continue it in real life?”
“This has been fun—Want to switch this to texting so we don’t get lost in the app void?”
“You seem really fun—What’s your go-to drink? Let’s grab one sometime!”
The key is to keep it light and natural. Believe me, if they’re interested, they’ll be happy to move things forward. If not? No worries—on to the next!
Now You Know How to Start a Conversation on a Dating App
If dating apps feel frustrating, remember: the goal isn’t to be perfect. It’s to be interesting, genuine, and just a little bit different from the rest. The more you focus on fun, easygoing conversation, the better your results will be. If you know how to start a conversation on a dating app originally, you can get way more responses.
And if you’re still feeling stuck, please reach out to a dating coach! Whether you’re struggling with first messages, first dates, or finding real connection (ahem, knowing your love languages in relationships can help a lot), I’ve got you.
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Anna Morgan Coaching specializes in guiding men and women in breaking through emotional barriers and developing the mindset and skills needed for successful dating. Anna offers 1:1 dating coaching for men, dating coaching for women, relationship coaching, and empowering dating profile pictures for successful online dating. Book a free discovery call and learn how your dating life can be changed.
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