So you got a match on Tinder (or Bumble/Hinge).

You check out her profile, looking for something you can use as a first message. You’ve heard clever opening messages for dating apps can get you replies, but how do you actually start a conversation that guarantees her response?

You may think it’s simple enough:

Make an observation, ask a question, start a conversation.

But reality never plays out that way. She either doesn’t reply… or sends back a one-word “hi.” And suddenly, your thoughtful message feels like it didn’t matter at all.

Truth is, thoughtful messages aren’t going to guarantee you a reply. Here’s why:

1. It’s too serious.

Most women aren’t looking to dive into a thoughtful conversation with someone they don’t know yet. It feels like too much, too soon. That kind of emotional energy is for someone whose company she already enjoys.

2. It’s time and energy she cannot spare.

If she replied thoughtfully to every guy who tried… she’d be texting all day.

Don’t get me wrong. Thoughtful messages are nice. They do stand out from the typical “hey” or “wyd”.

But if your goal is to get her to reply, then…

The smarter way is to play.

Humans are wired to respond to playfulness. So when your opener has a hint of fun, you’re giving her something she actually wants to engage with.

Over the years, I’ve tested hundreds of opening messages on dating apps. These 5 techniques consistently stand out as the most successful in getting responses.

They’re easy to use and the conversation gets on a good momentum right away. They also allow you to spark interest, in a space where attention is short and impressions are instant.

Let’s break them down:

(All the opener examples below have received replies. Ask for the screenshots if you wish to see them.)

1. Playful Framing + Personalization

This technique is all about framing your interaction with her in a playful way.

Example 1

“[name], we should make it our mission to discover Singapore’s best cozy cafes. And who knows, we might find one that could be our favourite haunt 😉”

• Why it works:

She mentioned in her bio that she “prefers to chill in a cozy cafe” and this opener takes that little detail and turns it into an invitation, for a potentially great time.

Example 2

“[name], I have to let you know in advance. Getting to know me means you’ll be entering into my relationship with cats…”

• Why it works:

Her photos suggest she’s a cat lover. I added a bit of a twist into that to make the opener unique and tell her I am the same without being direct.

2. Imaginative Scenario Creation

Forget interviews. Women don’t come to dating apps for job applications. They come for a vibe. This technique invites her into a tiny story or playful fantasy, while building togetherness with her. It sparks her imagination and allows her to envision what it looks like hanging out with you.

Example 1

“Pocket sized merely means we might be able to sneak you onto a plane and travel for free!”

• Why it works:

Her bio said she was “pocket sized”. This creates a playful imaginative scenario that invites her into a shared fantasy of traveling together and it hints at how fun you might be.

Example 2

“Oh no. We matched after Valentine’s Day. Is it too late? 😂 Or are we gonna prepare for next year’s one…”

• Why it works:

Missed an opportunity with Valentine’s Day? Not an issue. This opener adds a bit of humour while generating a fun mental image of us celebrating the next Valentine’s Day together.

3. Subtle Teasing with Confidence

This is where most guys are either too soft or too aggressive. The sweet spot? A line that lightly challenges her… with charm. It shows you’re not a pushover, and you’re confident enough to playfully start with a tease.

Example 1

“Reformed, but seeking partner in crime. Sounds like a part of you still loves trouble…”

• Why it works:

Her bio: “Reformed recalcitrant seeks peer, playmate and partner in crime”. This opener reframes that with a playful call-out — teasing the contradiction between being “reformed” and still looking for mischief. That subtle challenge creates flirtatious tension. No compliments. No try-hard energy. Just charm with an edge.

Example 2

“Heard my Tinder match might be in Singapore. I wonder if she’s as fun as her photos suggest…”

• Why it works:

This gently suggests you’re not meeting just about any woman. You’re looking for someone fun. It’s a bit of a tease because you’re suggesting she may not be, while at the same time… hoping she meets your standards.

4. Assumptive Humor + Future Pacing

You speak as if things between you are already moving forward. It could be a cheeky date plan or a fake scenario. It’s bold, and it stands out.

Example 1

“[name], we may both be geriatric millennials, but I’m sure if you and I meet up for adventures, we won’t need any help moving around at all 😉”

• Why it works:

One of the lines in her bio: “geriatric millennial. I’m not young lol”. I made a cheeky assumption that we would meet and go on adventures. The “we won’t need help moving around” bit adds more mental images to a future date. It suggests you’re gonna have a good time. And there will be plenty of banter, at the very least.

Example 2

“Sounds like you’re on an exciting journey! I bet we can make the best memories for you in SG 😉”

• Why it works:

I cheekily suggest I can help her make the best of her time while she’s in Singapore for a month. It immediately assumes we’re gonna have a great date. Maybe more. It’s a risk to say that so quickly, but you can always pull back if she’s not as receptive.

5. Playful Compliment with a Twist

Standard compliments are boring. This technique takes a compliment and plays it off as a prediction. If she agrees with your compliment, you can then lead your interaction towards a Foreshadow.

Example 1

“I bet the T in your username stands for Terrific 😉”

• Why it works:

I suggest she is terrific, and she replies that she can be “t-errible at times”. This little fun bit allowed me to keep the playfulness up while leading the conversation towards a date.

Example 2

“If it helps you continue looking good in your dresses, then yes, let’s hit the gym all the time 😉”

• Why it works:

Her bio: “seeking my person who can be my gym buddy”. I used my compliment to foreshadow future dates. This allows her to imagine what our dates can look like, while giving me the opportunity to play off my own opener in my next few replies.

Final thoughts: Why these openers work on any dating app

Any opener can work. Even a plain “hey” can get you a reply. But the question is, if you send “hey” to 100 matches, how many will actually respond?

So the success rate is key here.

These 5 techniques work extremely well simply because they had one goal:

To increase your success rate by being playful first. It’s a classic “one step back, two steps forward” approach. And it works because almost every other guy is being too serious on the apps.

Most men try to “get to know her” right away by asking about her interests and other details that help them get the date.

But when you are being playful, you instantly separate yourself from the noise. You are telling her you are different, and not overly eager to get her out in under 5 messages.

Because you’re fun to talk to.

When a woman feels good talking to you…

She replies faster. She invests more.

But with just a little shift in how you open — as well as approach the entire interaction — you can finally start getting the dates you’ve been hoping for.

[Also read: The Simple Guide to Great Openers]