A Dating Coach’s 4 Tips for Online Dating Openers

We’ve all felt the dread rise as we try to come up with something cute or clever to send an online match, only to draw a blank… or, even worse, land on something cringey.

Sure, there’s no wrong thing to say to the right person. Still, it can’t hurt to tilt the odds your way with a few online dating icebreakers that get you noticed and get a conversation going.

Keep in mind that this might be your future person, and a bit of extra effort can boost your odds of hearing back exponentially.

Women messaging men, you’re in luck! Back when I was OkCupid’s official dating coach, I dug into the messaging data and found that conversations ran twice as long when the woman sent the first message.

You can get a conversation started with an online stranger in four main ways, which I call the 4Cs of messaging: connection, controversy, compliments, and curiosity. (No need to use them all at once. Choose the one that feels right to you and see how it goes.)

1. Build a CONNECTION: Respond to Their Profile

The simplest way to stand out online is to put real effort into reading someone’s profile and connecting with it. Surprisingly easy, right?

With more people joining dating apps, most users are seeing more matches, messages, and date options too. So your first impression matters even more.

That flood of matches and nonstop swiping can leave people overwhelmed, pushing them to get lazier and hold back their investment until the other person shows interest.

The logic doesn’t hold up. If you don’t come across as unique, thoughtful, or interested from the start, the other person has nothing to reply to, other than perhaps a handful of photos and a cute face.

Cutting through the noise takes messages that spark intrigue and make people want to write back.

My simple formula: Comment + Question. When you match, read the profile carefully and pick out one thing that speaks to you. Your icebreaker is then just a single comment about something in the profile plus one follow-up question.

Example: Loving your Italy photo! What was the best part of that trip?

This way, you’re bonding over something that already matters to them (after all, if they chose to include it in their profile, it must mean something to them).

On top of that, research shows that follow-up questions make you come across as more likeable. This one-two combo raises your odds of a reply and can prompt more follow-up questions from both of you.

2. Get CONTROVERSIAL: Shake Things Up & Spark a Reaction

Early conversations should always stay light… but that doesn’t mean you have to agree on everything. People love to share their opinions, so a great icebreaker is stirring up a bit of friendly controversy over something that isn’t very serious.

It can be a response to something in their profile or a question you put to them.

Example A: Hot take: $12 is too much for avocado toast.

Here, you’re making a bold statement, but not one that will anger the person or put them on the defensive. It’ll just prompt them to reply, particularly if avocado toast comes up in their profile or appears in one of their photos.

With controversy, you might be on the same side (the two of you vs. the world’s avocado toast fans), and then you can hype each other up over why your unpopular view is right.

Or you can take the opposite side from them, or ask a question designed to spark some playful banter.

Example B: Your photos don’t give it away, so I’m asking: night owl or morning person?

You’re not really picking a side here. Instead, you’re asking a “This or That” question, and those are bound to be answered.

Nearly anything can become a “This or That”: mountains or beach, Coke or Pepsi, potato chips or fries, peanut butter or chocolate chip cookies. The options are endless.

Choose something light and keep the back-and-forth friendly, and you can kick-start a conversation fast.

3. Offer COMPLIMENTS: A Bit of Flattery Never Hurts

That old saying, “Flattery will get you nowhere”, is dead wrong, particularly when you give the right kind of compliment and notice qualities the person truly cares about.

On a dating app, everybody wants to feel special and seen. A genuine compliment is the easiest icebreaker there is, and it shows someone they caught your attention.

The trick is to skip flattery’s low-hanging fruit. A compliment they hear constantly won’t make your message stand out.

Dig past the surface and point out something distinctive. You get bonus points if it isn’t physical.

When someone has bothered to write a witty answer to a dating app prompt, tell them they’re funny, praise their cleverness, and let them know they’re obviously smart as well as beautiful. That gets you much further than complimenting their great hair or nice smile.

From Mia White’s Files, a Dating Horror Story: A client of mine once had real trouble with compliments. The moment he let me see what he’d most recently sent a woman, I knew this would be a tough job: “You have great teeth, like a horse!” It missed on two counts, offering an easy physical compliment and likening her to an animal. Sure, a beautiful, beloved one, but still an animal.

After a compliment grabs their attention, add a simple question to take things deeper. Bonus if the topic is quirky, funny, or intriguing without being sexual!

Example: Your camping skills blow me away, since I’ve never even pitched a tent. How would you fare in a zombie apocalypse?

4. Stay CURIOUS: Ask Something Thoughtful!

As I explain in F the Fairy Tale, my book, chemistry should never be what drives a connection; following your curiosity will take you much further.

Before sending your first message, look over their profile once more and ask yourself:

• What makes me curious?
• What else would I like to learn about this person?
• Which parts of their profile likely come with an interesting story?

The comment + question formula works for this kind of icebreaker, too.

Unlike connection, this approach doesn’t require a topic you know about or have firsthand experience with.

A couple needs just one or two shared interests to keep a long-term relationship going, but caring about and being curious about each other gives you an endless well of discovery.

Example: Oh, you play pickleball! The craze passed me by, but I’m curious: is it similar to tennis?

Speak Your Truth on the Apps

Plenty of people have sparse or rushed profiles. What should you say when there’s nothing meaningful to work with?

Start by asking yourself why you’re interested in this person at all. If it’s purely physical, maybe they aren’t worth your investment.

If there’s more to it, though, keep in mind that anything on their profile can be used for an icebreaker, including school, job, location, and other basics.

On Bumble, or any app that already supplies an icebreaker or intro question, use one of the 4Cs to set yourself apart from the piles of similar replies they’re probably getting.

When you shoot your shot, the trick is not to get attached to the outcome until an actual conversation is underway. A follow-up message is sometimes needed to get the banter rolling, but you never want to end up chasing, or always being the one who reaches out first or asks all the questions.

The icebreaker is the easy bit, since there’s genuinely nothing to lose at that early stage. You don’t know this person, and you may never cross paths again.

Lots of people hold back from sending the first message because they’re unsure what to say, think the first move shouldn’t be their job, or fear investing too much and getting rejected.

In the end, they’re the ones who complain to me that online dating doesn’t work. Meanwhile, they’re stuck on the sidelines.

I’ve worked with thousands of daters, and the pattern repeats itself again and again: people who consistently make the first move get better results than people who sit back and wait for magic. Be the one who chooses. Be brave and bold, and don’t fear standing out from the pack.