How to craft a perfect opening message on a dating app

A foolproof method

“The one” that could have been haunts us all. Not the person, but the perfect opener you wished you had sent instead. Here’s how to land the perfect opener every time.

You’re a conversational genius. You’ve crafted a flirty opening line that is so perfect, so demure, ney, so ahead of its time that it defies cutesy trends. And you did it solo, without consulting the group chat.

It’s a masterpiece of brevity, humour, elusiveness and just the right amount of profile throwback. It’s somehow cute and sexy, the golden ratio of flirting. Somebody should teach it in schools and scribble it on bathroom stalls, for it is proof enlightenment is possible.

But it’s twelve hours too late. And you already sent another opening message to your match. Your new line puts it to shame, of course: it looks weak, childish and pathetic in comparison. But you can’t double-open, especially when they haven’t replied (yet). Now, you’re both disgusted at your past self and haunted by your brilliance.

In Seinfeld, this is George Costanza’s “jerk store” moment: the perfect line that hits after the fact. And on dating apps, it’s a maddening weekly occurrence.

The delicate balance of an opening line

Crafting a great opener is finding a spot between spontaneity and impact. It should sound like you, or at least the “you” you want to sound like. Ideally, it’s cheeky, playful, and effortless (even if it took work).

But here’s the truth: the “perfect” line is a myth because so much is out of your control. Your match must be in the right mood, have notifications turned on and be on the same humour wavelength. A genius opener is only part of the story.

And here’s the danger: too many regrets over unsent or unrequited openers can make you doubt whether it’s worth trying. Sure, skipping the message spares your rejection, but it also shuts the door on the “what ifs” that could come from even a “good enough” opener. So, always take the shot, even if it’s not “the one” – the line, not the person.

Here’s how to open a conversation with minimal regret and maximum authenticity. But first, let’s take a moment of silence: a tribute to all the brilliant unsent openers. They were missed by the intended recipient but never forgotten.

Here’s how to open a conversation with minimal regret and maximum authenticity. Image: Pexels

Tip #1: Notice, don’t impress

Assume every detail of their profile is akin to a Taylor Swift “Easter egg” and simply call it out. If they have a few holiday snaps, try, “Alright, world traveller, where’s the best place you’ve ever woken up?” It’s immediate, personal, and feels genuine.

If they’re in multiple group shots at gigs (and you’re sure you can tell them apart from their friends), ask, “So, who’s a worse influence, you or your friends?”

Tip #2: The rule of three

The rule of three is a straightforward comedy staple. You set a pattern with two similar phrases, then break the pattern for a plot twist. It’s perfect for a playful opener. Name a few similar themes from their profile, then put a spanner at the end to get them confused or intrigued.

If you’ve spotted yoga, hiking, and smoothies, you could say, “So you’re a yoga buff, mountain conqueror, and... secret karaoke master?” It’s lighthearted, unique, and often prompts a fun response.

Compliments work best when they’re unique. Image: iStock

Tip #3: Go bold, go random

Most of us are consuming content and swapping recommendations is an easy fallback. So why not take the same content consumption theme and flip the script? Ask, “What’s your Netflix algorithm trying to get you to watch?” or “What accidental rabbit hole led to your strangest sponsored ad?” These are easy to reply to and reveal some personality without getting deep. 

Tip #4: Compliment, but keep it fresh

Compliments work best when they’re unique. Rather than a generic “You’re cute,” try something that catches them off guard. If you’re vibing their dating profile’s Spotify integration, drop “You look like you’d pick a great road trip playlist.”

If they look social, “You strike me as the funniest person in your group”, or if they’re giving foodie vibes, try “You look like you know your way around a menu.”

Self-deprecation is a legitimate way to break the ice. Image: Getty

Tip #5: The awkwardness of it all

Self-deprecation is a legitimate way to break the ice. If you’re overthinking, admit it! And honestly, who isn’t overthinking on dating apps? Try, “(Name), I’ve spent minutes overthinking this opener, so feel free to overthink your reply,” or a slight sarcastic spin, “I’ve spent at least five minutes on this opener, so no pressure to top it.”

Tip #6: Channel the Barbie Movie

Take inspiration from the Barbie movie’s humorous approach to “mansplaining.” Try, “What’s something you’d gladly explain that I’d probably pretend to understand?” or “How likely are you to break down Inception if I asked?” It’s playful, allows them to show off, and opens the door for humour, regardless of gender.

Originally published as How to craft a perfect opening message on a dating app