Everyone has felt that dread well up inside when trying to think of something clever or cute to say to their online match and coming up empty…or worse yet, cringey.
While it’s true that you can’t say the wrong thing to the right person, it doesn’t hurt to stack the deck in your favor by using some online dating icebreakers that will get you noticed and spark conversation.
Remember, this could be your future person, and with just a little more effort, you can increase your chances of a response exponentially.
And if you’re a woman messaging a man, you’re in luck! When I was working as the official dating coach for OkCupid, I pulled data on messaging and found that conversations lasted twice as long when women initiated the first message.
There are four main ways to create conversation with a stranger online. I call these the messaging 4Cs: connection, controversy, compliments, and curiosity. (Don’t feel pressured to try all of them at the same time, just pick one that resonates for you and see how it lands.)
1. Make a CONNECTION: Comment on Their Profile
The easiest way to stand out from the crowd online is by making a meaningful effort to read their profile and connect. Shockingly simple, right?
As the number of users has risen on dating apps, the number of app matches, messages, and date options has also increased for most users. That means your first impression is even more important.
The deluge of matches and the endless swiping can create overwhelm and drive people to be lazier and less invested in the process until they see interest from the other person.
This thinking is flawed because if you don’t stand out as unique, thoughtful, or interested at first, there’s nothing the other person has to respond to, other than maybe a cute face and a few pictures.
To break through the noise, you need to send messages that create intrigue and inspire a response.
My easy formula for this is Comment + Question. Once you have a match, read their profile thoroughly and find one thing that resonates with you. Then your icebreaker is simply one comment about what you see in the profile and one follow-up question.
Example: I love your photo from Italy! What was your favorite part of the trip?
If you do this, you are connecting on a topic that already is important to them (I mean, if they chose to put it in their profile it has to have some significance.)
Plus, studies have shown that asking follow-up questions makes you seem more likeable. This one-two punch increases your chances of a response and can lead to additional follow-up questions on both sides.
2. Be CONTROVERSIAL: Stir Things Up & Get a Reaction
You always want to keep initial conversations light… but that doesn’t mean that you always have to agree. People love sharing their opinions. An excellent icebreaker is to create some friendly controversy over a topic that is not very serious.
This can either be a reaction to something on their profile or a question that you pose to them.
Example A: Unpopular opinion: Avocado toast is not worth $12.
In this example, a bold statement is made. But it’s not going to make the person angry or reactive. It will simply inspire them to respond, especially if they mention avocado toast or have it in a photo.
In the controversy category, you can be in agreement with them — it’s you and them vs. the avocado toast lovers of the world — in which case you can amp each other up about reasons for your unpopular point of view.
Alternatively, you can be in opposition to their perspective or give them a question that would provoke playful banter.
Example B: I can’t tell from your photos so I have to ask: morning person or night owl?
Here you aren’t taking a side necessarily, but you are asking a “This or That” style question that is bound to get a response.
You can make a “This or That” about nearly anything: Coke or Pepsi, mountains or beach, chocolate chip or peanut butter cookies, potato chips or fries. The list goes on.
As long as you pick something light and keep the banter friendly, you can jump-start a conversation quickly.
3. Give COMPLIMENTS: Can’t Go Wrong With a Little Flattery
The idiom, “Flattery will get you nowhere”, couldn’t be more wrong, especially if you’re giving the right kind of compliments and noticing the qualities that actually matter to someone.
Everyone wants to feel seen and special on a dating app. A sincere compliment is the easiest way to break the ice and let someone know they caught your eye.
The key is that you should not go for the low-hanging fruit of flattery. If it’s a compliment they get all of the time, it’s not the kind of message that will stand out from the crowd.
Look beyond the surface level and find something unique to highlight. Bonus points if it’s not something physical.
If someone took the time to craft a witty response to a dating app prompt, call them funny, tell them how clever they are, let them know they are clearly both smart and beautiful. That will go a lot further than saying they have great hair or a nice smile.
Dating Horror Story from the Damona files: I once had a client who struggled with compliments. I knew I had my work cut out for me when he showed me his latest message to a woman in which he said, “You have great teeth, like a horse!” This missed the mark by both giving an easy physical compliment and comparing her to an animal. A beautiful and beloved animal, but an animal just the same.
Once you open with a compliment to get their attention, follow up with a simple question to take the conversation deeper. And if the topic is funny, quirky or intriguing in a non-sexual way, even better!
Example: I’ve never pitched a tent, so I’m really impressed by your camping skills. How do you think you’d do in a zombie apocalypse?
4. Be CURIOUS: Ask a Thoughtful Question!
As discussed in my book F the Fairy Tale, the quality that drives connection should never be chemistry; you’ll get a lot further following curiosity.
Before you send that first message, scan their profile again and ask yourself:
- What am I curious about?
- What more do I want to know about this person?
- Which elements of their profile probably have interesting stories to accompany them?
You can also use the comment + question formula for this type of icebreaker.
This differs from connection because it doesn’t have to be any topic that you know anything about or have direct experience with.
Couples really only need to have one or two common interests to sustain a long-term relationship, but if you care and are curious about the other person, that is an endless well of relationship discovery.
Example: A pickleball player! I never got into the craze, but I’m curious, is it anything like tennis?
When You’re on the Apps, Speak Your Truth
Many times, people have thin or hastily created profiles. So what do you say if the profile has nothing meaningful to go on?
First, I would ask what is driving your interest in that person. If it’s just physical, perhaps this is not someone you want to invest in.
However, if there’s something else, remember that anything in the profile is fair game for an icebreaker, including job, location, school, and other basic details.
If you are on Bumble or an app that already seeds an icebreaker or introductory question, try to apply one of the 4Cs to differentiate yourself from the volumes of similar responses they’re likely receiving.
The key when you shoot your shot is to not get too invested in the outcome until you are actually in conversation. Sometimes it takes a follow-up message to get banter going, but you never want to be in a place of chasing or always being the first person to reach out or to ask questions.
The icebreaker is the easy part because you truly have nothing to lose at that beginning phase. You don’t know the person and may never see them again.
Many people stop themselves from sending that first message because they don’t know what to say, they don’t think they should have to make the first move, or they don’t want to invest too much and get rejected.
Ultimately, those are the people who tell me online dating doesn’t work. And they end up sitting on the sidelines.
I’ve helped thousands of daters, and I’ve seen the same story time and time again. Those who initiate consistently see better results than those who wait for the magic to happen. Be the chooser, be brave, be bold, and don’t be afraid to stand out from the pack.
