8 Ways to Initiate a Dating App Conversation to Spark Interest and Get Them Hooked

Matching with a person who seems like a perfect fit for you on a dating app is such a thrill. You have the same interests, you love the humor in their prompts, your astrological signs are compatible, and they have an adorable cat! Wow, fingers crossed.

Now comes the million-dollar question: do you wait for them to reach out or initiate a conversation? This task seems like it should be easy. Just type out a quick hello and hit send. But as you stare at that blank text box, the stakes start to feel high, and the pressure is suddenly on to make a good impression. You want to come off as witty, fun, intelligent, and funny all at once, and you're convincing yourself that a simple hello will not cut it.

But in all seriousness, if you decide to go with a simple hello, that’s totally fine. Online dating is stressful enough, and who needs the added pressure of crafting a compelling opening line with every match? 

On the other hand, think of all those cringe-worthy first messages and failed attempts at humor you’ve gotten from potential connections in the past. How quickly did those conversations fizzle out? So why not take charge and break the cycle? Put some thought into initiating a conversation and remember that, just like you, the person on the other side is hoping for a real, meaningful connection.

Why Is Starting a Conversation So Dang Hard?

It’s a question as old as the very first dating app, and I’m talking about newspaper ads, not Match.com. Starting a conversation with a stranger feels hard enough; starting one with someone you hope to fall in love with is significantly more challenging. With online dating, your competition isn’t a few other single people in a bar. You’re up against hundreds, maybe thousands, of people who have potentially matched with this person you hope is “the one.”

The competition to get someone’s attention on dating apps has never been higher than today, so just starting with a single “hi”, which is perfectly acceptable, is less likely to get you a response. "Sure, your aura and looks have already made someone interested in you, but now you need to make them hooked with an interesting, entertaining conversation," says Sofie Roos, a licensed sexologist, couples therapist, and author at Passionerad.

Every time I’ve used a dating app, a single message could be the difference between me hitting reply instantly or relegating the sender to the grave of seen and ignored messages. Being guilty of this is why I often found myself overthinking every word, punctuation mark, and emoji.

And the fear of rejection is even more terrifying than making a good first impression. No matter how often you tell yourself it’s “not a big deal” or “it’s just a stranger on the internet.” The fear of putting yourself out there and getting ghosted or getting a snarky reply can make even the most confident person balk. 

According to some reports, about 3 in 10 American adults have used a dating app or site at some point. That’s millions of people every year, which in theory results in a near-endless supply of potential matches. However, while that might sound like an ideal scenario, it often creates the paradox of choice—where too many options make it harder to commit to just one.

"Traditional gender norms and stereotypes also play a role, potentially affecting how eager we may be to be the first one to dive into the conversation," says Kiana Reeves, a somatic sex educator, and Foria’s Chief Education Officer. 

Decoding your Match’s Profile

It'll be easier to initiate a conversation if you dig deeper into your match’s profile. The reality is when we’re swiping, we make many split-second decisions. I once swiped right on a guy because he was wearing a t-shirt of a band I loved, only to find a dozen red flags on his page when we started talking.

Taking the time to go through their profile helps you figure out if they’re even worth your time, but you’ll also get a lot of great material you could use to start a conversation. It may seem like a no-brainer, but how often people skip this and go straight into a conversation will surprise you.

"I first recommend looking through this person’s demographic info, bio, and photos; is there anything in their bio or prompts that indicates an overlap in interests, hobbies, or values?" says Reeves.

Do they love hiking? Are they obsessed with a particular TV show? These work perfectly for an opener message. For instance, you could say, “I saw you love hiking! Do you have a favorite trail? I’m always looking for new places to explore.” You could also reference something niche you’ve seen on their profile, like a photo of them in a foreign city. You could go, “I noticed your photo in Tokyo; I’ve been dying to visit!” Don’t get caught up in surface details like how they look or their job; try to go deeper. 

What do their photos or bio say about their personality? Are they adventurous, creative, or a goofball? Doing this doesn’t just help you better connect with them; it lets you take a second to properly vet a potential romantic connection before jumping into another talking stage. 

How to Write the Perfect Opening Message

You’ve done all your homework, now comes the time to get the conversation going. Here's how to create the perfect opening message:

Ask open-ended questions

Open-ended questions are a cheat code for initiating conversations on a dating app. They nudge the other person to share more about themselves and show that you’re genuinely interested in getting to know them.

These types of questions show you’re interested in their passions and give them a chance to share something they’re enthusiastic about. Especially in the first few days of talking to someone new, it’s important to strike a balance between having a robust conversation and still saving some topics for a potential first date. 

With that in mind; it’s important to try to ask open-ended questions, as you would in any conversation, to make the most out of this texting phase and to avoid driving the entire conversation, Reeves adds.

Get personal but not too personal

If you want to stand out, look for something niche in their profile that will allow you to get a little more personal. This could be a poster behind them in a photo or a tattoo you noticed on their arm.

If it’s a thing you relate to, reference that or ask them what inspired the tattoo. A personalized message shows that you’ve read through their profile, found something interesting, and want to know more. It’s a great way to make them feel special from the start.

When all else fails, use humor 

Opening with a joke is a fantastic icebreaker. If it’s important to you that your partner has a sense of humor, it lets you know right off the bat that they have one and can instantly lighten the mood.

Just be careful with what you choose to joke about. Humor can be subjective, and what seems funny to you might not land the same way with someone else. So, keep it light and fun, and avoid anything that could come off as controversial or inappropriate.

Foolproof Conversation Starters

Now you’ve come up with the perfect opener, fantastic! But what do you do when the conversation stalls or comes to a natural end? How do you restart it in an easy, breezy way? Here are some conversation starters (or restarters) you can keep in your back pocket. 

Questions about their interests

These are perfect if they’ve mentioned a specific hobby or passion you haven’t talked about yet. For an artist, you could say, “You mentioned you love painting—what inspires you the most when you start a new piece?” Given the chance, most people are happy to talk about themselves, and these questions also show you’re genuinely interested in what they love and allow for deeper conversations.

Light-hearted debates

Not about politics and never religion, at least not just yet. I’m talking about playful debates like what ice cream flavor is the greatest and whether pineapple on pizza is yuck or yum. Questions like these are easy to answer and can be fun to see if you have a compatible sense of humor.

“This or that” questions

Quick and simple “this or that” questions are a great way to keep the conversation light and fun. They’re non-intimidating and can also quickly reveal what interests you share.

Hypothetical scenarios

These are great if you’re up for getting creative. You could ask them what three people, dead or alive, they’d want to have dinner with or what superpower they want and why. Hypothetical scenarios are always fun and can provide hours’ worth of conversation material.

Compliment + question combo

Start with a genuine compliment and follow up with a question to keep the conversation going. For instance, “You’ve got a great smile! What were you laughing about in that photo?” Compliments make people feel good, and pairing them with a question shows you’re interested in learning more about them.

How to Recover from a Rough Start

Not every first conversation will play out like a movie scene. Maybe your first message didn’t land how you hoped, or the conversation started strong but is now fizzling out. Don’t panic; an awkward conversation doesn’t have to mean the end of a potential connection.

Sometimes, the best way to handle a rough start is to call it out light-heartedly. Acknowledge the awkwardness and ask for a reset. I’ll bet the other person would jump at the chance for a do-over. Owning up to the awkwardness can be endearing and shows that you’re not taking yourself too seriously. 

If things are fizzling...

Try steering the conversation in a new direction. You could bring up a new topic or ask a question that reignites their interest. People also love sharing their opinions and asking for advice can be a great way to re-engage someone who’s lost interest. It doesn’t have to be anything serious, just something that gets them thinking and talking again.

The best way is to move to a blank page by asking something fresh, such as “Tell me something that stood out with your day today, weird, funny, or something else.” That way, you leave the old conversation behind naturally and keep moving forward.

You can also be honest with why you got a bad start and turn it into something positive, for example, by saying, “I got nervous because you really caught my interest and you seem like my type, so I kind of screwed this up. Can we start over from zero?”. Then you combine a compliment and a restart, which is quite smooth, says Ross.

If things feel dull or awkward...

If the conversation has taken a dull or awkward turn, try using humor to lighten things up. Share a funny story, a meme, or a light-hearted joke related to something they’ve mentioned. Humor can quickly shift the mood and make the conversation fun again. It also shows you’re not afraid to be playful and silly. However, a gentle follow-up is okay if you’ve sent a message and haven’t heard back. Keep it light and low-pressure, and give them an easy out if they’re uninterested.

If They're Just Not Interested, Cut Your Losses and Move Forward

Not every dating app match will be the one or even lead to a date, says Reeves. That’s what’s exciting about them in the first place; they promise a lot of possibilities and make it easy to see how many fish in the sea there truly are.

If someone indicates they’re no longer interested, even after successfully matching or chatting, they do so out of respect for you and your time. Try not to take it personally—there’s only so much you can learn about someone from behind a screen, and there could be 100 other things going on in their life as well (perhaps they went on a great series of dates and want to give that person a shot). Rejection is also a part of life—it will ultimately bring you that much closer to the person who you could end up dating next!

Starting a conversation on a dating app doesn’t have to send you spiraling; there’ll be plenty of time for that later (okay, hopefully not). The most important thing is to remember to be true to yourself, patient, and willing to laugh at yourself when things don’t go perfectly. Embrace the awkward moments, as there’ll be many, and let your personality do the heavy lifting. The right person will appreciate the real you, not a perfectly curated version.