40 Ways To Initiate An Actually Good Conversation On A Dating App

Because saying “hey” probably won’t get you very far.

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These good opening lines will help you start a conversation on a dating app.

It can feel really awkward to start chatting with someone on a dating app. Everything feels cheesier and forced when you're trying to get the conversation going, but it's like ripping off a Band-Aid — soon, the hard part will be over and you'll feel so much better. So if you find it difficult to send the first message, it can help to have some good opening lines on hand.

"Whether you choose to initiate the conversation on a dating app or face-to-face with someone you're interested in, it's always important to have a great conversation starter in your back pocket," Kate MacLean, a resident dating expert at PlentyOfFish, tells Bustle. "A thoughtful question or reference to your date's hobbies and interests will likely result in an exchange of information that can tell you a lot about someone and, more importantly, whether you're compatible or not."

As a basic rule, asking a question or something that suggests they send a reply is much better than just a statement — which can be easy to ignore. And, of course, the best opening lines use a little humor. So if you're not sure how to get started, think about things you can ask them based on their bio — or try one of these opening lines, which are all so much better than "hey."


"What's Your Theme Song?"

How a person answers this will tell you a lot about them. Will they make a joke or do they take themselves very seriously? Also, a little glimmer into their music taste is always helpful.


"How Would You Describe Yourself In Three Words? How Would Your Friends Describe You In Three Words?"

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Not only does this question let you get to know them, but the contrast between how they describe themselves and what their friends would say can be very interesting.


"Cheese, Pepperoni, Or Hawaiian?"

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It's important to get down to the hard-hitting political issues, right from the start. Better to see if your ideals are aligned now rather than later.


"What's The Worst Opening Line You've Ever Received?"

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Most anyone with experience online dating has had some humdingers, so this will likely give you a chance to trade some dating app stories.


"What's The Best Place You've Traveled?"

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If you're someone who loves to travel, then getting an idea of where they like to go is a great way to start the conversation and gauge compatibility.


"What's The Worst Date You've Ever Been On? Mine Involved..."

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Sometimes you have to give to get. Sharing an awkward event from your life can help the other person feel more comfortable opening up to you about a funny or embarrassing experience.


"We're Married. I'm Complaining That I Don't Know What I Want To Eat. You Suggest...?"

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The answer to this question may define the rest of your life — best to get it out early. You can also tell a lot about a person based on their taste in food.


"What Three Characters Combined Best Describe You?"

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As long as the answer isn’t any of the characters from Succession, you’re probably in the clear.


"Why'd You Swipe Right?"

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If you want to cut right to the chase about what the other person might be interested in and get the ball rolling, ask them why they said yes.


"When Sharing Ice Cream, Do You Dig Out All Of The Best Parts Or Share Them Equally?"

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This question divides friendship groups, lovers, and countries (probably). Learn if they're going to dig out all of the cookie dough or save some of it for you. Find out now, before it's too late.


"What Show Are You Marathon Watching Right Now?"

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Get some insight into whether or not you're going to fight over the remote — and maybe you'll even get some good recommendations out of it.


"What's Your Favorite Book?"

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If you're an avid reader (or just want to look like one), start out the conversation on a literary note.


"Are You A Stark, Lannister, Baratheon, Or Targaryen?"

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If you're a Game of Thrones fan (or a House Of The Dragon fan), this will be a great way to learn more about their personality.


"What's The First Thing You Do When You Wake Up In The Morning?"

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Being an early bird or a night owl can make a big difference in a relationship — just ask anyone who's shared a bed with someone of a different sleep chronotype. Seeing how they tackle their mornings can also be a fun way to learn more about them.


"Why Did You Pick This App?"

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There are a lot of different dating apps out there, so finding out why they went with this particular choice can help you understand what they're looking for and see if you're on the same page.


"What's Your Idea Of A Perfect First Date?"

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A good way to set the scene for things to come. Plus, getting a sense of their dating style can be really useful.


“If You Could Switch Lives With A Celebrity For A Day, Who Would It Be And Why?”

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Getting to see what celebrities someone is at least mildly interested in can be very telling about what kind of pop culture they’re consuming and their interests.


"What's The Best Opening Line You Can Think Of?"

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This one's a great choice when you're interested but want them to take the lead. If you’re used to sending out opening lines, sometimes it’s fun to sit back and let others take the first leap.


"Favorite Sunday Activities?"

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Depending on your work schedule, Sunday is often the day of no ties and no obligations, where you can totally design the day how you want. Getting an idea of what they like to do can be really telling.


"What Meme Best Describes You And Why?"


Whether they're a recent Twitter or TikTok meme, or a classic "This is fine." meme, you'll get a sense of how they view themselves, as well as their type of humor.


"What's The Worst Nickname You've Ever Been Given?"

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Get some insight into their personality. Nicknames are normally there for a reason, and they tend to stem from a great story.


"Most Embarrassing Childhood Memory? Mine Is..."

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This is another conversation opener where it can help to give a little first. Simply share an embarrassing story and see what comes back.


"You Have 72 Hours Left On Earth. What Do You Do?"

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They might go full-out while trying to save the world, or they might hide out and eat pizza and pleasure themselves for three days. Either way, it can kick off a fun convo.


"Standard Greeting, Harry Potter Pickup Line, Or Rap Battle?"

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This was an actual message someone was sent, and we can all only hope that they lived happily ever after.


"How Many Different Pasta Shapes Can You Name?"

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If they can only name one or two, follow up by asking what they like to cook. And just like that, you'll have a first date idea.


“I’m Letting You Assume One Thing About Me From My Profile: Go.”

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A classic premise taken from a party icebreaker game, this line gives them the chance to tell you what they think of you just based on your pictures and bio, which can be very illuminating and, hopefully, amusing.


“If You Could See Any Movie For The First Time Again, What Would It Be?”

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This is basically a creative way to ask what someone’s favorite movie is without sounding like a drag. And maybe it can even lead to a movie night date.


“What’s Your Go-To Karaoke Song?”

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Knowing someone’s favorite karaoke song is incredibly revealing. If they don’t have one at all? Red flag. Not to mention, this line sets you up perfectly to suggest a karaoke meetup.


“If You Could Be On Any Reality TV Show What Would It Be?”

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Their answer to this will reveal A. what kind of shows they’re into, B. what their general interests are, and C. if they’re competitive or not.


“Guess What My Drink Order Is And I’ll Guess Yours.”

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Everyone loves a little two-way guessing game. And if you’re not into alcohol, just sub in the words “coffee order,” “bagel order,” or whatever feels right to you.


“Wait, I Need To Know So Much More About [Profile Detail]”

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Use a standout detail from their profile for an easy conversation starter. Dating coach Alison Marie tells Bustle, “Starting off a message like this not only is flattering to the person receiving it, but also shows an attractive level of confidence.” You know what you like, and you aren’t afraid to go after it.


“Where Are We Going On Our First Vacation?”

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“If someone's idea of an adventure is a camping trip while another person’s is traveling to different countries and staying in five star hotels, there might be little compatibility,” Marie says. “But if you bond over experiences and have similar interests, this can help spark a connection and deepen conversation.”


“What Does Your Ideal First Date Entail?”

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According to Marie, “Getting an idea of someone's first date is a fun way to open the conversation and see what they like to do.” Bonus points if you have similar answers — you’ll have an easy plan for your first outing together.


“Your Dog Is So Cute! We Should Take Our Puppies To The Park Sometime.”

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This demonstrates both confidence and a mutual interest to connect with, Marie explains. We all know how invested pet parents can get, so if you both have dogs, go for it!


“What Are You Most Passionate About?”

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Marie recommends this message to get a sense of your matches personal values, and see if they align with yours. On dating apps, it’s easy to bond over a mutual love of Rick and Morty, but that doesn’t exactly set you up for long-term success. Asking deep, meaningful questions like this right off the bat will help weed out matches who aren’t a good fit.


“Describe Yourself In 3 Emoji”

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Emojis keep things light — but also interesting. Whatever three they choose opens up a ton of room for conversation as you’ll get a sense for their interests and personality.


“What Are Your 3 Most Frequently Used Emoji”

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Similar to above, this question is a low-lift, fun way to get a sense of their interests, and it leads to a ton of follow up questions.


Let’s Settle This Once & For All: Is A Hot Dog A Sandwich?

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If you want to skip the small talk and head into a silly debate, see how they feel about this (very important) topic that leaves a ton of room for banter.


What’s Your Guilty Pleasure? I Won’t Judge If You Don’t Judge Mine!

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Here’s a quick way to lighten the mood and bond over sharing potentially embarrassing things about yourselves.


Which Actor Would Play You In A Movie About Your Life?

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This fun opening line gives you a sense of their personality and leaves room to learn more about who they are — What would the movie be called? What’s the soundtrack? Where would it be filmed?

There's no perfect opening line for dating apps, but having a few funny ones or good questions in your pocket can make a big difference. If you want to get a response, notice things in their bio or stick with questions. Dating is, after all, about getting to know each other.


Kate MacLean, resident dating expert at PlentyOfFish

Allison Marie, dating coach

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