50+ Expert-Backed Dating App Conversation Starters

Make a great first impression with a thoughtful icebreaker

Written by Lisa Shield | Edited by Dev Murphy, MA

Last Updated: July 5, 2024 Fact Checked

You’ve matched with the cutie of your dreams on Bumble or Tinder—now all that’s left to do is slide into their DMs! But how do you strike up a convo in a way that’s fresh and original, and how do you keep the conversation going? To help you make a positive and lasting first impression, we’ve assembled expert tips for breaking the ice on a dating app, plus over 50 customizable scripting ideas to help get you started. Get ready to meet your soulmate!

This article is based on an interview with our professional dating and life coach, Lisa Shield. Check out the full interview here.

Things You Should Know

Ask your match questions about something they wrote in their profile to show you’re interested in them and share their interests.
Play “Would You Rather”—it’s a fun way to learn more about one another and see if you’re compatible.
Be direct and ask what they’re looking for in a relationship, or share what you’re looking for.

1

Ask them about something they put in their profile.

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Acknowledging their profile will show you’re invested in them. In the modern age, we’re all just swiping and swiping and swiping through profiles, so take the time to really look at what someone’s written in their bio—mean a lot. Plus, studies show people love to talk about themselves if given the chance!^{[1]
X
Research source} Break the ice with the hottie you’ve matched with by pointing out something specific you noticed in their profile and asking them more about it.
- “So you were in Maine over the summer? I’ve never been! What’s it like?”
- “Ah, so nice to meet someone else who loves Buddy Holly as much as I do! What’s your favorite song?”
- “Your dog is adorable! What’s her name?”
- “Correct me if I’m wrong, but is that Nicky’s Thai Kitchen in the background of one of your pics?? I love that place! What’s your fave thing to order?”
- “Didn’t think I’d meet another University of Akron grad here! What did you study?”
- “You work at an art museum? That’s so interesting! What’s that like?”
- Reader Poll: We asked 277 wikiHow readers how they initiate conversations with people online, and 49% said they talk about something on their profile. [Take Poll]

2

Play “Would You Rather.”

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"Would You Rather” is a great way to learn more about their personality. It’s not only a fun, lighthearted game; it really gives you insight into the way someone thinks (and gives them insight about you too!). Next time you match with a hot single, make a lasting impression by opening with “Would you rather…”
- “...be a dog or a flower?”
- “...live for 20 years or live for a hundred years?”
- “...live by the ocean or in the forest?”
- "...get up early or stay up late?"^{[2]
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- “...have 10 kids or no kids?”
- “...spend the next 20 years as a student, or as an employee?”
- “...live in a world where there is no crime or no privacy?”
- “...live next-door to your parents or live on the other side of the world from them?”
- “...drink coffee or tea forever?”
- “...know everything about one thing or a little bit about everything?”

3

Ask open-ended questions.

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Open questions give them the chance to say whatever they want. This will help you learn more about them—and it’ll take some pressure off of you to be a great conversationalist! Ask broad questions and follow up with prompts that indicate you’re invested, like “Tell me more about that!” It's a great way to get someone to open up and feel more comfortable.
- Stay on topic rather than jumping from new question to new question, or else it could come off like an interrogation. ("What's your family like? What's your job like? Where did you grow up?") And, talk about yourself now and again!^{[3]
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- “What’s your job like?”
- “What’s special about your hometown?”
- “What’s something you’re looking forward to?”
- “What was your worst first date?”
- “What’s the weirdest thing you find attractive in another person?”
- “What’s your favorite and least favorite thing about dating?”
- “If you could go anywhere in the world, where would you visit?”
- “What’s your best childhood memory?”
- “What’s your ideal day like?”
- “If you could hire someone to help you with cooking, cleaning, or yard work, which would it be and why?”^{[4]
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4

Ask what they’re looking for.

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Make sure you're looking for the same thing from the get-go. There’s no harm in being proactive with your icebreaker! Ask what they’re looking for in a relationship (if they’re looking for a relationship) to help you determine if it’s worth pursuing a first date with them. Are they looking for something long-term? A summer fling? Getting right to the point can save you both some time, but be sure to say “hello” first to avoid coming across too brusque!
- “So, what brings you to the dating app world?”
- “Are you more interested in a deep connection or just a casual thing?”
- “Do you see yourself settling down eventually?”
- “Can you describe your ideal partner?”
- “What does your ideal romantic future look like?”
- “What are you looking for in a relationship?”
- “Are you looking for something serious?”

5

Talk about what you’re looking for in a relationship.

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Let them know what your intentions are off the bat. If you're hesitant to ask them what they’re looking for, just let them know what you’ve got in mind yourself! Are you looking for a serious relationship, are you here for just a casual fling, or are you just along for the ride?
- “Hey there! I’m looking for something that has potential to become a long-term thing—that OK with you?”
- “Hi! I just moved to town and would love to meet some new people and get the lay of the land.”
- “What’s up? If you’re looking for a chill situation, I’m your gal.”
- “I just want to say off the bat, I think you’re super cute but I’m not looking for anything serious at the moment, hope that’s all right.”
- “Yo! Glad we matched. Just want to say I’m looking for a real connection here. No sweat if you don’t vibe with that, but I wanted you to know!”
- “Hey there, just wanted to say I recently got out of something serious, so I’m not really looking for anything too deep at the moment!”
- “Hi! You seem super cool, but you should know off the bat that I’m moving in a few weeks, so I’m not looking for anything serious!”
- “I should warn you I’m actually only here visiting my folks for the summer, but if this goes somewhere I’m open to a long-distance thing if you are.”
EXPERT TIP

John Keegan
Dating Coach
John Keegan is a Dating Coach and motivational speaker based in New York City. With over 10 years of professional experience, he runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health.

John Keegan
Dating Coach

A light and humorous tone is great if you're seeking something casual. When you keep your bio playful and fun, it lets potential matches know that you're looking for something casual, not a long-term commitment.

6

Ask a deep, meaningful question.

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Get up close and personal to learn who they really are. Lots of people appreciate small talk as an opportunity to get comfortable with one another before getting into a more serious topic. But asking a deep question right off the bat can help you learn more about them sooner. Plus, their willingness to engage in a personal conversation with a stranger can give you a sense of how open their personality is.
- That’s not to say it’s a red flag if they choose not to get too deep with a stranger—they may not feel comfortable talking about certain deep subjects, or they may just be shy.
- “What’s been your most meaningful life experience so far?”
- “What, in your opinion, is the most pressing political issue today?”
- “Have you ever wanted to run away and live a different life? Where would you go?”
- “How much of your present life lines up with what your child self imagined? Would you change anything if you could?”
- “Who is your number-one hero?”^{[5]
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- “What is the best gift you’ve ever been given?”^{[6]
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- “What really makes you angry?”
- “What’s your proudest accomplishment?”

7

Make a date.

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Kick it old-school: plan a first date and get to know them IRL. Skip over the virtual get-to-know-yous and jump ahead to the asking-out portion of the chat. You can get to know each other in person over your favorite pizza or a game of darts. (Just make sure you meet in a public place and tell your friends where you’re going!) Even if it turns out not to be a match made in heaven, who knows? You may still have a great time. And if not, you’ve got a good story to share on a future first date.
- "Let's get coffee" might be your go-to first date, but if you don't know someone well (or at all), it can be a little awkward just sitting there. Try to make your first date somewhat activity-based, like mini-golfing or a walk in the park (with coffee) to give you both something to focus on.
- “I’ll get right to the point—you seem cool, and I’d love to get to know you better off the app if you’re game!”
- “When's the last time you've been putt-putt golfing? Follow-up question: what are you doing tomorrow?”
- “My friend’s band is playing at a bar in South Side tonight! I know we don’t know each other, but are you up for an adventure?”
- “You and me, farmer’s market, tomorrow afternoon? I’ll buy your produce.”
- “What do you say we roll the dice and make a date right now? Talking in person is so much easier than messaging—and we’ll have ice cream, which makes everything better.”
- If you’re not up for getting together in person, ask to chat on the phone: “If ya want to get a little old-school, here’s my phone number—let’s talk!”

What Are Conversation Topics For Talking to Someone You’re Attracted to?

Join the Discussion...

What do I actually ask someone about on the first date?

WikiBirdWatcher823

Hi, so I haven't really gone on a ton of dates but the ones that I have gone on have kind of stalled while we're talking. I want to be able to ma... Read More

WikiTigerDancer210

I've been on my fair share of first dates, and I've always appreciated when the person I'm with asks me questions that go beyond the "basics." He... Read More

WikiCassowaryCatcher684

I like asking the question "What do you like to cook?" This is an approachable question that can help you learn a lot about a person and open up... Read More

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