Dating App Icebreakers That Will Make You Laugh Out Loud

Happy Man and Woman Texting - 3D Mobile with Red Hearts, Happy Faces and a Megaphone

Dating app icebreakers are everywhere—there are too many to count. Platforms use these prompts to help singles get the convos going, and while that’s really helpful, some of them are overused and played out. It happens; there are only so many puns out there!

To be honest, making the first move is hard for most of us. It is awkward; you don’t know how it’ll be received, etc. That is why icebreakers exist—to break the ice (hello, it’s right there in the term). But the right one can turn a weird moment into an opportunity to get a good laugh! Or at least peak their interest.

Here is a good one that might not be hilarious, but it is super relatable: “If you wrote a book, what would the title be? Mine would be ‘Overthinking Opening Messages.”

It works on two fronts—it’s different that the usual ones, and it pokes fun at the awkwardness of messaging a match first.

Humor is a great way to make a strong first impression on dating apps—it lightens the mood and gives you a chance to let your personality shine, which makes the other person (hopefully) grin and feel more at ease.

We are going to examine all kinds of funny icebreakers and why they work so well! From witty one-liners to flirty questions, we are gonna help you nail the art of the humorous opener. Let’s find out how laughter can lead to love!

The Power of Humor in Online Dating

Humor is one of the most powerful tools in almost any situation—especially dating! It’s such a great way to make a good first impression and works in your favor to create a connection that feels natural. Laughter can cut tension and can turn an uncomfortable start into a fun and engaging convo.

two people texting with phone in between them

Breaking the Ice

Starting a conversation with a joke or clever comment can dissolve the initial awkwardness that usually comes with online dating. Humor makes both people feel more relaxed and open, and research from the University of Kansas shows that mutual laughter is a strong indicator of romantic interest. Men who can make women laugh are often perceived as more attractive, not just because humor is linked to intelligence but because it helps create a comfortable and fun interaction.

authentic connection

Creating a Connection

Laughter has always played a huge role in building rapport and connection. Why? Easy—it lights up the brain’s reward centers, making people feel good and more inclined to continue talking. Humor can help potential partners bond over common experiences, creating a foundation for a stronger connection. Studies indicate that couples who laugh together tend to have stronger, more fulfilling relationships.

Hand Holding a Magnet and Attracting Hearts and Likes

Standing Out

In the crowded space of online dating, a funny icebreaker can help you catch someone’s attention. After a time, dating profiles tend to become a blur of similar photos and bios. By adding some humor, you can make your profile much more intriguing. A well-placed joke or witty comment shows that you have a fun personality and are approachable. This can make potential matches more likely to engage with you and want to learn what makes you tick.

Types of Funny Icebreakers

In online dating, icebreakers are the first messages or comments you use to get the ball rolling in the DMs. A good icebreaker can help you make a good impression and start a meaningful interaction.

Puns and Wordplay

Puns are a clever and humorous way to start a conversation. Here are four punny examples you can try out:

  • “Are you from Central America? Because I can’t Belize my eyes.”
  • “Are you a library book? Because I’d like to check you out.”
  • “Do you like Star Wars? Because you’re the Obi-One for me.”
  • “I used to date a girl who was lactose intolerant. We broke up because she couldn’t stomach my cheesy jokes.”


Puns work in online dating for the following reasons:

  • Cleverness: Puns demonstrate wit and intelligence, which are attractive qualities that show that you can think creatively and make connections in unique ways.
  • Humor: Puns are inherently funny, and humor is a great way to break the ice. A well-timed pun can make your match laugh, helping to create a more relaxed and fun vibe.
  • Engagement: Because puns often involve wordplay, they can prompt a response. Your match might reply with their own pun or comment on yours, keeping the chat going.
  • Memorability: A good pun can make your message stand out in a flood of generic openers. It’s more likely to be remembered and appreciated, giving you an edge over other messages your match gets.

By incorporating puns and wordplay into your icebreakers, you can create a light-hearted and engaging start to your conversations, increasing the chances of building a connection with your match!

Questions with a Twist

Who doesn’t love a twist? Questions that veer from the beaten path are fun queries that break away from the usual small talk. These kinds of questions can lead to interesting (sometimes wild) convos and reveal different aspects of a person’s character.

  • “If you could have an unlimited supply of one thing for the rest of your life, what would it be?”
  • “What’s your weird hidden talent that no one knows about?”
  • “If you could be on any reality TV show, which one would you choose and why?”
  • “What’s the most unusual place you’ve ever visited, and what did you do there?”


Quirky questions are super effective in online dating for several reasons:

  • Revealing Personality: These questions allow people to share more about their personality, interests, and values in a fun yet indirect way. For instance, asking about a weird hidden talent can highlight someone’s creativity and sense of humor.
  • Starting Interesting Conversations: Such questions can shift conversations away from boring topics and into more engaging territory. They encourage storytelling and personal anecdotes, making the interaction dynamic and enjoyable.
  • Encouraging Openness: Answering unconventional questions can make people feel more comfortable and open, as they are often less intimidating than direct personal questions.
  • Showing Genuine Interest: Asking creative questions shows that you are actually interested in getting to know the other person and have put thought into your approach. This can be very appealing and set a good tone for the interaction.

Pop Culture References

Pop culture will never fail you in the icebreaker department—almost everyone is schooled in it, and it’s universal!

  • “Do you like Harry Potter? Because I a-Dumbledore you!”
  • “Are you a Hogwarts letter? Because you’ve been waiting for me.”
  • “Do you like Star Wars? Because Yoda one for me.”
  • “Do you like The Office? Because I think we could be Jim and Pam.”


Referencing popular movies, shows, or memes in your icebreakers is always a solid strategy!

  • Creating Common Ground: When you use well-known references, you instantly create a sense of familiarity. If the other person recognizes the reference, it can lead to an immediate connection and something to bond over and chat about.
  • Showing Personality: Pop culture references do double duty by letting you show your interests and sense of humor. If you both like the same shows or movies, it indicates that you might have similar tastes and hobbies, which can be a great conversation starter.
  • Adding Humor: References to popular culture often come with a humorous twist, making the interaction more light-hearted and enjoyable. This can help ease any initial awkwardness and make the conversation flow more naturally.
  • Encouraging Engagement: Using a reference can prompt the other person to respond with their own thoughts or related jokes, keeping the conversation interactive and fun. It can also reveal common interests, making it easier to find more topics to talk about in the future.

Compliment Jokes

Combining humor with flattery is a great way to make a positive impression in online dating. Compliment jokes not only make the other person feel good but also add a flirty vibe to the conversation.

  • “Is your name Google? Because you have everything I’ve been searching for.”
  • “Are you French? Because Eiffel for you.”
  • “If beauty were time, you’d be an eternity.”
  • “Is your dad a boxer? Because you’re a knockout!”


Blending flattery with humor can make a strong impact for the following reasons:

  • Boosting Confidence: Compliments make people feel good about themselves, boosting their confidence and making them more likely to engage positively with you. When delivered with humor, it can lighten the mood and make the compliment even more impactful.
  • Demonstrating Creativity: Compliment jokes show that you are creative and can think outside the box. This can be very appealing and makes you stand out from the generic approaches.
  • Creating a Relaxed Atmosphere: Humor goes a long way in breaking the ice and creating a chill atmosphere, making the other person feel more comfortable and open to talking. A well-timed joke can turn a potentially weird situation into a fun interaction.
  • Making a Lasting Impression: A compliment that also makes someone laugh is more likely to be remembered. It shows that you not only noticed something special about them but also took the time to write a thoughtful and humorous message.

Situational Humor

Situational humor involves creating fun and hypothetical scenarios to start interesting conversations. This approach is a great way to connect with someone and show off your creativity.

  • “If we were both characters in a horror movie, what would our storyline be and would we survive?”
  • “If we could switch lives for a day, what’s the first thing you would do as me?”
  • “Imagine we’re stranded on a deserted island. What’s the one item you’d want to have with you?”
  • “If we had a time machine, which historical event would you want to visit together and why?”


Using hypothetical scenarios can make conversations so much more fun—here’s why:

  • Stimulating Creativity: Hypothetical questions encourage both parties to use their imagination, leading to more interesting and spontaneous conversations.
  • Revealing Personality: These scenarios can uncover better insights into someone’s personality, preferences, and sense of humor. For example, discussing how you’d survive a horror movie can tell you how someone handles stress or approaches problem-solving.
  • Creating Engagement: Hypothetical scenarios can lead to a back-and-forth exchange of ideas, making the conversation more dynamic. This helps build a connection as both parties contribute to crafting the story or scenario.
  • Adding Fun and Playfulness: These questions introduce an element of fun and playfulness, making the interaction more relaxed.

Crafting Your Own Hilarious Icebreakers

Creating your own icebreakers for online dating can be a fun and rewarding process, as it allows you to show off your personality, humor, and creativity! Here are some tips so you can craft your own hilarious icebreakers!

Know Your Audience

Tailoring your humor to the person’s profile and interests is important, so pay close attention to the details they provide, like their hobbies, favorite movies, or music. This not only shows that you’re genuinely interested but also helps you write a more personalized and relevant icebreaker. For example, if someone mentions loving sci-fi movies, you might say, “If we were in a Star Wars movie, would you be my Jedi partner?” This kind of approach can make your message more appealing to the reader and is likely to get a response.

Keep It Light and Positive

Always, always, always avoid humor that could be in any way misinterpreted or offensive. Yes, it’s important to be funny, but it’s just as important to be considerate and respectful. Stay well clear of controversial or sensitive topics. Instead, use humor that is lighthearted and universally relatable. A simple, playful joke can go a long way. For instance, “Do you believe in love at first swipe?” keeps things fun without crossing any lines.

Man Crafting Funny Ideas to Attract Partner

Be Real

Staying true to your personality and sense of humor is key—being yourself resonates well with people. If you’re naturally sarcastic, let that show in a way that’s endearing rather than harsh or nasty. Conversely, if you’re more straightforward, a simple and honest joke or playful comment will feel more genuine. Something along the lines of, “I’m new here, can you show me around?” can be both cute and true to who you are.

Practice Makes Perfect

Trying out different icebreakers and learning from responses is a great way to hone your approach. Don’t be discouraged if your first attempts don’t get the response you hoped for. Experiment with different styles of humor and pay attention to what works best. Over time, you’ll get a better sense of what works well with your matches. Consider keeping a few go-to lines handy and rotate them to see which ones get the best reactions. Try out “What’s the most unexpected thing that happened to you today?”—it can be a great conversation starter!

Real-Life Examples and Success Stories

Dating is hard, so finding what you consider “success” on dating apps can sometimes feel like a losing battle—but a well-times funny icebreaker can turn the tide in your favor! It can change a random match into a meaningful connection. We want to highlight some IRL stories that show how humor can be the exact answer to kicking off conversations and building romantic relationships. But first, here are some user-submitted icebreakers that we think will work wonders!

User-Submitted Icebreakers

  • “Would you rather always be a little bit damp or a little bit sticky?” This is an excellent quandary that we don’t have an answer to—both sound terrible. But it’s a thinker and that gets a response!
  • “What’s the most unusual place you’ve ever visited?” This icebreaker can lead to crazy stories and highlight the more adventurous side of matches.
  • “If you were an ice cream flavor, which one would you be and why?” This sweet, cutie-pie question prompts a fun and imaginative discussion.
  • “What’s your worst travel story?” Sharing travel mishaps can create a bond over common experiences and funny misadventures.
  • “What’s an odd habit you fall into when you get stressed out?” This question mixes light-heartedness with genuine curiosity about the other person’s coping mechanisms.
  • “What’s the most embarrassing thing you’ve ever done in public?” This question encourages vulnerability and self-disclosure, making the convo more personal and engaging—not to mention funny.
  • “If you could buy anything this year (money is no object), what would it be?” This open-ended question can tell you about someone’s personal interests and goals.
  • “How are we doing tonight? Have you dined with us before? Let me know if you have any questions about the menu.” 10/10, chef’s kiss, no notes.
  • “Who’s your celebrity crush, and why is it Rhianna?” Everyone loves Rihanna, so this is an easy one. It also gives them the chance to say someone else, but beware, most people will go to great lengths to defend their RiRi crush!

Success Stories

And now for the success stories that went from an icebreaker on a dating app to real-life romance!

How a Shared LOL Led to a First Date

Emily and Josh matched on the dating app Bumble. Emily broke the ice with the question, “If you could have any superpower, what would it be and why?” Josh’s response set the tone for a conversation filled with humor and common interests—they spent hours chatting online, discovering a mutual love for superheroes and fantasy worlds.

This initial fun exchange led to their first date, which continued the fun and light-hearted theme. They enjoyed a series of dates that involved watching superhero movies and even attended a comic-con together! Their romantic relationship blossomed from these first laughs, proving that a humorous icebreaker can indeed pave the way to a deeper connection.

Turning a Funny Conversation into a Long-Term Relationship

Savannah and Micka’s story started on OkCupid but took off on Tinder years later. Savannah’s icebreaker was, “What’s the most unusual place you’ve ever visited?” This question led to a lengthy conversation about their travel adventures and experiences. They found they had a lot in common, including a love for exploring new places and trying new things. Their conversations flowed naturally, filled with humor and intriguing stories, which helped them bond despite initially being long-distance.

Over time, their connection grew stronger, leading them to move in together and eventually get married. Their story shows how an engaging and funny conversation can turn into a lasting romantic relationship!

The Confidence Booster

Ok, so this one doesn’t lead to a long-term relationship, but we think it’s still important to share with our readers—sometimes, sending the initial message can help you build up your courage! “Stephanie wasn’t accustomed to sending the first message on dating apps. In fact, she’d been struggling with her confidence since she was a teenager,” she told Bumble.

“That changed when she decided to take control of her dating life and get on Bumble, where she had to approach men. It was scary at first, but she quickly found herself enjoying coming up with questions. It even became a new talent of hers. Before she knew it, she was making moves in all areas of life with courage she’d never felt before.”

Potential Pitfalls and How to Avoid Them

Using humor in online dating is a wonderful way to break the ice and build connections, but it also comes with some potential pitfalls! Knowing what they are and how to navigate them if they happen will help you use humor well—and in a respectful way.


Not everyone has the same sense of humor, which means it can be misunderstood or misinterpreted, especially in written form where tone, inflection, and facial expressions are absent. Sarcasm, in particular, is really easily misunderstood. If your humor doesn’t land like you intended, it’s important to handle the situation gracefully.

If someone seems confused or offended by your joke, immediately clarify your intent. You can say, “I was just trying to be funny, I’m so sorry if that didn’t come across well!” This shows that you are considerate and willing to acknowledge and own up to any possible misunderstandings on your end.

Timing and Context

Knowing when to use humor and when to switch gears to a more serious tone is also a must. Early interactions are best kept light and playful, but as the conversation progresses, it’s important to gauge the other person’s responses and adapt accordingly. If the chat turns to more serious topics, such as personal challenges or life philosophies, shifting your tone to express empathy and understanding is essential. Balancing humor with sincerity can build a better, stronger, and more genuine connection.

Respecting Boundaries

Respecting the other person’s comfort level and reactions is paramount to successful online dating. Not everyone appreciates the same type of humor, and what might be funny to one person could be offensive to another. Always start with light, inoffensive jokes and gradually move to more playful banter as you get to know the person better.

Pay attention to their reactions: if they seem uncomfortable or do not respond to your jokes, take the conversation in a different direction. Avoid humor that targets sensitive topics or could be seen as derogatory.

Navigating Humor in Online Dating

We all make goofs when trying to impress someone we are romantically interested in, but that doesn’t mean you have to bow out or hang your head in shame! Here are two stories of humor gone wrong that ended on a happy note.

Turning Misunderstanding into Connection

Jessica and Pedro met on Bumble, and their first few messages were filled with flirty banter. However, one of Jessica’s jokes didn’t land well, and Pedro seemed a bit put off. Jessica quickly apologized, clarifying that her goal was to be funny, not offensive. This simple act of empathy turned the situation around, and they ended up laughing about it. Their ability to navigate this early misunderstanding laid a strong foundation for their relationship, which eventually blossomed into a long-term romance!

Timing and Empathy Leading to a Stronger Bond

Kevin and Michaela’s journey started out with a humorous icebreaker on Bumble. She asked him, “If you could meet any person, living or dead, who would it be and why?” This question kicked off a fun conversation. As their chat progressed, the topics naturally turned to more serious matters like career aspirations and personal values. Michaela’s ability to go from playful banter to a sincere discussion showed Kevin that she was both fun and empathetic.

This balance of humor and seriousness strengthened their bond—they’re still together today. Oh, and his answer to her icebreaker? Amelia Earhart (he wants to know what happened on that flight).

Practical Tips for Using Humor in Online Dating

  • Start Light: Use simple, inoffensive jokes or questions to gauge the other person’s humor style. For example, “What’s your favorite way to unwind after a really stressful day?”
  • Observe Reactions: Pay attention to how the other person responds to your humor. Positive engagement is a green light to continue; hesitation or discomfort means you need to tone it down.
  • Be Ready to Apologize: If a joke doesn’t hit the mark, a simple and sincere apology can help clear the air and show that you value the other person’s feelings.
  • Mix Humor with Depth: As you get to know each other, blend your humor with deeper, more meaningful conversations to create a well-rounded connection.
  • Avoid Sensitive Topics: Stay away from jokes about race, religion, politics, or any other potentially sensitive subjects until you are sure of the other person’s boundaries and comfort level.

Additional Resources and Tips

If you’re looking for the perfect funny icebreaker, improving your conversational skills, or want some feedback on your approach, the following are some helpful resources and tips to level up your online dating experience!

Online Tools and Apps

There are some apps and websites designed to help you generate funny icebreakers for online dating, like the following:

AI (artificial intelligence) icebreaker generators:

Books and Articles

Improving your humor and conversation skills can be supported by further reading, so here are six recommended books and articles that we think will help:

  • The Humor Code” by Peter McGraw and Joel Warner: This book explores what makes things funny and how humor varies across different cultures. It’s a great read for understanding the mechanics behind humor.
  • Laughter: A Scientific Investigation” by Robert Provine: Provides insights into the science of laughter and its social significance, which can help you use humor more effectively in conversations.
  • How to Win Friends and Influence People” by Dale Carnegie: While not solely focused on humor, this iconic book offers valuable advice on building rapport and engaging people, including through the use of light-hearted conversation.
  • Comedy Writing Secrets” by Mark Shatz: This book offers practical tips on crafting jokes and using humor in writing and speaking, which can be directly applied to online dating interactions.
  • Humor, Seriously” by Jennifer Aaker and Naomi Bagdonas: Explores the power of humor in professional and personal settings, providing actionable tips to incorporate humor into your daily interactions.
  • Universal Class: Using Humor in Communications is an article that dissects how humor can improve communication in all areas of your life.
  • The Behavior Hub: Positive Communication: Try Some Humor explores the role humor has in communication.

Practice with Friends

Workshopping your icebreakers on friends before using them in online dating can give you invaluable feedback, too!

  • Gather Feedback: Share your icebreakers with friends and ask for their honest opinions. They can help you refine your jokes and make sure they come across as intended.
  • Role-Playing: Engage in mock conversations where you practice your icebreakers in different scenarios. This can help you become more comfortable and spontaneous when using them in real interactions.
  • Observe Reactions: Pay attention to your friends’ reactions. If something doesn’t get the response you hoped for, tweak it until it feels right. Friends can provide a safe, nonjudgmental space to experiment and improve your humor skills.

From LOLs to Love: Wrapping Up Our Icebreaker Adventure

Humorous icebreakers can work wonders in online dating—they lighten the mood and diffuse any awkwardness, making both people feel more comfy. They also show off your personality and create a fun, engaging vibe that encourages the other person to open up. A good laugh can turn a weird moment into a connection, making your conversation memorable for all the right reasons. So, don’t be scared to toss in a witty joke or a fun question—it could be the start of something special!

Humor does the heavy lifting by making things way less awkward in initial dating app messages—it just makes everything easier. A solid joke or an interesting question can turn a stiff start into a great connection—humor is your BFF in online dating, so use your buddy responsibly, and use it often!

We’d love to hear your favorite icebreakers—please tell us all of them in the comments! And feel free to use the ones we shared; give them a go and let us know how they worked!

Molly Davis
Molly Davis

Molly is an East Coast writer who lives on West Coast time. She’s been in the journalism field for over 20 years — newspapers are her first love but she’s finding digital media to be just as fun and challenging as print! When she’s not giving therapist-quality dating advice, she’s curled up watching movies, reading, or volunteering at local dog shelters.