To start a conversation on a dating app, fun and funny conversation starters are playful, personalized opening messages designed to break the ice and increase reply rates. Instead of generic greetings like “Hey,” they use humor, shared interests, or profile-based questions to spark curiosity, show personality, and make conversations feel more natural from the first message.
Are you tired of sending the same old “Hey, how’s it going?” message on dating apps? Do you want to stand out and make a memorable first impression? Starting a conversation on a dating app can be nerve-wracking, but it doesn’t have to be boring. In this blog post, we will explore fun and funny ways to start a conversation on a dating app that will catch your match’s attention and hopefully lead to a great conversation.
Why the First Message Matters on Dating Apps
Hullo is an AI-powered dating app designed to help people connect more naturally and authentically. By analyzing behavior, interests, communication style, zodiac signs, and location, Hullo helps users find more compatible matches and start conversations that feel genuine instead of forced. With features like First Voice and AI Bio Generator, Hullo supports meaningful connections beyond surface-level swiping.
On dating apps, the first message often decides everything.
A generic opener like “Hey” or “Hi” may feel safe, but it rarely sparks curiosity or emotion. Many users receive dozens of similar messages, which means yours can easily get lost. This is exactly why understanding why “Hey” doesn’t work on dating apps anymore is crucial before sending your first message.
A thoughtful or funny conversation starter shows:
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Effort and intention
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A glimpse of your personality
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Genuine interest in the other person
When the first message feels human and specific, the conversation has a much better chance of continuing.
Looking to practice better first messages with compatible matches? This is where AI-driven dating apps like Hullo help create more natural conversation flow: hullo.dating
How to Start a Conversation on a Dating App Reddit
Reddit is a popular platform for discussions and advice, and it’s no surprise that there are many threads dedicated to starting conversations on dating apps. Many of the most upvoted answers align with guides on how to start a conversation on a dating app without being awkward.
Be Genuine and Personal
One of the most common pieces of advice from Reddit users is to actually read the other person’s profile.
Instead of commenting on looks alone, find something specific:
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A hobby
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A favorite movie or show
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A travel photo
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A quirky prompt answer
For example, if they mention loving hiking, you could ask about their favorite trail or share a funny hiking mishap of your own.
Why it works:
Personal messages feel intentional and show you’re interested in who they are, not just matching randomly.
Use Humor (But Keep It Light)
Humor is a powerful icebreaker. A funny opening message can instantly lower tension and make someone feel comfortable replying.
That said, Reddit users also warn against:
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Offensive jokes
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Sexual humor too early
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Trying too hard to be edgy
Light, playful humor works best, especially when it connects to the profile. Many successful examples can be found in collections of funny dating app openers that actually get replies.
How Do I Start a Conversation on a Dating App?
If you’re new to online dating, you may be wondering how to start a conversation on a dating app. Here are some general principles that also appear in guides on how to start a conversation on a dating app without being awkward.
Ask Open-Ended Questions
Asking open-ended questions is a great way to keep the conversation flowing and get to know your match better. Instead of asking yes or no questions, try to ask questions that require more than a one-word answer. This will show your match that you’re genuinely interested in getting to know them and can lead to more meaningful conversations.
Be Creative with Your Opening Line
Instead of using the same old “Hey” or “What’s up?”, try something unique. Creative openers show personality and set the tone early. Many of these ideas overlap with creative conversation starters based on dating profiles, which tend to get higher response rates.
Fun Ways to Start a Conversation on a Dating App
Now that we’ve covered some general tips, let’s dive into some fun ways to start a conversation on a dating app:
Use a GIF or Meme
GIFs and memes are popular ways to communicate on social media, and they can also be used to start a conversation on a dating app. Find a funny or relatable GIF or meme that relates to something on your match’s profile and send it as your opening message. This can break the ice and make your match laugh, making them more likely to respond.
Play a Game
Simple games like “Would You Rather?” or guessing a favorite movie turn chatting into a shared activity. These techniques are often used in creative conversation starters based on dating profiles because they feel interactive instead of forced.
Send a Funny Pickup Line
Funny pickup lines can work when they’re self-aware and lighthearted. Many examples that succeed fall under funny dating app openers that actually get replies, especially when they’re personalized.
Funny Ways to Start a Conversation on a Dating App
If you have a good sense of humor, why not use it to start a conversation on a dating app? Here are some funny ways to start a conversation that will make your match laugh:
Use Puns
Puns are a great way to show off your wit and make someone laugh. You could use a pun related to their name or interests, or even a cheesy pickup line turned into a pun. Just make sure not to overdo it, as too many puns can become tiresome.
Make a Joke About Yourself
Self-deprecating humor can be endearing and relatable. You could make a joke about yourself or share a funny story from your own experiences. This can show your match that you don’t take yourself too seriously and can make them feel more comfortable opening up to you.
Everyone loves a good story, especially if it’s funny. Think of a funny anecdote from your life and share it with your match. This can spark a conversation and give you both something to laugh about.
How to Start a Conversation on a Dating Site Examples
Here are some examples inspired by everything above:
- “I couldn’t help but notice your love for hiking. What’s your favorite hiking spot?”
- “I have a feeling we’re going to get along just fine. We both love pizza and The Office.”
- “I have a confession… I’ve never seen Game of Thrones. Should I start?”
- “I’m terrible at pickup lines, but are you a bank loan? Because you have my interest.”
- “I’m convinced your profile was written by a psychic.”
These examples avoid common traps covered in first message mistakes that kill dating app conversations.
What is a Good Way to Start a Conversation on a Dating App?
Ultimately, the best way to start a conversation on a dating app is to be yourself and show genuine interest in the other person. However, here are some general tips for starting a good conversation:
- Keep it light and fun
- Avoid controversial topics or anything too personal
- Use proper grammar and spelling
- Don’t send multiple messages if your match doesn’t respond right away
- Be respectful and considerate of the other person’s boundaries
Want to improve your profile so starting conversations feels easier? Try the Hullo AI Bio Generator to craft a bio that sparks better openers: hullo.dating/ai-bio-generator
How to Start a Dating Conversation and Keep It Going
Starting a conversation on a dating app is just the first step. To keep the conversation going and build a connection with your match, here are some tips on how to start a dating conversation:
Ask Follow-Up Questions
Asking follow-up questions shows that you’re actively listening and interested in what the other person has to say. This can also lead to more in-depth conversations and help you get to know each other better.
Sharing personal stories can make the conversation more meaningful and help you connect with your match on a deeper level. Just make sure to keep it appropriate and avoid oversharing.
Be Yourself
It’s important to be yourself and not try to be someone you’re not. This will only lead to disappointment in the long run. Show off your unique personality and let your match get to know the real you.
To learn how to stay safe while building meaningful connections, explore Hullo’s guide on Internet Dating Safety Tips to protect yourself while dating online.
Starting a conversation on a dating app doesn’t have to be boring or nerve-wracking. By using these fun and funny ways to start a conversation, you can make a memorable first impression and hopefully spark a great conversation. Remember to be genuine, use humor, and be yourself, and you’ll be on your way to finding a meaningful connection on a dating app.
PEOPLE ALSO ASK
1. What is a good first message on a dating app?
A good first message is personalized, light, and based on the other person’s profile, using open-ended questions or humor instead of generic greetings.
2. Do funny conversation starters get more replies?
Yes. Funny conversation starters help reduce awkwardness, show personality, and often lead to higher reply rates when the humor feels natural and relevant.
3. How does Hullo help people start better dating conversations?
Hullo uses AI to match users based on behavior, interests, and communication style, making it easier to start conversations that feel natural and aligned from the first message.
