How To Start A Conversation On Dating App

So, picture this: I’m scrolling through a dating app, probably on a Tuesday night, fueled by questionable life choices and maybe a lukewarm cup of tea. My thumb is a blur, swiping left on blurry selfies and bios that read like a hostage negotiation. Then, BAM. A profile pops up. Interesting photos, a bio that’s actually witty and doesn't just list their favorite color. My brain, which had been operating at approximately 3% capacity, suddenly sparks to life. "Okay," I think, "this one’s a possibility." But then… the dreaded silence. The match appears, a little notification dinging like a tiny bell of impending doom. And I’m left staring at their profile, my mind a vast, echoing chamber. What do I even say? Do I go with a classic "Hey"? A bold "What's up?" Or do I unleash a painstakingly crafted opening line that’s probably destined for the digital abyss? It’s a familiar dance, isn't it? That moment of hopeful anticipation followed by the crippling fear of the blank message box.
This, my friends, is the existential crisis of the modern dater. We’ve mastered the art of the swipe, but the opening gambit? That’s a whole different beast. And let’s be honest, it’s often the make-or-break. A killer opener can launch you into a hilarious chat, maybe even a date. A dud? Well, you’re back to swiping, wondering if that person ever even saw your message. It’s a high-stakes game, played out in tiny text bubbles and emojis. But fear not, fellow warriors of the swipe! Today, we’re diving deep into the murky waters of dating app conversations. We’re going to arm you with the tools to ditch the boring greetings and actually connect with people. Think of this as your personal survival guide to actually getting a reply.
The "Hey" is Dead. Long Live the "Hey, Tell Me About Your Dog."
Let’s address the elephant in the digital room: the generic greeting. We’ve all sent them. We’ve all received them. The dreaded "Hey." It’s the conversational equivalent of beige. It’s safe, it’s easy, and it’s about as exciting as watching paint dry. Unless you’re a dog, in which case, "Hey" is probably a pretty good starting point. But for us humans, trying to forge a connection? We need a little more pizzazz. "Hey" doesn't tell me anything about you. It doesn’t spark curiosity. It just… exists. And then you’re left with the agonizing task of trying to salvage the conversation from the depths of blandness. It's like showing up to a party in a gray sweatsuit when everyone else is in sequins. You just don't stand out.
Think about it from their perspective. They’ve just matched with you. They’re scrolling through their messages, and what do they see? A wall of "Hey," "Hi," "What's up?" It’s overwhelming, and honestly, a little lazy. It suggests you haven’t put any effort in, and if you can’t even be bothered to craft a slightly more interesting opener, what does that say about your interest in them? Probably not much, right? So, the first rule of the dating app jungle: ditch the generic. Unless your profile picture is literally a puppy. Then, by all means, unleash the "Hey." But for everyone else, let’s elevate our game.
So, What Should You Say Instead? The Art of the Observational Opener.
This is where we get strategic. The absolute gold standard of dating app openers is the observational opener. What does this mean? It means you’ve actually looked at their profile. You’ve seen something that caught your eye, and you’re commenting on it. It’s like saying, "I see you. I’m interested in what you’ve put out there." This is crucial because it shows you’re not just spamming everyone. You’ve taken a moment to engage with them specifically.
Let’s break it down with some examples.
- Their Bio: Do they mention a love for hiking? A weirdly specific hobby? A funny quote?
- Their Photos: Are they in an exotic location? Posing with a hilarious prop? Wearing a truly questionable outfit (in a good way)?
Example 1: Let's say their bio says, "Seeking someone who can keep up with my questionable dance moves." Instead of a bland "Haha, I can dance," try: "Those questionable dance moves… are we talking dramatic interpretations of classic literature or more of a… enthusiastic flailing situation? Asking for a friend (who may or may not have two left feet)." See the difference? It’s playful, it’s specific, and it invites a response. You’re not just agreeing; you’re adding to the conversation.

Example 2: They have a photo of themselves at the top of a mountain. Instead of "Nice view," try: "That view looks incredible! Did you have to bribe a Sherpa to get you up there, or are you just naturally that athletic? Seriously though, what's your favorite hiking trail?" This shows you’re impressed, you’re curious about their adventure, and you’re asking an open-ended question.
Example 3: Their bio mentions they’re a huge fan of a niche band. Instead of "I like them too," try: "Okay, the fact that you’re into [Niche Band Name] is seriously impressive. What’s your favorite album? I’m still debating between [Album A] and [Album B] for the ultimate listening experience." This demonstrates shared interest and opens the door for a deeper discussion about their passions.
The key here is to be genuine and curious. Don’t force it. If you can’t find anything to comment on, then maybe they’re not the right fit, and that’s okay. But usually, there’s something. You just have to look a little closer. It’s like a treasure hunt, but the prize is potentially a date and maybe even a lifelong companion. Or, at the very least, a decent conversation that doesn’t make you want to delete the app.
The Power of the Question: Make Them Work for It (Just a Little).
Once you’ve made your initial observation, the next step is to keep the ball rolling. And how do you do that? By asking questions, of course! But not just any questions. We’re talking about open-ended questions. These are questions that can’t be answered with a simple "yes" or "no." They require a little more thought, a little more detail, and they’re the engine of any good conversation.
Think of it like this: if you ask "Are you busy this weekend?", the most likely answer is "No." End of conversation. BORING. But if you ask, "What’s your ideal way to spend a weekend when you’re not conquering mountains or dancing awkwardly?" Now they have to elaborate. They have to tell you about their dreams, their aspirations, their secret desire to become a professional cat cuddler. And that, my friends, is where the magic happens. You learn about their personality, their interests, their sense of humor.

Here are some question-based strategies:
- The "Two Truths and a Lie" Starter: This is a classic for a reason! You can say, "Okay, here’s my opener: I’ve been on a TV show, I can speak fluent Klingon, and I once accidentally joined a cult. Your turn! What are your three?" It’s fun, it’s interactive, and it immediately reveals something about them (and you!).
- The Hypothetical Fun: "If you could have any superpower, but it had to be something completely useless, what would it be?" Or, "If you could only eat one food for the rest of your life, but it had to be something you've never tried before, what would you choose?" These questions are low-pressure and often lead to hilarious answers.
- The "Dream Scenario": "If you won the lottery tomorrow, what's the first frivolous thing you’d buy?" Or, "If you could travel anywhere in the world for a week, no strings attached, where would you go and why?" These tap into their desires and aspirations.
The trick is to make the questions feel natural, not like an interrogation. Weave them into your observations. If you commented on their love for travel, ask about their favorite trip or their dream destination. If you noticed a quirky hobby, ask them how they got into it. Show genuine interest, and the questions will flow. And remember, it’s a two-way street. Be prepared to answer their questions too! Don’t be a conversational black hole.
Humor: The Universal Love Language (Especially on Dating Apps).
Let’s be real, dating apps can be exhausting. It’s a lot of pressure to be witty, charming, and endlessly interesting. But there’s one tool that can cut through the noise like a hot knife through butter: humor. A well-placed joke, a playful jab, or a self-deprecating remark can instantly make you more relatable and likable. It shows you don’t take yourself too seriously, and that’s a very attractive quality.
Now, humor is subjective, right? What one person finds hilarious, another might find cringeworthy. So, tread carefully. Avoid offensive or overly sarcastic humor, especially in the opening lines. You’re trying to build a connection, not start a roast. Think light, playful, and a little bit silly.
Humor in action:
- Self-deprecating charm: If their bio mentions they’re a great cook, you could say, "My cooking skills are so bad, I once set off the smoke alarm trying to boil water. I'm hoping you can be my culinary guru, or at least my emergency contact when the fire department arrives." It’s funny because it’s relatable (to some of us, anyway) and it’s not boasting.
- Playful teasing (gentle!): If they have a picture with a ridiculously large hat, you could say, "Is that hat designed to shield you from the sun, or is it actually a secret portal to another dimension? Because if it's the latter, I'm definitely intrigued." Keep it light and clearly a joke.
- Observational humor: Connect humor to something in their profile. If they mention a pet peeve, you can respond with a funny anecdote about your own version of that pet peeve.
The goal is to make them smile, to make them think, "Okay, this person is fun." Don’t try too hard to be a stand-up comedian. Just be yourself, and let your personality shine through. A genuine laugh is worth more than a thousand carefully crafted pick-up lines. It shows you’re human, and that’s what people are looking for. And hey, if your humor falls flat, at least you tried! That’s more than can be said for the person who just sent "hi."
Emoji Etiquette: The Silent Language of the Digital Age.
Ah, emojis. They’re the punctuation of the 21st century, and when used correctly, they can add a whole lot of personality and nuance to your messages. But when used incorrectly? Well, let’s just say it can be a minefield. Too many emojis, and you look like a teenager sending their first text message. Not enough, and your message might come across as flat or even a little cold. Emojis are like spices; use them judiciously.
When to deploy your emoji arsenal:
- To convey tone: A smiley face 🙂 can soften a potentially blunt statement. A winking face 😉 can add a playful or flirty undertone. A laughing face 😂 can emphasize that you found something genuinely funny.
- To add personality: If you’re talking about your dog, a dog emoji 🐶 is a no-brainer. If you’re expressing excitement about a potential date, a sparkle emoji ✨ or a celebratory emoji 🎉 can work wonders.
- To break up text: A well-placed emoji can add visual interest and make your message more digestible.
Things to avoid:
- The eggplant and peach: Unless you’re aiming for a very specific, very direct kind of interaction, these are best left out of the initial conversation. Trust me on this.
- Overload: Sending a wall of emojis is never a good look. It makes it hard to read and can come across as desperate or immature.
- Misinterpretation: Be aware that some emojis have different meanings in different cultures or contexts. When in doubt, stick to the universally understood ones.
Think of emojis as the little flourishes that enhance your message. They’re not a replacement for words, but they can definitely amplify them. Use them to add warmth, playfulness, and a touch of personality. A simple smiley face at the end of a funny anecdote can make all the difference. It’s like a little digital nod, saying, "I’m friendly and I’m enjoying this conversation."

When All Else Fails: The "Honest and a Little Vulnerable" Approach.
Look, sometimes, despite our best efforts, we still feel a little unsure. We’re human, and that’s okay. If you’re really struggling to find something witty or observational, there’s always the option of being just… real. A little bit of honesty and vulnerability can go a long way. It shows you’re not trying to be someone you’re not, and that’s incredibly refreshing.
This isn't about airing all your deepest insecurities, mind you. It’s about acknowledging the situation in a relatable way.
Examples of the "honest" opener:
- "Okay, confession time: I’m terrible at starting conversations on dating apps, so I’m going to lean on your amazing profile to get us going! What’s the most interesting thing you’ve done this week?"
- "My brain is currently running on fumes after a long day, but I’m genuinely intrigued by your profile. Tell me something that made you laugh today!"
- "Alright, I’m going to throw my hat in the ring. I saw your [specific detail from profile] and it made me smile. I’m usually much better at chatting in person, but here we are! How’s your evening going?"
The key here is to keep it light and positive. You’re not complaining; you’re being a little self-aware and inviting them to help bridge the gap. Vulnerability, when shared authentically, can be a powerful connector. It signals that you’re approachable and willing to be yourself. And honestly, who doesn’t appreciate a bit of honest effort? It’s far better than a ghosted "hey." So, don't be afraid to be a little imperfect. It’s often the most charming thing about us.
Ultimately, starting a conversation on a dating app is about more than just getting a reply. It’s about making a connection. It’s about showing a glimpse of who you are, and inviting them to do the same. So, ditch the bland greetings, be observant, ask questions, sprinkle in some humor, use emojis wisely, and when all else fails, be your wonderful, imperfect self. The digital world might be vast, but a genuine human connection can still shine through. Now go forth and conquer those message boxes!
