You matched with someone great. Now what? If you're staring at your screen wondering what to say, you're not alone. The first message can feel impossibly high-stakes—but it doesn't have to be. This guide gives you 50+ proven conversation starters that go way beyond "Hey" and actually lead to real conversations.
Why Your First Message Matters
more responses with personalized openers vs. "Hey"
of "Hey" messages go unanswered
sentences is the ideal message length
Why "Hey" Doesn't Work (And What Does)
Let's address the elephant in the room: "Hey" almost never works. Here's why:
- Zero effort shown — It signals you couldn't be bothered to think of something real
- Nothing to respond to — The other person has to do all the work
- Gets buried — It looks identical to dozens of other messages they receive
- No personality — Tells them absolutely nothing about who you are
What does work? Messages that:
- Reference their profile — Show you actually looked at it
- Ask open-ended questions — Give them something easy to respond to
- Show genuine curiosity — Not just compliments, but real interest
- Have personality — Let your authentic self come through
Profile-Based Conversation Starters
The best openers reference something specific from their profile. Here are templates you can adapt:
For Travel Photos/Mentions
"That photo in [place] is amazing! What was the highlight of that trip?"
"I've always wanted to visit [place]—would you recommend it? Any must-see spots?"
"Okay I need details on that [place] trip. Best food you had there?"
For Hobbies & Interests
"I see you're into [hobby]! How did you get started with that?"
"Fellow [hobby] person here! What's your favorite [related thing]?"
"I've been wanting to try [their hobby]. Any tips for a complete beginner?"
For Food & Cooking
"I noticed you love [cuisine]. Do you have a go-to restaurant or do you cook it yourself?"
"Serious question: what's your controversial food opinion?"
"If you could only eat one cuisine for the rest of your life, what would it be?"
For Pet Photos
"Okay, I have to know—what's [pet's name]'s personality like?"
"Your [pet] is adorable! How did you two meet? (Is that weird to ask? I'm asking anyway.)"
"I'm going to need more photos of your [pet]. For research purposes."
Fun "Would You Rather" Questions
These work great when their profile doesn't give you much to work with, or you want something playful:
"Would you rather have the ability to fly or be invisible?"
"Would you rather only be able to whisper or only be able to shout?"
"Would you rather give up coffee or give up your phone for a month?"
"Would you rather have a personal chef or a personal driver?"
"Would you rather live in a treehouse or a houseboat?"
"Would you rather know all languages or talk to animals?"
"This or That" Quick Questions
Simple, low-pressure, and easy to answer—great for sparking quick back-and-forth:
"Coffee or tea?"
"Beach vacation or mountain getaway?"
"Morning person or night owl?"
"Sweet or savory breakfast?"
"Books or podcasts?"
"Cook at home or eat out?"
"Plan everything or be spontaneous?"
"Cats or dogs?" (Classic for a reason)
Deeper Conversation Starters
Once you've established some rapport, or if their profile suggests they want deeper conversation:
"What's something you've changed your mind about in the last few years?"
"What's the best piece of advice you've ever received?"
"If you could master any skill overnight, what would you choose?"
"What's something you're looking forward to right now?"
"What does your perfect Sunday look like?"
"What's the last thing that made you genuinely laugh?"
Funny/Quirky Openers
If their profile has humor, match that energy:
"On a scale of 1 to 'I have strong opinions,' how do you feel about pineapple on pizza?"
"I'm conducting important research: what's the correct way to load a dishwasher?"
"Quick—you have to pick a theme song that plays every time you enter a room. What is it?"
"I'm trusting you with an important decision: what snack should I get from the store right now?"
"What's the weirdest Wikipedia rabbit hole you've gone down?"
What NOT to Do: First Message Red Flags
Avoid These Common Mistakes
- ✗ "Hey" / "Hi" / "What's up" — Zero effort, gets ignored
- ✗ Physical compliments only — "You're hot" or "You're beautiful" doesn't start conversation
- ✗ Copy-paste generic messages — People can tell when it's not personalized
- ✗ Overly long essays — 3 paragraphs as a first message is overwhelming
- ✗ Interview-style questions — "Where are you from? What do you do?" feels like a job interview
- ✗ Sexual comments — Unless their profile explicitly welcomes it, don't
- ✗ Negging or backhanded compliments — This isn't 2010, and it never actually worked
Pro Tips for Better Conversations
Be Specific
"I love that photo in what looks like Italy" is better than "Nice photos!" Specificity shows you paid attention.
Ask Open-Ended Questions
Questions that can't be answered with just "yes" or "no" keep conversation flowing naturally.
Show Your Personality
Don't be afraid to be a little weird, funny, or different. Generic = forgettable. Authentic = memorable.
Match Their Energy
If their profile is playful, be playful. If it's thoughtful, ask deeper questions. Mirror their communication style.
Don't Overthink It
A good-enough message sent beats a perfect message never sent. Just be genuine and interested.
Frequently Asked Questions
What is the best first message to send on a dating app?
The best first message references something specific from their profile and asks an open-ended question. For example: "I noticed you love hiking—what's the most memorable trail you've done?" This shows you read their profile, demonstrates genuine interest, and gives them an easy way to respond.
Why does "Hey" never work?
"Hey" fails because it requires the other person to do all the work. It shows zero effort, demonstrates you didn't read their profile, gives them nothing to respond to, and looks identical to dozens of other messages they receive. Studies show personalized openers get 3x more responses.
How long should my first message be?
1-3 sentences is ideal. Long enough to show thought and personality and give them something to respond to, but short enough not to overwhelm. Multi-paragraph first messages can feel like too much too soon, while single-word messages show no effort.
What if their profile doesn't give me anything to work with?
Use a fun hypothetical question, "would you rather," or "this or that" question. These work for any profile and can reveal personality. If they have photos, you can often comment on the setting, activity, or vibe even if their bio is empty.
Start Conversations That Matter
The best conversations start with genuine curiosity. Don't stress about finding the "perfect" opener—focus on being authentic, showing you read their profile, and giving them something interesting to respond to.
Remember: the goal isn't to impress them with a clever line. It's to start a real conversation with a real person. Be yourself, be curious, and don't be afraid to be a little different.
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