Better ways to start a conversation than "What’s up?"

Opening a conversation—especially on a dating app—can feel like trying to stand out in a crowded room. If your go-to line is “What’s up?” or simply “Hey,” you’re not alone—but you’re also not giving yourself the best chance. 

A great opener sets the tone, sparks curiosity, and makes it easy for someone to respond. And with Valentine’s Day around the corner, now’s the time to bring your A-game. Whether you’re looking for a flirty icebreaker, a way to stand out online, or just better conversation skills in general, these starters will get you past the small talk and into something worth discussing.

Ask something they actually want to answer

Instead of a generic “How’s your day?” ask something that makes them think. People love to talk about themselves, so give them a reason to share.

“What’s something you’ll never get tired of talking about?”
“If we were stuck in an elevator for an hour, what story would you tell me?”
“What’s one thing you’re irrationally passionate about?”

These questions invite someone to share something meaningful (or unexpectedly hilarious) while giving you an easy way to build on the conversation.

Playfully challenge them

A little friendly competition or a well-placed hot take can be the perfect spark for a fun conversation.

“Pineapple on pizza: Yes or no?”
“I bet I can guess your go-to coffee order. Want to test me?”
“What’s the best rom-com of all time?”

By setting up a playful challenge, you encourage engagement right away. And if they disagree? Even better—now you have something to debate.

Make it feel personal

People are more likely to respond when they feel like you’ve actually paid attention to their profile. Instead of a generic message, reference something specific.

“Your dog looks like they have major main character energy. What’s their name?”
“I see you love hiking. What’s the most breathtaking view you’ve seen?”
“Your playlist looks solid. What’s one song you’d put on repeat forever?”

Use humor to break the ice

A well-placed joke or funny question makes you instantly more memorable. People love to laugh, so even if they don’t have the perfect response, they’ll appreciate the creativity.

“Serious question: Would you rather fight 100 duck-sized horses or one horse-sized duck?”
“So, do we tell people we met online, or do we make up a ridiculous meet-cute story?”
“On a scale of 1 to ‘this is the most fun convo ever,’ how much are you enjoying this?”

Compliment in a way that isn’t boring

Flattery works, but only when it’s specific and genuine. Instead of “You’re cute,” try:

“That’s an A+ book collection. What’s the one you’d force me to read?”
“Your travel photos are next-level. Where should I book my next trip?”
“Your bio made me laugh. Do you write for fun, or are you just naturally hilarious?”

The common denominator? Make it about them.

How to actually keep the conversation going

A great opener gets your foot in the door, but keeping the momentum is what turns a match into a real connection. The best way? Be curious. Ask follow-up questions, share something about yourself, and avoid one-word answers. And if they mention something interesting, lean into it.

If you want to get even better at thinking on your feet and keeping conversations flowing, Elevate can help. The app sharpens your communication, quick thinking, and wordplay—so you’ll always have something great to say.