Dating Dating & Love

These Playful Conversation Starters For Dating Are Actually Interesting (We Swear)

What are you an armchair expert on?

Dating apps make it possible to meet dozens of potential partners a day (or hundreds, if you don’t have a job). Chatting with that many strangers gets old quick without some unique and fun conversation starters for dating in your back pocket.

Sure, you can always default to a simple “hey!” But we prefer to make things more interesting. Especially for those folks with prompt-less Hinge profiles that give you nothing to work with.

Whether you’re more of a Tinder girlie or a Bumble babe, we’ve put together a list of conversation starters to help you stand out from the crowd.

25 Playful Conversation Starters for Dating Apps

1. What’s the most embarrassing aspect of your Spotify Wrapped?

Is it their top artist? Genre? The amount of times they listened to Party in the USA? Obviously that last one is so not embarrassing, but you get the gist.

2. Wrong answers only: best place in [insert your city] for a date.

This dating conversation starter provides an easy way for them to propose taking you out at *not* that spot…or maybe you do go there for the laughs. Who doesn’t love memorable night at Chuck E. Cheese?

3. Which would you rather have: a beach house, lake house or mountain house?

Learn where their hobbies and interests lie, and begin envisioning your future vacation home. You two would really stand out in a beachfront mansion.

4. What’s the worst travel experience you’ve ever had?

Asking about their best travel experience works too, but worst is probably funnier. Give them a chance to open up about their awful snorkeling trip to Panama City, Florida. Dolphins are such pervs.

5. Would you rather only eat pizza for a year or not eat pizza for 5 years?

Woof… let’s hope they don’t turn this question back to you.

Conversation Starters for Dating - couple eating pizza

6. If you could relive one vacation, where would it be and why?

A fresh take on a cliché question. Because you’re above clichés.

7. Settle a debate. Does [insert local spot] have the best pizza or does [insert local spot]?

Feel free to substitute with ice cream, tacos, beer, coffee…basically, wherever you want to hint at for your next date.

8. Two truths and a lie. You start.

A quick way to learn a lot. Except whether they’re a pathological liar or not.

9. What’s a really popular food that you hate?

The best conversation starters for dating apps are the ones that provide on opportunity for teasing. Make fun of them for being the only person alive to hate ice cream. Who hurt you?

10. F*ck, Marry, Kill – [insert topic of choice]

Think: condiments, local restaurants, drinks. Obviously we’d get down with an espresso martini, marry the margarita and kill LITs. You can only withstand getting burned so many times.

Conversation Starters for Dating - espresso martinis

11. What’s the worst common wedding reception song?

Sorry, Walk the Moon, but we never want to hear “Shut Up and Dance with Me” again. Wave the green flags if they agree.

12. Who would play you in a movie?

Jonah Hill, you say? Circa Superbad or Stutz?

13. If you were DJ-ing right now, what song would you put on next?

Sing to me, Paolo. Or, you know, don’t.

14. If you had to, which reality TV show would you go on?

We’ll pass on anyone who willingly signs up for F*ckboy Island. Great British Bake Off? Now we’re intrigued.

15. How did you know I like [insert quality]?

Finish the sentence based on their dating profile. Snowboarders, German Shepherd-lovers, taco aficionados. Men with beards. Swoon.

Conversation Starters for Dating - man with beard

16. Give me your worst pickup line.

If you were a triangle, you’d be acute one. Or something about angels and falling.

17. Would you rather travel back in time or into the future?

Bonus points if they can pick a specific historical era to visit. We’re hot for historians.

18. If you could host dinner for a TV show cast, which would you choose?

If it’s not the cast of The Office, we need to have a serious conversation about whether this is going to work.

19. If you could only eat one thing for the rest of your life, what would it be?

Nobody wants to think about this question, but it does open up a lively discussion. You’d give up candy? For hot dogs?!

20. So, where are we going on our first date?

Cut right to the chase. Fortune favors the bold, baby.

Conversation Starters for Dating - woman swiping on dating app

21. How would you spend a billion dollars if you won the lottery?

This question tells you everything: what they value, how they manage and view money, and if they’re generous. It might just be a winning question (pun intended).

22. My friends and I are taking a poll. What’s a worse infestation to have in your apartment – mice or roaches?

And if that is too gross to ponder, take it down a notch with a poll like “what is the right way for a dog to wear pants?” We’re super passionate about that one, too.

23. Where do you land on the “is cereal a soup” debate?

Consider this the less basic version of “does pineapple belong on pizza?” And, “are hot dogs sandwiches?”

24. What’s better: TV shows or movies?

Would they rather spend a rainy day watching a bunch of classics or binge-watching Gilmore Girls? What? A girl can dream.

25. What are you an armchair expert on?

Another version of this question: what’s a topic you could give an hour long presentation on, no prep allowed?

By Jess Lohr

Jess is the co-founder of Adultescence, a podcast, blog and social media brand for twenty-somethings making the transition from life in college to adulthood. She writes about dating, friendship, money, and career. She also specializes in consumer insights, and is passionate about helping brands infuse the voice of their customers into their marketing, product, and CX strategies.

In her free time, you can find Jess spinning at The Handle Bar, obsessively consuming personal finance content, and playing with her adorable (but chaotic) puppy, Luca. You can follow her on Instagram @jesslohr or on LinkedIn.

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