5 Creative Questions to Spark Conversation on a Dating Site

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In 2023, more than 381 million people worldwide used online dating services. Which means that when it comes to sending a message, you really are up against some serious competition! If you want to stand out from the crowd, you’ll have to do better than “hey”. So once someone has piqued  your interest on OBC, why not kick things off with something a bit more creative? Here are five fun questions you can ask to break the ice and get the conversation flowing:

  1. If you could have dinner with any fictional character, who would it be and why?

    • This question opens the door to talk about favorite books, movies, or TV shows, and gives insight into their imagination. Or, if you’re a history buff, ask them who from the past they’d like to chat up!

  2. What’s your go-to karaoke song, and how seriously do you take it?

    • Whether they’re a karaoke pro or a reluctant singer, this question can lead to some funny or surprising stories. Bonus points if you make them prove it with a date to a karaoke bar! 

  3. If you could only eat one type of cuisine for the rest of your life, what would it be?

    • Food is always a great topic, and this question lets you explore their tastes and maybe even plan a future date at their favorite restaurant. 

  4. What’s the most spontaneous or scary thing you’ve ever done?

    • This question encourages sharing adventurous or bold moments, which can be a great way to connect over a love of spontaneity and making daring choices! 

  5. If you could instantly become an expert in any hobby or skill, what would you choose?

    • This is a fun way to learn about their interests or dreams, and it might even spark a conversation about trying new activities together. To get some laughter going, ask which skill they’re actually TERRIBLE at (cooking, skateboarding, and anything related to math?!).

Using these questions, you can start a conversation that’s engaging and memorable, helping you both discover if there’s a spark worth exploring — then get in some face time with an IRL date to keep the conversation going.

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