Starting a conversation with your crush can feel like walking a tightrope—you want to impress them, keep things light, and still show genuine interest. The key? Ask unique and thoughtful questions that move beyond the typical “How was your day?” or “What kind of music do you like?”

Whether you’re texting, hanging out in person, or chatting over the phone, the right questions can spark laughter, curiosity, and maybe even a little flirtation. Here are some one-of-a-kind questions to help you connect on a deeper level—and keep the conversation going strong.

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

This opens the door to talk about books, movies, or shows they love—and why. You’ll learn who inspires or entertains them and maybe get a fun recommendation out of it too.

2. What’s the most unexpected compliment you’ve ever received?

This question is a sneaky way to find out what others notice about them—and what they think is memorable or surprising about themselves.

3. What’s something totally normal that you find fascinating?

From watching clouds to organizing playlists, everyone has little quirks. This can turn into a surprisingly deep or funny conversation.

4. What’s a skill you’ve always wanted to learn but never tried?

You’ll get insight into their interests or dreams—and possibly find something you could try learning together.

5. What’s your favorite way to spend a lazy weekend?

This one helps you imagine how your lifestyles might mesh and shows what they value in their downtime.

Right in the middle of a fun conversation, it’s the perfect time to throw in some of the best would you rather questions. These kinds of questions are playful, unexpected, and revealing. Whether it's choosing between living in space or underwater, or deciding whether they’d give up social media or dessert forever, “would you rather” games bring out their spontaneity, sense of humor, and decision-making style—all while keeping things light and engaging.

6. What’s the most spontaneous thing you’ve done in the past year?

If they’re adventurous, you’ll hear about fun road trips or impulsive plans. If not, it’s still a window into their comfort zone and lifestyle.

7. If your life had a theme song, what would it be?

Music is a great way to connect emotionally. Their answer will likely be personal—and you might find a new favorite track too.

8. What’s something that instantly makes you smile?

A sweet question like this is perfect if you’re trying to be a little flirty and thoughtful at the same time.

9. What’s a moment in your life you’d love to relive?

This opens the door to nostalgia and meaningful memories—and shows what truly matters to them.

10. If you could master one random talent overnight, what would it be?

A fun and imaginative way to end the chat, this helps you learn what excites or intrigues them.

Next time you’re talking to your crush, try mixing in these creative questions—you might be surprised how quickly the connection grows.