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  • Jordan Wood

15 Questions To Ask On a First Date That Will Break Any Lull in the Conversation

Have you ever been on a first date and there’s that awkward lull where the two of you are trying to figure out what to say next? Yup. Me too. In fact, everyone has at least once. Well, don’t worry, I’ve got you covered with 15 conversation starters for a first date.

1. What would your friends say is your most embarrassing moment? This one will definitely get some laughs going. It loosens up the mood and puts a playful twist on the night. Plus, an embarrassing moment really yields a lot of information about the person. Was it a fart moment? Falling on their face? Something they said? You can find out what embarrasses them, what’s a potentially sensitive topic and if they hold on to things a little too long or just let it go and laugh it off.

2. What really bugs you that doesn’t bother most people? I’ve found out so many weird and wonderful things about a person with this question. Whether it’s people touching your toothbrush or nails dragging across fabric, there’s always something that bugs a person that doesn’t bother the majority of people.

3. What is the most annoying habit someone can have? This one goes hand in hand with question number two. With just these two questions, you can find out all sorts of wonderful quirks about the other person.

4. What did you used to love doing as a child? So often we lose touch with our childhood passions and talking about them reignites a spark within people. When someone talks about something they were/are passionate about with you, they can also subconsciously associate that warm and fuzzy moment with you. Whether this is true or not, if you’re into someone, it always helps to up your game any way you can.

5. Why did you stop doing this thing? As a follow-up to number four, find out why they stopped doing their passion. Was it time, money or maturity that made them no longer pursue their passion?

6. What is your perfect weekend? This question tells you if someone prefers lazy weekends around the house or being out and about the entire time. Are they a go-getter? Introvert? Extrovert? This simple question yields a glimpse into who the person is.

7. What’s your favourite place in the world? This shows what they’re sentimental about. Do they respond with a city or country or do they say something along the lines of their parent’s home or a childhood memory?

8. What is the biggest thing you’re proud of? What they respond could really surprise you. Some people that you expect to respond with some great accomplishment could say something very simple or vice versa. If they have no response, not even that eighth grade trophy, well, you might want to look elsewhere.

9. What inspires you? This could lead off onto a tangent of inspired dialogue or, it could fall flat on it’s face.

10. Who do you most admire? If question number nine went off well, try giving this question a try.

11. What’s on your bucket list? I love this question. I’ve found so many things in common that I never knew about when I’ve asked this question.

12. If you could be anyone else in the world, living or dead, who would it be? This question can reflect what some hidden life goals might be.

13. If you knew you just had a day to live, what would you do? Their response often reflects what is most important to them.

14. What was your favourite year and why? This one is a really different question but it can reveal a lot. Are they yearning for a time that they never even lived in or would they like to relive a certain magical year? This is conversation starter that could keep you talking for a while.

15. If you could go back in time, what would be the one piece of advice that you’d tell your younger self? I love this question. It often gets me thinking about their response and if it’s something I should take to heart myself.

While I wouldn’t fire all these questions at a person in one go, two questions from the list should spark some great conversation between you and your date. Good luck!

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