The 20 Absolute Best First Date Questions For Stimulating Conversation & Getting Deep


The 20 Absolute Best First Date Questions For Stimulating Conversation & Getting Deep


Naver Have An Awkward Silence On A First Date Again

The last thing you want on a first date is a long, uncomfortable silence. Whether this person is your soul mate or definitely not someone you'll be having a second date with, you still want to have a good time, get to know your date, and be a good conversationalist. Here are the 20 best first-date questions to help you do that. 

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1. What made you interested in me?

This one is a bit of a test for the other side. It will reveal if they actually read your profile or just looked at your photos. If you didn't meet online, it will reveal what stood out to them about you which will give you insight into what they value. 

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2. What's your go-to karaoke song?

This is a lighthearted question that will reveal your date's fun side and sense of humor. If you're feeling cheeky, you can follow with "Would you sing it for me right now?" 

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3. What's your love language?

The five love languages are touch, words of affirmation, acts of service, gifts, and quality time. This question helps you determine how your date likes to show and receive love which can help you ascertain compatibility.

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4. What's your best quality?

Asking your date what they think their best quality is reveals what they value in themselves and lets you see a side of them that might only be revealed in time. It also gives them a window to brag a little bit. 

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5. How would your closest friends describe you?

You might know how they'd describe themselves, but asking how their friends would describe them will provide a different perspective entirely. It will also provide you with some insight into their friends and group dynamics. 

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6. What's your biggest flaw?

You might want to share one of your own flaws before asking this question. No one is perfect, but understanding their worst quality early on will help you understand the full picture better and know what to expect. 

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7. If you could commit a crime and never get caught, what would it be?

This is a funny question that reveals their moral side. Don't read too much into it, it's just fun to see where their imagination takes them.

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8. What's your biggest turn-off?

Not only will this reveal what not to do, but it says something about your date's values too. If you have the same turn-offs, that can determine your compatibility.

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9. What does "home" mean to you?

This question is deep. It gives you a really good insight into the person's mind, what gives them happiness, and peace. 

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10. What's your guilty pleasure?

Another fun question that reveals something quirky about your date is "What's your guilty pleasure?" Whether it's afternoon soap operas or a terrible band's music, sharing this little secret is a trust practice. It also allows you to gauge whether you could handle their weird little pleasure on the regular.

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11. What's your dream job?

This question is a chance to share ambitions and goals. It gives them an opportunity to talk about their passion. 

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12. What’s one thing about you that most people misunderstand?

This is a great question for getting down to the finer points of a person's personality. Not only does it reveal a potential insecurity and something a little weird about them, but it reveals how they think other people view them. 

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13. What’s the best lesson a past relationship has taught you?

This question reveals something about how your date is in relationships. It also could reveal if there are any leftover feelings you should be aware of, but tread lightly and don't push it if it seems like they don't want to talk about past relationships. 

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14. If money weren’t an issue, how would you spend your life?

This question reveals their deepest desires. It gives them an opportunity to talk about their passions, and turn-ons, and potentially reveal their adventurous side. You can also gauge from their answer how willing you'd be to join them in doing whatever it is they dream of. 

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15. What's your type?

Ask them if they have a type. If their response is solely on appearances, it can reveal how superficial they are. Otherwise, you can ascertain how well you fit into whatever they're describing.

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16. What are three qualities you look for in a partner?

Asking this question reveals your compatibility. If their answers align with what you're looking for and what you possess, it indicates similar values.

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17. What's your idea of happiness?

This question allows you to see what little (or big) things in life give your date happiness. Does it align with the things that you enjoy?

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18. What was your first impression of me?

This is a spicy one! It gives your date an opportunity to flatter you and might get the romantic juices flowing if they're not already. 

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19. What's the most spontaneous thing you've ever done?

Do you like impulsive or cautious people more? This question can help you determine which side of the spectrum they're on and allows them to share a wild story from their life.

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20. If you could live in any time period, which would you choose?

This is a fun and interesting question that can give you some insight into their interests and tastes. If they say the 1960s, for example, maybe it's because they love 60s music or see themselves as some kind of flower child. 

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