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Whenever you go out on a first date with someone the butterflies are going to stir up in your stomach and you are going to worry about all kinds of things. Sometimes finding something smart or timely to say can be hard, even for the most experienced daters of us.


David and I went out for our weekly date night a few nights ago at one of our favorite vegan bars in Portland. Whenever we go out for date night, we make an intentional choice to put our phones in the middle of the table and try to engage each other in thought provoking, honest, deep… and often hilarious conversation. If you flash back 3 years and found us out on a date night, you would probably see a lot of arguing, making small talk, or us being glued to our phones.

50 first date conversation starters

Not exactly romantic… Eventually, we realized that we needed to invoke a better, deeper form of conversation if we wanted to grow closer. Because of how much this practice has improved our marriage, we decided to compile a list of our favorite questions from the last year for you to ask your partner during date night.

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Gallery Info Stories Resources Contact. If you could relive a year in your life, what age would you choose? What is your favorite memory of us dating?

Perfect first date questions - this is the only list you need

If you could write a note to your younger self, what would you say in ONLY 3 words? What's another career that you think you'd love?

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What was your favorite date you've ever had with me? What do you attribute the biggest successes in your life to?

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How about your largest failures? In what ways are we the same? In what ways are we different? If you could only eat one meal for the rest of your life, what would it be? If someone you loved was killed in front of you, but someone created a copy of them that was perfect right down to the atomic level, would they be the same person and would you love them just as much?

In what ways have I changed since we first met? Is there anything I can do to show you love better? Who is one person in your life that you have a lot of respect for? If you had one mantra to live by, what would it be? What is your favorite thing that I do in bed?

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If you could wake up tomorrow having gained one quality or ability, what would it be? Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be?

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What is your idea of a romantic night with me? Am I a safe person for you to talk to? If not, how can I improve? If I were to die suddenly today, what is one thing you would want me to know?

50 questions you should ask your partner during date night 😉

When did you first know you loved me? What is your biggest fear?

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What would constitute a perfect day for you? If you could change one thing about your looks, what would it be? What's a new hobby you'd like to try?

50 best speed dating questions to start a conversation

What physical feature do you like about me the most? What is one of your favorite memories from childhood? If you could live anywhere in the world for just one year, where would you live? If you could have one super power, what would it be? What makes you feel overwhelmed at work? What would you like more of in our relationship? Do you think you would make a good food critic?

Given the choice of anyone in the world, who would you want to have as a dinner guest? What turns you on most? Is intelligence or wisdom more useful?

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If you could meet one famous person, who would it be? Where does your self-worth come from?

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Which of your parents are you most like? How do you want to be remembered after you die?

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What do you believe you are capable of achieving? When was a time that you felt really close to me? The Final Question: Nuclear war has ravaged our city. Where are we going?

First date questions

Like these questions and want more? Shop our Connection Cards.

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Here is our list of first date questions.


Jasper is our expert conversationalist and wordsmith.


Think of it this way — casual dating is more prolonged, relaxed and easy going.


You need ice breakers, light-hearted queries, questions that provoke banter, laughter, and thought, as well as questions that dig a bit deeper and go beyond the superficial.