cute couple questions
Relationships, Resources

35 Questions That Lead to Important Conversations

While you may have asked each other some of these questions in the past, your answers can always grow and change. It’s important to continue learning about your boo every day–30 days or 30 years into the relationship!

Next time you have a date night, ask a few of the questions below or knock them out in one fell swoop, talking through the night. Whatever floats your boat! 😉


How would/do you see yourself as a mother/father?

How many kids did/do you see yourself having?

What did you learn from your parent’s marriage? 💍

Is there something specific you want to do or avoid doing that they did? 

Would you stand up to your family for me? 💪🏼

Do you want to raise kids religious?


What have you learned from your past relationships?

Do/did you have any deal-breakers? 💔

What’s your ideal date?

Would you ever be willing to go to counseling?


What’s your biggest pet peeve?

What’s your favorite childhood memory?

What are your top 3 bucket list items? ✈

When were you the most scared?

What makes you angrier than it should?

What talent do you wish you had? 🎭

What’s the worst piece of advice you’ve ever received?

Do you affiliate with a political party? 🇺🇸

If so, are there things your party supports that you don’t?

Describe your proudest moment.


What’s your worst spending habit?

Do you save money? 💳

Do you have financial goals?

What’s your biggest spending regret?

What’s your retirement plan? 👴🏼 👵🏽


Describe me in one word.

How has this relationship changed you? 💞

What do I do that makes you feel the most loved?

What was your first impression of me? 😍

What brutally honest truth about yourself can you share with me?

What 3 things can we always agree on? ☑


If you could only eat one thing for the rest of your life, what would it be?

Describe your worst haircut. 😰

What superpower do you wish you had? Why?

If you had to change your first name, what would you choose? Why?

Have any questions to add to our list? Let’s talk it out in the comments!
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1 Comment

  • Reply 5 Tips to Make the Most of Your Long Distance Relationship - Datebox May 17, 2018 at 8:49 am

    […] When you feel like all you ever do is talk, you might start to feel like you’re running out of things to talk about. I suggest conversation starters. They’ve been a huge help in my relationship. They not only aid in having more serious and heartfelt conversations, but they can also help things stay light and not so focused on the negatives of being apart. For conversation starters, check out our last post to start building your list of questions.  […]

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