The 75 Best Questions to Ask Your Partner on Date Night

No matter how long you’ve been with your partner, there’s always something new to learn about them. Everyone from long-married couples to brand-new connections can benefit from good, deep conversation—and one of the best ways to get started is through date night questions.

“Open communication is incredibly helpful for making partners feel connected,” explains Tamara Pincus, an expert in sex therapy. These lines of communication are especially helpful in the area of sexuality, since it can be tough to bring up problems or desires both inside and outside the bedroom, she says.

When you’re on a date, it’s a great time to stimulate conversation through open-ended questions. But which are the best questions for date night? In fun or romantic settings (say, at a restaurant or over a campfire) it’s best to keep the questions agreeable, but not necessarily light, Pincus notes. “If you’re out to dinner and able to focus on each other, that can be a great time to talk,” she says. “If you’re at a movie, not so much.”

You should hold off on serious questions that could potentially start a fight until after date night, Pincus recommends. She doesn’t recommend avoiding them altogether—instead, wait for a time when both of you can fully focus on the conversation.

The ideal date night questions will make you feel closer to your partner, revealing thoughts, wishes, or memories that you might have never discovered otherwise. Answer each one as truthfully as possible—and if you’re the one asking the questions, be mindful of any potentially thorny topics that could put a damper on your date, and keep them in mind for later.

Read on for a list of great date night questions, many of which come directly from Pincus. Now ask away!

What is making you feel alive lately?
Is there a song that makes you think of me?
What’s the worst job you’ve ever had?
If money were no object, what would you buy first?
When you envision our future, what does it look like?
Do you need anything more from me in our sexual relationship?
Do you need anything more from me in our romantic relationship?
What in your life makes you feel most grateful?
What was your first impression of me?
What do you like to do when you’re alone?
If you had to completely change careers, what would your new job be?
What can we do to make a real difference in the world?
What’s your favourite movie, and why?
When was the last time you felt scared?
Which of your parents are you most like?
Is there anything you’ve dreamed of doing for a long time? What’s held you back?
What’s one thing I don’t know about you?
What do you admire most about me?
If you could fly anywhere for free right now, where would you go?
If you could become famous overnight, would you?
Do you believe in fate?
What’s the best gift you’ve ever received?
What’s your favourite activity to do together?
Who was your first celebrity crush?
Do you have a least favourite word?
What’s an album you could listen to every single day?
When do you feel most loved by me?
What are the things in this relationship that are really working for you?
Is there anything in our relationship that isn’t working for you?
What do I do that brings you the most pleasure?
Can you remember a perfect day from your past?
What’s your worst habit?
In what ways are we similar? How are we different?
When was the time you’ve felt the most embarrassed?
Do you salt your food before or after you taste it?
What’s your favourite season, and why?
When did you first know you loved me?
How often do you like to have sex?
Is there anyone you wish you had never met?
What’s the worst advice you’ve ever gotten?
Where would you like to live when we retire?
Other than your parents, who are the two people who have made the most impact on your life?
What’s something you look forward to every day?
If you could live in any era, past or future, when would you choose to live?
What’s something you wish you were better at?
Is there anything that’s interesting to you sexually that we haven’t talked about or tried?
What is your favourite museum, and why?
What did you want to be when you grew up?
What’s your biggest accomplishment?
Who were you in high school?
Do you believe in ghosts?
What’s your biggest unrealistic fear?
Are you a planner or a procrastinator at work?
What’s the best sex we’ve ever had?
What’s the best kiss we’ve ever had?
When was the last time you expressed your creativity?
What do you find sexiest about me?
What are you looking forward to in the coming week? Month? Year?
If you could only eat one food for the rest of your life, what would it be?
Do you have a favourite scent or smell?
What makes a kiss particularly enjoyable?
If you had to choose one sense to lose, which one would it be?
What’s something everyone likes that you don’t?
Out of everyone you know, who has the best relationship? How can we make ours look like theirs?
Have you ever played with a sex toy?
How many times have you been in love?
What’s something small you’ve done for me recently? Did I notice it?
What will the world look like in 10 years?
Would you ever consider an open relationship?
Do you prefer walking or driving?
Is there anything you’ve always wanted to know about me, but haven’t asked?
What could I do to make your life easier?
If you could be one age for the rest of your life, what age would you choose?
What’s the funniest thing that’s ever happened to you?
When do you feel the most comfortable with me?