73 Date Night Questions to Break the Awkward Silence and Start a Convo

by Daisy Mae Sharer
2023-03-20

Have you ever gone on a date and completely froze up because you couldn’t break the ice? You stare at each other, in complete silence, as the room fills will awkwardness. If by some miracle you two get through the date, then the conversations become easier but still… ugh.

Having a few date night questions up your sleeve can be a lifesaver if you’re on a first date. They’re equally great for when you’re with your partner all day – you probably talked enough between seeing them and texting – so having a few questions to ask your partner might be a good idea.

This got Nicole and I thinking of the questions we’ve asked over our dates. Then, doing a big of Googlin’, what else we could find and round-up to act as fun icebreakers and conversation starters.

Here’s what we came up with…

First Date Night Questions to End Those Awkward Silences

These are the questions to try on a first date:

What’s your all-time favorite book/album/movie?
What’s the most fun (or worst) place you’ve been to?
What would be your super power?
What’s your favorite show to binge watch?
Did you hear about Pluto? Messed up, right?
What’s something good going on in your life?
What are some random facts about yourself?
Who’s your best friend? How did you meet?
Do you like staying in or going out more?
Where is your family from?
Ever been to a concert? What’s your favorite one?
What was your favorite class in school?
What’s something you totally obsess over?
What would you do if you won the lottery?
What’s your best talent or trait?
Think you can read my mind? Try it.
Besides what you’re doing now, what kind of career were you thinking?
What’s something cool you like about me? Something you don’t?
What’s a question you’ve been wanting to ask me?
What’s your favorite drink? How do you make it?
What are a few things on your bucket list?
Got a favorite video game or app? Which?

These don’t have to get heavy. Skimp the surface of their interests by asking open-ended questions. Then, latch on to a few good responses and see where the conversation goes. Eventually, you’ll settle into a few topics you both love which will get you two laughing and having a fun time.

Fun Date Night Questions and Icebreakers when You’re Stumped

These are the fun questions you could try during a normal time out:

What’s the worst movie you’ve seen? Best?
What’s the funniest thing you’ve laughed at?
What’s something you’ve always wanted to learn?
What year would you travel back in time to? Why?
Have you ever been on a road trip? Traveled abroad?
Have you ever been caught doing something you shouldn’t have?
What’s the weirdest conspiracy theory you think is true?
What’s your favorite fact?
What’s your motto, creed, or words to live by?
What’s the silliest thing you’ve done money for?
What’s your weakness if you were a super hero?
What would you do if you found a suitcase full of money?
Can you do any impersonations?
What would your 3 wishes be from a genie?
What’s something you can’t explain?
What’s the stupidest joke you always laugh at?
What’s something you wish you knew then that you know today?
What would you do if we swapped bodies?
Think of the silliest safe word, what is it?
What’s one of your “oh crap” moments?
What’s something going on in your life that you’re super excited about?
What’s the secrets we don’t know about you?
What’s the best choices you’ve made in life?
What’s the biggest B.S. you ever heard?

One of the things we like doing during our date night is pulling up some ideas from old writing prompts. Essentially, you’re using the prompt like you would a short story – letting the two of you rift on the idea and just generally have fun exploring the absurdity of it all.

Intimate Questions to Ask Your Partner during a Date

These are the intimidate questions for a date to really get to know them:

How is your relationship with your parents, siblings, and family?
What are you most afraid of moving forward in life?
What are you most excited for in the coming years?
Where would you be if you hadn’t met me?
Are you happy? What’s the good things in your life?
What’s the wildest thing you’ve done in bed?
What’s something you won’t try in bed?
What was your thought of me on our first date?
Do you ever feel jealous of me or who I talk with?
What are you afraid to admit?
What’s something you hate about yourself? Something you love?
What was your biggest fear growing up? What is it now?
Do you want to have kids? How many? When?
How are your finances? Is there anything I need to know?
What would happen if I lost my job? What about yours?
What is your biggest regret? Biggest accomplishment?
Where do you see your career/job going?
Do you think you’ll go back to school? (if they haven’t)
What’s your favorite romantic moment we’ve had together?
What’s your biggest turn on you won’t admit?
What’s something I could do better for you?
Where do you see us in 5 years? 10? 20?
What do you miss now compared to when we first started dating?
What made you choose me versus everyone else?
How do you feel about the current state of politics?
Should we raise our child a specific way? Which way?
What’s something you wish you knew as a kid that you know today?

Keeping a running list of questions somewhere off to the side is always a good idea. Check back through some of your text logs for little tid-bits of conversation you never finished. Or, just ask what’s on their mind and take the time to really listen. Bring those back and keep the communication flowing!

Try These Two Things to Keep the Conversation Going

A lot of the awkwardness of going on a date is overcoming that first bit of conversation. Even then, you kind of feel weird when there’s the silence. There are some giggles, but it goes back to dead quiet if you can’t keep it going.

Two things:

Make a game out of your date night questions
Try a bit of active listening to keep it flowing

Date Night Questions Game

A date night questions game could be like trivia:

Pick a topic you both love
Challenge each other with trivia
Expand on the answers

For example, you could talk about favorite movies. If one of their answers went into how they loved a certain actor or actress, you could quiz them on other movies they’re in. This could delve into side topics like film class or if they’ve created videos before – it opens it up!

Active Listening

The other thing is active listening.

I’ve heard about this and it really works – what you’re doing is basically holding onto the conversation, picking up keywords, and then adding to the conversation by questioning those subtle topics. An example would be if they mention a location when telling a story – and then having them tell you more about that location and why it’s significant.

Active listening is a really good skill to have when building healthy relationships. It should totally become one of your couple’s relationship goals!

What are Your Best Date Night Questions?

We’ve all got ‘em (and sometimes practice ‘em in the mirror)… those date night conversation questions.

What are they?

Feel free to leave a comment with the one’s that get the conversation going!

Have you ever gone on a date and completely froze up because you couldn’t break the ice? You stare at each other, in complete silence, as the room fills will awkwardness. If by some miracle you two get through the date, then the conversations become easier but still… ugh. Having a few date night questions…