36 Date Night Questions That Lead to Love (And Lava Cake)

Inside: Trying out the NY Times Modern Love 36 Questions on date night.

How many questions does it take to fall in love?

How many questions does it take to STAY in love?

In 2015, the New York Times Modern Love column ran a story called The 36 Questions That Lead to Love which was later turned into a podcast episode. Basically the idea is that if you and a stranger sit down with these 36 questions, you can get to know one another in such a deep way that those feelings can turn into love.

Already being in a very secure love situation, I wasn’t able to test this out with a stranger. But it did make me wonder, if all it takes is 36 questions to lead to love, then how many questions does it take to stay in love?

I’ve Got 36 Questions and When Are We Eating Is One

My husband and I decided to bring put our spin on the 36 questions and make them date night questions. Not at all for lack of being in love, but for intellectual curiosity and to ensure we did not spend dinner talking about finding the best price on diapers. After 10 years we tend to think we know each other pretty well, but maybe there was some uncharted territory that would make us swoon all over again.

We got all gussied up; Glen even considered ironing his shirt (but didn’t, please, it’s not like we were going to have tea with the Queen). Then we stuffed ourselves full of trail mix, because we don’t know how to eat dinner post 5:30 pm anymore and were ravenous, and made our way to the restaurant. Here’s how we did with the questions:

Question 1:

If you could have dinner with anyone who would it be? Dead or alive.

Glen: Dead.

Becca: What? No. You can’t just pick “Dead.” Like a person…

Question 2:

Gah! Is my dress on backward?

Glen: Ha! Yes, definitely is.


15 minutes prior to this conversation I walked down the streets of Boston practicing my runway walk because I felt so pulled together and fancy. Not exaggerating. Wish I was exaggerating.

Question 11:

Take four minutes and tell your partner your life story in as much detail as possible.

Becca: We good on this one?

Glen: Yeah. Next.

Becca: We’re getting that lava cake for dessert right?

Glen: Of course.

Question 16:  

What do you value most in a friendship?

Glen: Feeling comfortable because so much else can build on that if you are comfortable together. Laughter, support, being completely yourself.

Becca: That’s such a good answer!! Can I just steal your answer? I can’t beat that…

Midway through I turned this into a competition somehow. I could be wrong but I don’t think that was the writer’s original intent.

Question 21: 

Should I care more that the little flame under this fancy bowl of butter is going out every 45 seconds?

Becca: The waiter seems to care a lot and I’ve noticed zero times.

Glen: How bad could slightly less warm butter be?

Question 29:

Share with your partner an embarrassing moment in your life.

Becca: Oh, I know you already know THIS story.

All of the Death Questions:

Glen and Becca: Um, these are super sad… I don’t want to do these ones. Where’s that lava cake?

Love is a Battlefield

In all seriousness though there were some really interesting questions on the list which brought up topics we had somehow skipped over in a decade of courtship. And spoiler alert, we are still in love so it totally worked.

Also in all seriousness, has anyone else ever been to a restaurant that asks if you would prefer a black napkin instead of the white napkin that was provided to you? We both said no and it’s one of the biggest regrets of my life.

Was it a trick question? Was there a prize in the other napkin? Was this part of a larger social experiment and there was someone sitting behind a two way mirror? I’ll never know and that’s devastating.

In closing, grab your significant other or a stranger and try out the questions to see if you can beat our high score.

(Wait, that’s still not the point is it? Whatever. Have fun!)

Read More Marriage Posts:

The Tale of Elliptical Hill

We Have Mice and So Do You

How Do I Do It All? Simple. I Don’t.

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  1. The mister and I have been meaning to go on a date since Little One was born (we’ve only been planning it for nine months or so). I hope our night on the town is as interesting as yours!

    1. It’s so hard to leave the little one(s) at home for the first time, but also very nice to eat dinner sitting down with cloth napkins. So get on out there – and only text the babysitter 13 times, I found that 14 times was overkill. 🙂

  2. After 33 years of marriage, I avoid going out to dinner with just my husband. We have literally nothing to talk about. And we seem to disagree on EVERY topic under the sun. My daughter once pointed out that we often agree on something but NEVER at the same time!!! I am envious of those couples that always find stuff to talk about.

  3. Oh that is so funny! I’ve worn a dress backwards once too. Thankful I’m not the only one.

    I live wiestions like these. They really do help us dig deeper and know each other better.

    Where did they offer s choice of napkins? It totally had to be a social experiment. That’s so crazy!

    1. Right?? It was Flemmings in Boston. I’ve heard since writing this post that the napkin choice is to help avoid lint if you’re wearing blank pants. Oh the fanciness!!

  4. I was cracking up!!! This is telling… ya’ll love each other and can be comfortable with being uncomfortable! I think this is probably how a night out with my husband would go! Always have a light heart! Be willing to laugh! Don’t be so serious>>> lessons I’m learning! Thank you for sharing and adding a bit of comedy to my day!

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