Boris Jovanovic

10 Deep Questions To Ask Your Boyfriend To Make Your Connection Stronger

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In a 2015 New York Times "Modern Love" article, Mandy Len Catron wrote about a study orchestrated by psychologist Arthur Aron in which two strangers fell in love in a laboratory by staring into each others' eyes for four minutes and asking each other 36 questions. Catron tried the experiment IRL, documented it, and the piece went viral. Is it really possible to fall in love after 36 questions? I'm not sure. I do know, however, that asking questions is key in any relationship. So what are the right deep questions to ask your boyfriend or girlfriend to make your connection stronger?

While it sounds intimidating, I feel like Aron's experiment could, in fact, be a good place to start when thinking about what to ask your partner to get to know them in that next-level deep way. You could even try the whole stare-into-each-others'-eyes-for-four-minutes thing if you're feeling super brave. (I actually did this with strangers in Brooklyn for an internet video, and it was terrifying.)

The 36 questions range from things you may already know about your partner like, "Would you like to be famous?" to hard hitters like, "If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?" I perused Aron's 36 questions and borrowed 10 that I think could help deepen an already committed, love-filled relationship. Here they are:

1. "If you could change anything about the way you were raised, what would it be?"

True, you've probably already discussed your respective childhoods with each other, but the specificity of this question makes it both difficult to answer and pretty telling (not that I'm a therapist). I am struggling to think about how to answer this question, and I hesitate to put my answer into print because I love my parents and they took great care of me; I'd never want them to feel bad. Sharing something this private with someone inevitably will bring you closer.

2. "What is your most treasured memory?"

Marija Mandic/Stocksy

I like this question because while you may predict that your partner will reply with something like "finding out I got into law school" or "my trip to Patagonia," the chances are the memory will be something more obscure, perhaps from childhood. Learning about a moment in your partner's life that you weren't there for is super intimate. (Oh, and this was designed for strangers to answer, so tell them there's no pressure to make it a memory with you.)

3. "What is your most terrible memory?"

Jovo Jovanovic/Stocksy

OK, sorry to be a buzzkill here. This question is not the most fun to ask/answer, but sharing a difficult memory will undeniably bond you and your person. I lost my mom to cancer this year, and it's been tricky navigating certain first dates when terms like "your parents" or "what does your mom do?" come up, but each time I have briefly shared what's going on — don't worry, I don't go full meltdown on first dates — I've felt a bit liberated. Talking about terrible things is healthy, right?

4. "Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items."

This isn't exactly a question, but it is from the list of 36 questions, so let's say it counts. This is fun because you get to give compliments while simultaneously getting them, and who doesn't love being complimented? It's also a really nice way to clearly outline for your partner what you like about them. You can go real meta and say: "I love your ability to state your feelings clearly."

5. "When did you last cry in front of another person? By yourself?"

Kevin Gilgan

Sh*t just got real. Does crying during Savasana during yoga in a dark room count as in front of other people? If so, yesterday. I think this is an important question to ask yourself, as well as your partner. Again, the vulnerability required to answer this will bring you and your partner closer.

6. "What does friendship mean to you?"

This could seem silly because if you are dating you already know their friends well, but different people will answer this in very different ways. See if you and your bae feel the same about what being "BFFs" means. (Maybe you both feel the same way about captioning every couple's photo you post with them "me and my best friend!"... in that it's tired, so no thank you.)

7. "Complete this sentence: 'I wish I had someone with whom I could share...'"

Robert Zaleski/Stocksy

If your partner easily takes offense, maybe this isn't the question to ask them. They might meet you with "Babe, you can share anything with me though. WTF?" At the same time, if you actually answer this question, you're going to share the thing, so maybe it's a win-win? Another difficult question to answer, but very telling.

8. "Share with your partner an embarrassing moment in your life."

Daring Wanderer/Stocksy

Mayyyybe you told your SO about that time you accidentally peed your pants, when in fact you had accidentally number two-ed them. You and your partner probably know about or have witnessed each other doing some pretty embarrassing things. To deepen your intimacy, share an embarrassing moment you haven't told them about or reveal all the details about that embarrassing story you pared down for them early on in dating so as not to repel them. Either way, this is a fun one.

9. "If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven't you told them yet?"

Ryan Tuttle/Stocksy

If saying "I love you" has been an issue for one of you, or if there is a proposal that just can't seem to come slowly enough, maybe skip this question. However, if you really think about this and answer it truly, you're going to find out a lot about your partner. Maybe it's an old boss, an estranged family member, or even an old flame... um, scratch that last one. Maybe try not to bring up exes you wish you had said "I love you" to.

10. "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? Why?"