Building Intimacy with a Stranger

36 Questions to Deepen Relationships (Part I)

Two men smiling and holding a cup together
Photo courtesy of Dmyrto Z on DepositPhotos
Click here for Part II and Part III

You feel so alive when you share personal stories with someone. It makes you feel connected. Even loved and cared for.

And the more you share and confide, the closer you feel to them.

A research study suggests that when you get to know someone on a more intimate level, by learning more about their lives, you may grow closer to them.

In the study, strangers asked each other a list of 36 questions, beginning with surface topics to increasingly deep ones.

Mary Ann Miranda explores this idea in greater detail, in the context of her own life.

She answers the first 12 questions in her post, “I Think I Love You Part I.” The rest of the questions and her answers are in part II and part III.

Just for fun, I wanted to respond to these questions too, but writing them in the comments wouldn’t be feasible since there are 12 questions and I’m not known to be concise. So I promised to write a separate post linking back to her article.

Self-disclosures in friendships

In my own relationships, intimate self-disclosures do make us feel closer. However, in this study, they ask both partners to answer these questions, presumably with a similar level of detail.

With some of my friends, I consistently share more about my life than they do about theirs.

That’s okay. I know I tend to overshare while many others prefer to talk less. Even after I invited them to share more with me, since I feel guilty about taking up so much space, they still preferred to listen rather than to talk.

It feels unfair sometimes when my friend knows much more about my life than I do about theirs, but I respect their privacy and freedom in choosing how much they want to disclose.

Another friend admitted to me that because I confide so much, he felt obligated to reciprocate in the depth of his disclosures. Not that our mutual deep sharing was a bad thing, however, since we developed a lot of trust and closeness in our relationship. We’re like brothers.

In fact, one reason why I love Medium is that it’s normative and desirable to write about your personal life. So I don’t have to hold back.

I won’t hold back either when I answer these intriguing questions from the research study.  Here we go!


1. Given the choice of anyone in the world, whom would you want as a dinner guest?

Probably one of my best friends. Let’s call her Helena. She is one of the most interesting conversation partners I have ever known, and we have plenty of things in common, too.

Helena and I are both avid writers and poets, for example. And we both care a great deal about social justice. It’s always fun to chat with her and we have dined together many times!

A classy restaurant, with two wine glasses and elegant plates on each table.
Invite your favorite dinner guest. Image by Emprise on DepositPhotos

2. Would you like to be famous? In what way?

Not really. I wrote about how I didn’t want to be famous in another post, “The Perils of Pursuing Fame.”

But I wrote that post four years ago, so my views are more nuanced now.

I’m not too interested in fame, mostly because I don’t want to become arrogant and ruin my relationships with other people. Yet, over the years, I’ve met internet celebrities who are humble, generous folks who still admire and appreciate everyone around them. So I’m not as anti-fame as I used to be.

Rather, I’ve become more fame-indifferent. It would be cool to have a fabulous personality, amazing skills, but not be famous, so I could be a great unknown.

Many people see being “unknown” and “obscure” as something bad. I actually see it as something good. I’m an extrovert and a social butterfly, but I wouldn’t want to be overwhelmed by too much attention from too many people, even if I get no hate mail.

Beautiful blue butterflies in a sparkling blue magical place
I’m a social butterfly, but even I don’t want a massive amount of attention. Photo by rfphoto on DepositPhotos

Plus, and I hope this doesn’t sound awful, I don’t need to seek more attention or to feel more special. All my life, even before I realized I was gay, transgender, autistic, as well as some other minority identities, people saw me as special or unique, though not always in a good way.

Moreover, it’s easy to find attention. As I mentioned, I’m quite extroverted, so I can always find company by chatting with people, even if they are strangers, on some online forum or another, if my friends aren’t free.

There are different levels of fame, too. You could be famous in a specific social circle, such as your friend group, your extended family, your class, your school year, etc.

In these smaller social groups, I feel comfortable being “famous.” The attention is at a manageable amount; and because it’s easy to “achieve fame” here, I don’t have to feel guilty, let alone arrogant.

All you need to do to attain this micro-fame is to talk a lot. Don’t say just anything, but say constructive, interesting things, as often as you can without being obnoxious.

That way, you get noticed and you gradually build a reputation for whatever unique qualities you have.

This is why I easily become “famous” in my classes, extended family, friend groups, and even some online groups. I’m very outspoken and I talk so much that people can’t help but remember me.

But I don’t do this on purpose. I just enjoy chatting and getting to know people.

A close friend, I’ll call her Lana, said that when she first saw me join the WhatsApp Pokemon Go group she was in, she was excited because she thought I was “Facebook famous” — I was “famous” in our Pokemon Go Toronto FB group.

Wow…I know that Lana admires popular people, but I told her honestly that I was simply very talkative. I wasn’t the most skilled, knowledgeable, or even enthusiastic about the game. I was quite middling.

The only thing I was good at was expressing myself in words since I had a lot of practice.

In these little circles of fame, I’m happy to use my “influence” for good. I could help admins resolve conflicts and call out bullies.

In addition, I could do positive things such as sharing good news, demonstrating support for someone, and the like.

To clarify, I don’t actually have that much power, but with my reputation, people tend to trust me and take me seriously. So I can be helpful when it comes to peacekeeping, speaking up for someone, or just being a reliable messenger.

A cute blue and white bird carries a letter in its beak as it flies across a blue background
I could be a reliable messenger. Image courtesy of Kostins on DepositPhotos

3. Before making a phone call, do you ever rehearse what you’re going to say? Why?

Ha, I hate making phone calls! If I wanted to have an important conversation with someone, I wouldn’t use the phone. I would either talk in person or text. So no, I don’t really need to rehearse it.

If I call customer services, I may jot down a few things I need to ask. But aside from that, I’m quite spontaneous.

4. What would constitute a perfect day for you?

It would be great if I had time to read, write, exercise, and meet up with friends in person. I know it’s hard to do all of these things in one day, but it would certainly be pleasant.

5. When did you last sing to yourself? To someone else?

I sing all the time. No, I’m not a professional, and I’m still figuring out my new voice after taking testosterone (I’m transgender). But I do enjoy singing. In fact, as soon as I saw this question, Moana’s “How Far I’ll Go” started playing in my head.

While I wouldn’t call myself a musical person, my mind does spontaneously play songs. Often, the song I sing to myself reflects my current mood, even if I’m not aware of how I’m feeling. So guess what mood I was in when I sang “How Far I’ll Go”!

As for singing to someone else, it must have been a while ago, since I don’t meet up with friends much during the pandemic, and when we do meet up, we rarely sing to each other.

The last time I recall singing anything to an audience was in 2020. I sang “Something There” from Beauty and the Beast to my friends. One friend gave me a look of surprise, as though she expected a much worse performance from me. Another friend said that he liked the French version better, and sang it to me.

Two actors playing Beauty and the Beast, are dancing outside in some garden at night
An artistic rendition of Beauty and the Beast. Photo by KrisCole on DepositPhotos

When I was younger, I felt bad that, barring a few exceptions, people didn’t consider me a good singer and some might even roll their eyes at my singing.

99% of the singing I did in front of others was before I went on testosterone, though, and my voice was higher and more awkward back then.

I’m not saying that people will like my singing voice better now, but my new voice does sound smoother, richer, and more natural than my former one.

6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you choose?

Definitely the body of a 30-year-old! That way, I get the health, vitality, and frankly looks, of my 30-year-old body, but I would also have the wisdom and understanding of a much older mind.

I’d probably grow more intelligent and open-minded over the years as well. When I was a kid and teenager, I was quite foolish and close-minded, but I grew smarter and more openhearted as I went through my adult years.

I’m 31 now, so it’s funny to hear this question about keeping either a 30-year-old mind or body!

7. Do you have a secret hunch about how you will die?

No…hopefully, I won’t be murdered or die in an accident, but who can tell the future? I don’t typically make enemies, but you never know what terrible things people may do.

8. Name three things you and your partner appear to have in common.

I don’t have a partner, so I’ll talk about my crush instead. We are both on the short side (I prefer shorter guys anyway), we’re both good at using words to encourage and motivate people, and we enjoy taking Pokemon Go photos.

A cute ice fox creature gets into a battle stance in the forest
This is Glaceon, an ice-type Pokemon from Pokemon Go. Photo by Sieran Lane

We met in the Pokemon Go battle tournaments, but we are taking an extended break from battling. We hardly even play the game now due to burnout.

9. For what in your life do you feel most grateful?

There’s a lot to be thankful for! But right now, I feel most blessed by my acuity with language. It gives me much pleasure to express my thoughts and feelings in words. It’s fun to tinker with my language to create pleasing, musical effects too, especially in poetry.

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

For one, I wish my parents had raised me to be more self-compassionate than self-critical. And I wish they had encouraged me to take more risks, as they are both highly cautious people.

The more I go through life, the more I realize what I’ve missed because of my harsh self-criticism and my reluctance to take risks.

So I’ve been working hard to develop self-compassion and courage to do things that are unfamiliar to me. You can read more about my thoughts and experiences with self-compassion here.

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

Whoa, I’d have to come out to him as gay and trans first, which is nerve-wracking. I have a hunch that he’s queer too, though I’m not sure. I have no idea whether he’s cis or trans, since many transmasc folks, including myself, are hard to distinguish from cis guys in physical appearance.

Aside from that, I could tell him a bit about my childhood and teen years, since I already told him a lot about my adulthood.

I could tell him that I used to be a loner who was a bully-magnet. My only friends were unreliable and they often became frenemies. But after I got into university, I grew more adept at making friends and had higher-quality friendships as well.

A group of teenagers relax with a cute golden retriever doggo on a sunlit green field
I got much better at making friends and building higher-quality friendships. Photo by Artur Verkhovetskiy on DepositPhotos

Moreover, I could tell him that I used to be obsessed with academics because my self-esteem only came from my grades.

Ever since junior high, when we finally got to choose the subjects we wanted to study, I worked hard to rise up to and stay at the top of the class (or among the top).

At one point, I furiously practiced my French and Mandarin every day, so my French and Mandarin suddenly improved — I transformed from a mediocre student into a distinguished one.

But nowadays, I thankfully derive my self-worth from other areas as well, such as my writing and my social skills. Yes, I know these are based on ability and achievements rather than on personality. But believe me, I’m already doing a lot of therapeutic work to increase my self-esteem through self-compassion.

So far, I’m happy to say that I’ve increased my self-esteem from very low to medium! No, that wasn’t a pun on the Medium platform.

I’d love to learn about my crush’s childhood and teenage years too, and more about his adulthood.

12. If you could wake up tomorrow having gained one quality or ability, what would it be?

It would be cool if I had the power to freeze time so that I could finish all of the things I want to do! This would mean that I would have no more excuses to put off things that scare me, however.


Thank you once again, Mary Ann Miranda, for sharing these questions and your responses. Hope you had fun reading mine, even though some of my answers were substantially longer than the others.

Over to my other readers: How would you answer some (or all) of these questions?

My Part II is here!


Originally published on Medium on March 1, 2022