The Look Club
5 min readFeb 12, 2021

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9 Questions That Will Up Your Online Dating Game

How An At-Home Immersive Theatre Experience Gave Me Date Bait

Recently, I went to the theatre. Yeah, I’m in lockdown. And the theatre was a blanket fort I built over my dining room table.

“This is ridiculous,” I thought, as I pulled out my dining room chairs and lay down a yoga mat, “I’m a well-over-drinking-age adult and I’m spending a Saturday afternoon constructing a fort… so I can lie on the ground for three hours in the dark and have a bizarro one-on-one conversation with a stranger.”

It sounded awful; I questioned why I signed on in the first place and kind of wanted to bail. But it ended up being the perfect thing.

I’d been working sixteen to eighteen-hour workdays, every day, Monday through Friday, and I needed to chill. But I didn’t want to just watch TV, and I really didn’t want to work or clean or be on the computer. And I’d already done yoga. I just needed something else. And this… was that.

Also — here’s where we get to the life-lesson-y twist — it wasn’t three hours in the dark. It was an hour and fifteen minutes in the dark (why didn’t they advertise it that way?!) and then (drum roll please) an hour and a half on the phone with a person who “attended the show” last night: Anthony from San Francisco.

Anthony introduced himself with only his first name. I deduced his city later on as he asked me fifty-eight questions, one for every hour “Baby Jessica” McClure was stuck in that well in 1987.

I kept wanting to picture Anthony in New York — he did go to school there, and he seems to run in artsy circles — but six hours drive north of me is where he actually resides. Now, this isn’t a love story. I know, it would’ve been a great one. But Anthony has a girlfriend — she gifted him the immersive theatre experience — and that’s okay; we didn’t have a romantic connection. But we did have a nice time chatting and, what I realized as our conversation was coming to a close is that Anthony, dating prospect though he may not be, now knows me better than any guy I’ve connected with on Hinge over the past six months. That seems insane when you consider that there’s pretty much zero chance he and I will ever connect again. (Although, what the heck, Anthony, if you’re reading this, defy the odds, say hi!).

So, I asked myself: How is a rando immersive experience, whose theme is isolation and loneliness, doing a better job of forming interpersonal connections than, well, most of us dating online? I wondered if it might have something to do with the questions. Let me give you a hint — the ones Anthony asked weren’t:

  • “S’up”
  • “how r u?”
  • “Wanna meet? [during the peak of COVID]”
  • “Any weekend plans?”
  • “How are you holding up during this craziest year in history/dumpster fire that is 2020?”
  • “You gonna take me [to place you traveled to in your picture] next time?”

(For those of you not dating online, yes, these are actual messages guys sent me.)

Instead, the questions Anthony asked were specific, probing. They were intentional and they asked me to reveal something about myself. Some of them did so boldly:

  • “What’s something a stranger wouldn’t know about you?”
  • “What’s something even your friends and family might not know about you?”
  • “Is there anything else I should know about you?”

Others were more guided:

  • “Do you remember where you were when you found out about [historic or cultural moment, e.g., JFK, the OJ Simpson police chase, 9/11, etc.]?”
  • “Do you want to — or have you ever wanted to be — famous?”
  • “Is empathy enough?”

And others were just, well, more refined versions of questions we ask all the time. Instead of, “What’s your favorite TV show?”

  • “What’s the TV show you’ve spent the most hours watching?”

Instead of, “What’s your favorite movie?”

  • “What’s the movie you’ve watched the most times?”

And instead of, “What shows/movies/music styles do you like?”

  • “Is there any show (or cultural work of art, e.g., TV show, movie, musical, music album, play, artwork, book, etc.) that’s changed (or had a noteworthy impact on) your life?”

I usually hate “favorites” questions, and I usually feel like my answers don’t say that much about me. Oddly, I found these questions about cultural content to be easier to answer, less likely to make me feel judged for my answers, and more effective in actually conveying a strong sense of who I am. Interestingly, I felt like Anthony had a really clear picture of who I am. He would be well-equipped to make an informed decision about whether he’d like to chat again (if that were an option). Granted, we were having a phone call, not messaging, as we might have been if we’d met through a dating app. Still, most of these questions are specific enough that they could be concisely answered in a message. And those that feel just a little too big to tackle with one’s thumbs are a great opening for the answerer to say, “Well, that’s a story. Let’s hop on the phone and I’ll tell you.”

There was a moment when I wondered if I should be nervous about Anthony knowing so much about me. It had me reflecting at the end — a reflection I shared with him — that there are certain circumstances in life that grant us permission to trust strangers, permission to engage. One of the stories I shared with him included such circumstances: how a girl I recognized from my subway car let me into her boyfriend’s father’s business to use the phone; how my coworker and I picked up strangers with our rental car and drove them across state lines. Those interactions felt right under the circumstances: 9/11 in Manhattan. But it doesn’t take a tragedy to give us permission to engage and connect. In fact, a dating app does just that. The question is, do we really take the opportunity?

I can’t speak for you, but I know that after spending some time in the dark, now I see things in a whole new light. Thank you, WalkUpArts. And Anthony.

Join The Look Club on Zoom for book-club style conversation about character, connection and the 36 questions for falling in love, Sunday, 2/14 at 12pm PST. Learn more about BABY JESSICA’S WELL-MADE PLAY and how to experience it on www.TheLook.Club

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The Look Club

Eve Weston and Jessica Kantor created The Look Club to discusses immersive media through their site www.thelook.club and reviews of immersive stories.