Can You Find Love In 36 Questions?

I didn’t do it because I thought it would make us fall in love.

Nor did I do it because I wanted to fall in love with him.

I was just curious — intrigued by what the experience would yield.

We met halfway in Madison on a whim. A spontaneous drive to a new city is much more his style than mine, but I didn’t have anything pressing to do, and as the summer wound down, I wondered when I’d have such an easy opportunity again. We only had a day and a half, but it was enough time for an adventure.

On Saturday night, we were sitting in the hotel room, debating if we wanted to go get dinner or head to the bars, or just hang around the hotel for a few hours and go to sleep early. Somehow, we started talking about the 36 questions that lead to love. And we decided to do the first set of questions before heading out to dinner.

I was curious about the questions. I had heard of them before, but never gone through them with another person. I did not believe that the questions alone had the ability to make two people fall in love. The questions manufacture intimacy — yes, if you’re being honest when you answer the questions you will certianly get to know someone better. But I don’t believe that there is a magic set of questions that can produce (and more importantly, sustain) romantic love. Besides, falling in love isn’t the hard part. But we were learning about each other anyway, so it seemed like a good means to that end, to go through the questions together.


We met on accident or fate or however you’d want to say it. The serendipity of our first encounter actually pleases me. Unlike the questions, our meeting was entirely random. It was not planned or contrived or chosen in any way. Many things had to go right for our paths to cross just once. He was visiting Chicago from Minneapolis for an ultimate tournament. I wasn’t playing due to an injury, but the day before the tournament, I decided to go down to watch a friend play.

She was drafted randomly onto a team that he was also drafted on. We met at the fields. I shared the beer I brought with him. I came across several people I knew, and wandered to other fields to talk with them. I watched most of his games, but wasn’t rooting for him or his team in particular. We occasionally talking over the course of the day. When games ended, he offered to drive me and my friend home. We decided to go back to my apartment and then head to the tournament party together.

In my apartment, he said strange things. He started looking around with a confused look on his face. I asked him what he was thinking.

“It’s just, I didn’t think you would own things like this,” he responded, pointing to a few items scattered around. He picked out paintings and knick-knacks that my roommate, who had just moved out, left behind.

I remember being intrigued by how, after only knowing me for a few hours, he had picked up on my taste and style.

He was straightforward, blunt. He wasn’t shy about asking to see my room and going through my things as if we had known each other for years. He asked questions about my family and my values, my religious views, my conception of love. It was unnerving, but also intriguing.

Along with my friend, we sat in the living room sipping beers and talking for hours. Eventually, my friend left to go home. We sat on the couch, talking for a few more minutes. I knew that he wanted to kiss me, but he was emotionally intuitive enough to take any signal I gave him. I’m not entirely sure why, but I told him that I was tired, and he said he would leave. We didn’t exchange phone numbers, or so much as a last name.

When he left, I felt relieved. I was satisfied in my decision to send him away.

But when I woke up the next morning, I had this “what if” running through my head.

That’s the kind of thought that will drive you crazy. What if I stay in tonight and clean the apartment and make a nice dinner and watch Netflix, like I want to. Or, what if I go to this bar tonight. Or what if I go to this one. What if I move to this city. What if I sit here at this coffee shop or what if I sit a few tables down.

Who will I meet and who will I miss? It’s enough to paralyze you to think about it too long. But when I woke up, I had the what if. Maybe I was thinking about Before Sunrise. I don’t know. But I texted my friend and asked her to get his number for me before he left.

We spent a few weeks texting here and there. I wasn’t sitting around waiting for his texts. But about a month after we met, he said he was stopping in Chicago for a road trip. We made plans to see each other.

I didn’t really know what to expect. We went downtown and walked around the gardens and the parks. We walked by Lake Michigan. As we came to the river path, we came across a bar with lawn games. We played giant checkers and cornhole and had a drink. It was then that I realized how much fun I was having.

We had lunch and went on a boat tour. Headed back to Lincoln Park and went to pickup ultimate with my roommate. Then we made dinner and watched TV at my apartment.

After that day, my interest turned to attraction. We started meeting up at tournaments and spending more time together — as much time as we could living 400 miles apart.


In the hotel room in Madison, we went through the first set of questions and forgot about dinner and kept going. For me, the question where I had to talk about my life for four minutes was a difficult one. I would never do such a thing in a normal conversation.

Other than that question, I found that the most difficult questions to answer were the ones where we had to share specifically what we liked or found attractive about each other. But they are also the ones that I remember the most.

When we finished, we weren’t in love. We knew each other better. We probably learned certain things about our compatibility. We probably both felt the possibility for what could happen between us. But the intimacy of what we shared was just that — intimacy, not love. And while that might be a foundation for love, we weren’t there yet.


The most interesting thing, I think, that he said while we answered the questions was that he doesn’t think he’s ever been in love before. I don’t think that I have either. But there we were, both choosing to answer questions that many believed could create love.

And I suppose that’s what I believe about love. We don’t always choose who we are attracted to. We don’t always choose who we meet. But once these initial things happen, couples must choose love. Maybe as humans we can’t help falling in love. But as time goes by, I think that we choose to stay in love. It is this mixture of intangibles and choice that make love what it is — mysterious yet comforting, wonderful yet terrifying.