36 questions for your high school crush

Resurrecting crushes Pt. 2

This past weekend I was able to revisit the memory of what never happened with my high school crush when I took part in the Best of Valley Voices Story Slam at the Academy of Music in Northampton. I told an edited version of the story that appears on this Missed Connections episode of NEPM’s Valley Voices podcast (first story, give it a listen!). 

I’ve returned to this period in my life through storytelling a few times over the past decade or so. There’s this interesting tension I like to explore between my actual first kiss with this guy I dated who wasn’t attracted to me, and the guy who I wanted to be my first kiss but who I was afraid to risk telling how I felt. 

Usually, when I return to this pivotal period, I become fixated on the what-if’s and the what-could-have-been’s, not looking to assign blame, but more in a counterfactual Sliding Doors type way. 

This time when I returned to the story, though, I became very fascinated with what has become of this person I crushed on. We knew each other before the era of social media, and while I have access to the intimate thoughts of people who I met only briefly between 2008-2016, I am not connected to this guy. Nor do I want to search for him on social media sites for fear of being outed as a suggested friend. Incognito web searches have revealed little, and I don’t think I’d be able to answer my most burning questions anyway with information available on the Internet. Because unlike me, I don’t think he’s mining his life for twice weekly Substack posts.

When I was an improv teacher, I did one exercise where students would pair off and answer a subset of prompts from the 36 Questions That Lead to Love questionnaire. Then, they would spend one minute silently staring at one another. To fall in love, you’re supposed to answer all the questions and lock eyes for four minutes, but by just doing part of the exercise, I felt students were able to access some of the key lessons of improv: the ability to see someone, hear what they say, and to speak honestly.  

The questions I have for my former crush aren’t about what could have been. I’m not so interested in whether or not he liked me, especially after listening to the Heavyweight podcast, Episode #53 Leif, about a woman who contacted her junior high crush to find out why he never asked her out. Rather, I want to understand what’s become of this person who I’ve expended intermittent emotional energy on over the past quarter century.  

Like, on a recent vacation, I was riding a train into New York City and looking into apartments along the side of the elevated track, and I wondered what kind of place he lives in and how he gets to work and what that work might be. I’ve compiled my general questions into a thirty-six item survey that I hope will be broadly applicable.     

36 Questions for your High School Crush

1. How often do you receive Amazon deliveries? 

2. How long does it take you to get to work or wherever you spend your days? 

3. Do you ever take public transportation?

4. Who’s the person you’re closest to? 

5. What’s your go to beverage?

6. What’s your favorite restaurant? Splurge? Everyday? 

7. Do you make your own food or does someone cook for you?

8. Who cleans your home?

9. How many animals’ poop do you pick up?

10. Do you like your job?

11. If you had to choose another career path, what would it be?

12. What’s your favorite piece of furniture? 

13. Who is your best friend and how do you spend time together? 

14. How would you describe your style? 

15. How would you describe your home in a Zillow ad?

16. What music do you have on your Spotify, Apple Music, YouTube premium, etc.? 

17. What makes you laugh? 

18. What’s a time in your life when you were sad? 

19. When’s the last time you cried? 

20. Are you close with your family? 

21. Is there anyone you claim as a dependent on your taxes?

22. Is there anywhere you travel regularly? 

23. What’s the best trip you’ve taken?

24. If you could wake up anywhere in the world tomorrow, where would you want to be? 

25. If you could wake up anywhere in time tomorrow, where would you go?

26. What are you faithful to? 

27. What do you root for? 

28. Do you have financial goals and are you meeting them? 

29. It seems too personal to ask about sex, but this is all a bit personal for someone you haven’t spoken to in decades and who might not remember you. Also, it’s hypothetical. And, yes, you probably want to know. So ask whatever you’re comfortable with in this spot or go full on weird and ask your question in the style we read fortune cookies in the 90s (e.g., what’s your favorite color…in bed?). 

30. Do you consider yourself a good person? 

31. Who did you vote for in the 2016 election? 2020? Who will you vote for in 2024?

32. Is there anyone you say “I love you” to regularly? 

33. What do you like to do when you’re alone? 

34. Do you have any medical concerns?

35. What experiences have changed you? 

36. Where do you see yourself in 5 years? 1 year? Next month? 10 seconds? 

Let me know what I missed. What would you ask your high school crush?

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