I paid $20 to argue with strangers in Old Town—and it was surprisingly heartwarming

Is it your responsibility to talk a friend out of a risky financial decision? Would you leave if you found out your longtime partner was hiding the fact that they’re in significant debt? And do the ultra-rich owe it to their friends to lend them money in times of dire need?

These questions are difficult to discuss even with those closest to us, so naturally, I paid $20 to debate them with people I’ve never met before at The Scout Waterhouse + Kitchen in Old Town.

Arguing With Strangers is a new event from the Chicago-based series Let’s Do Fun Things. Founded in 2024 by Sam Mahafzah, LDFT hosts more than 20 events across the city every month, from board game nights and dance classes to lectures on medical mysteries, pickup beach volleyball and even an adult prom night.

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As with all of their events, AWS is designed to get Chicagoans out of their homes and into meaningful interactions with new people. This was the second AWS event, both of which sold out, and the theme of the night was Money and Relationships. Not a touchy subject at all, right?

The idea is to show up alone, which I did, and be paired with a group of other solo strangers. Often, events like this claim to be inviting for solos but end up being filled with cliquey groups who showed up together. This event, though, was, to my surprise, filled with more than 100 people who also showed up alone.

Before we got into the hot-button issues, we broke the ice with a discussion about whether water is wet (I say yes). Once we’re acquainted, we’re presented with four questions, the last being "Ten years in, you find out your partner did sex work to pay off college debt before you met. They say they didn’t tell you because it wasn't relevant and they were a different person back then. Do you stay with them?"

We were tasked with arguing both sides of each scenario for a few minutes before a representative from each side took the stage to argue their case in front of the crowd. Over the course of the evening, my table dropped the structure, and the debates evolved into open-format conversations.

My group eventually began integrating personal experiences and opinions into the discussion, which opened the door to deeper conversations about relationships, morality and values than I had anticipated that the night would have in store.

I went home with mixed emotions. I was pleased to see people’s willingness to step outside of their comfort zones in a time when isolation and division are the norm. AWS also presented me with the opportunity to look inward and examine my own values. Why do I believe certain things? How did I come to certain conclusions? And have I ever considered opposing ones? 

Signing up to willingly debate delicate subjects with people I'd never met isn’t something I would typically do—and the same can probably be said for many other Chicagoans who aren’t always comfortable stepping outside of their comfort zones. 

The evening ended up being one of the most intellectually stimulating that I’ve had in a while. There are few better things in life than seeing people from all corners of society come together to find common ground, and maybe even friendship. It was a truly heartwarming experience, and in my opinion, $20 was a small price to pay for it.

Let's Do Fun Things hosts events throughout the year. Check their calendar for the latest.