TL;DR: People in Chicago are easier to talk to than in other cities, and it’s made for good times and real friendships–especially at Lula Café.

The thing about people in Chicago being exceptionally approachable is true, in my experience. It’s been much easier to strike up spontaneous and sincere conversations here than it was in Boston or New York, where I’ve lived before. Just saying hello on the East Coast can feel like heavy lifting. I’ve heard Los Angeles can feel even more rigid.

This difference has been on my mind because I was just at Lula Café in Logan Square and ended up chatting with the guy next to me. It basically turned into us having lunch together. That’s happened to me about 30 or 40 times in the past year at Lula Café.

Sometimes I go there to eat alone with a book. Most of the time, though, I end up chatting with other bar-goers. There’s often no expectation to exchange contact information—it’s a mutually understood catch-and-release friendship for the meal. Other times, we’ve swapped info, stayed in touch, and gone on to make close friends with each other.

Here are a few recent examples:

During Halloween, I sat next to an older woman visiting from out of town who said she “had to try out Lula Café.” She turned out to be a retired linguistics professor preparing to sail around the world with her husband. We wound up sharing a meal together. Before heading out, she invited me to visit her sailboat in the Upper Peninsula. I’m planning to go this summer. Pretty cool?

In December, Ruth, the bartender, asked me what I was doing for the holiday break, and I said (not sure if you’ve heard this yet), “I’m going to Japan.” Weirdly the guy to my left and the two guys to my right had just come back from Tokyo. So it was like a Connect Four of guys at the bar who randomly really like Japan, and we hung out for a while talking about our experiences there.

A few nights ago, I struck up a conversation with a woman and her daughter at the bar. The woman turned out to have spent 40 years working on chip fabrication at Intel, splitting her time between the Bay and China. We talked about her career, geopolitics, electrical engineering, and her misgivings about the culture of the Bay Area today. Wow?

These kinds of spontaneous interactions would have been rare, and difficult, for me to have in Boston or New York, but they happen often in Chicago. At this point, I think of going to Lula as my best recourse when I don’t have weekend plans.

The “Saying Hi” Part

The initial turning over of the rock and "saying hi" part used to feel unnatural, but now it’s closer to second nature. It turns out that making conversation doesn’t require as much coincidence as I used to think—like, a stranger doesn’t need to be wearing a NYU hat for me to say hi.

That said, I wouldn’t call the ways I’ve made it easier “strategies” in the sense of Pickup Artistry for Making Friends (which would be cringe). But, looking back, I’ve noticed some patterns that work for me, and I’m thinking about them, so I figured I’d write them out.

1. Ask About Their Book

If someone’s reading a book, I’ll ask, “What are you reading?” At Lula, it’s not unusual to see a few people at the bar reading. I’d say four out of five times, we wind up talking for the rest of the meal. Asking about a book is also a nice shortcut to conversation of some substance (e.g. about the Roman Empire, or Robert Caro), instead of lingering on small talk. I like that about it.

2. Ask About Other Things They’ve Brought

A camera is a good example. If I see someone with a camera, I’ll ask them what they’re shooting lately. If people ask about mine, I say, "Mostly stuff for my OnlyFans.” If they laugh, it's a good sign.

3. Offer Up Something About Myself

I’ve gotten better at just being more forthcoming about some more interesting parts of myself, actually. “I just moved here from New York,” or, “I work in toy R&D.” My job happens to be unusual, and that’s handy for starting a conversation. The details give the other person something to latch onto and connect to their experience—Italy, chocolate, toys, research—and build up the conversation.

4. Share a Compliment

“I like your jacket,” or, “Cool backpack.” I’ve enjoyed receiving random compliments enough to start giving them out myself more often. It’s been a nice way to start conversations. I probably do this more with guys than women, if that’s worth noting.

5. Stock Questions

“Do you come here often?” or, “Do you live in the neighborhood?” These aren’t groundbreaking, but they’re helpful for sure. If the person happens to go to Lula a lot, there’s a good chance they like some of the same things that I do about it—hospitality, authenticity, or craft—and that can be a natural entry point.

6. Say What I'm Thinking

This one’s riskier but more exciting. Sometimes I’ll just say whatever I’m thinking at that moment, in the form of a question. Recent examples:

• “So, do you use ChatGPT for anything?”
• “Do you think the invention of the internet has been a net positive or net negative?”
• “Do you think it’s okay for guys to get manicures?”
• “Have you ever done a cold plunge?”

I don’t have some big thesis here—just that Chicago is an unusually good place to meet people, and that’s been a nice surprise. Lula Café is my favorite place in the city to have a meal. No disrespect to Café Mogador, and New York in general, but Lula Café is one of the best restaurants in the world, I believe. Maybe I’ll say more about Lula Café itself some other time. The turkey sandwich is 🔥.

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