On Tuesday evening, I bolted out of work at 6:27 pm, knowing I had 33 minutes to make it to the bookstore before it closed. The book they had ordered for me, Brat by Gabriel Smith—not to be confused with BRAT by Charli XCX—had arrived, and I wanted to retrieve it so I could start reading it that night. I made it to Three Lives in the West Village, nearly out of breath, just in time for Troy to welcome me in and for Marlowe at the register to hand me my order. I’ve been coming to this bookstore since 2018 when I was an intern. It’s one of my favorite places in New York, and its friendly staff who were once complete strangers to me are now familiar faces.

Knowing it was my last night in the city for a few days (big family party in Pennsylvania this weekend), I decided to treat myself to a dinner out, eschewing whatever haphazard concoction would’ve resulted from the remainder of groceries in my fridge this week. With my new book in hand, I walked to THISBOWL in NoHo expecting there to be a short line (wishful thinking), but I was met with judgmental glares from a line of 20+ KITH customers, Instagram models, and Nolita Dirtbag followers. Dodging the 40-minute wait for a $20 bowl, I continued walking and decided to scope out the wait time at Thai Diner, a favorite of mine. When the situation was the same, I opted for an Angelina Summer Classic: al fresco dining at Café Select.

“Can I sit there?” I asked the host, pointing to the outdoor table in front of the window all the way to the right. This table is somehow always available when I go there. Without looking at the menu, I ordered the field greens salad with chicken and a glass of sauvignon blanc, which is probably the same thing I ordered the last time I sat at that table last summer and the summer before that. Creature of habit.

As I waited for my wine, I was struck with déjà vu and was reminded of a time I dined there with an ex. I remembered the conversation we had that day and pondered how so many of the feelings I had then about friendships and work and New York haven’t changed—for better or for worse—a reminder of consistency in my life, but also a prompt to think about how much has changed. Someone who was once a stranger to me became such a big part of my world and was now again a stranger. I thought about the lyrics from the Ethel Cain song. “Don’t talk to strangers or you might fall in love.”

I’ve long been fascinated by this idea that every person in my life was once a stranger to me. The people I consider my best friends were at one point people I hadn’t met before. When I was a child, I had not yet heard the names of the people I talk to every day—the people I invite over for dinner and send funny tweets to and cry to and say I Love You to. Inversely, some of the people I used to invite over for dinner and send funny tweets to and cry to and say I Love You to are now strangers.

My glass of sauvignon blanc arrived to the table and I cracked open my new book, just having finished my other book, leaning against the wooden bench, crossing my right leg over the left, my black boots scuffed and dirty and in perpetual need of a trip to the leather spa but I wear them every day so I can’t bring myself to go a day without them. I looked up from my new book and noticed a guy about my age doing the same thing at the table across from me on the sidewalk—sipping a glass of wine and reading what seemed to be a new book for him. We made eye contact and I sheepishly returned my glance to the contents in front of me.

After reading the first several pages of Brat, I couldn’t help but notice that Sidewalk Reader kept looking at me. I held eye contact for a second and then pulled out my phone to text my friends the Current Situation.

Me: like should i talk to him lol

Emily: SLIP HIM YOUR NYMBER
Emily: or
Emily: give your number to your waitress to give to him

Me: i have a male server and idk if we’re vibing or not

Jack: Go sit down at the table with him

Me: i don’t have THOSE KINDS OF BALLS JESUS

Jack: Idk man
Jack: Shoot ur shot summer

I had to ruminate on this for a bit.

I sat there for a while trying to read but kept thinking about the idea of strangers. I went through several scenarios in my head of what would happen if I were to somehow start talking to Sidewalk Reader. I thought about whether I would regret it if I didn’t talk to him at all and never saw him again. I also thought about strangers I talked to in the past who ended up changing my life—like the opera singer I met on the train from Milan to Crema who didn’t speak any English but challenged me to have a full conversation with him in Italian, proving to myself that I actually did speak Italian (at the time—RIP); and the girl I met at my summer job in 2014 in a beach town where I didn’t yet know anyone, who then became a friend for life; and the girls I met at the Perfectly Imperfect party at Baby’s All Right in 2022 after my friends left me, which ultimately opened me up to New York’s downtown scene; and the plus ones of plus ones who I met at my own parties who then became the invitees.

My salad arrived and as I was slicing the grilled chicken, Sidewalk Reader was still looking at me. He ordered another spritz, so I ordered another glass of wine. Two can play at this game. I texted Emily.

Me: i’ve invested another $12 glass of wine in this tension
Emily: ok chief what are we gonna do

I started laughing out loud. In: calling people chief.

Sidewalk Reader noticed me laughing at my phone and smiled. Now tipsy off my 1.02 glasses of wine (lightweight), I smiled back and motioned for him to come sit with me. Me? he mouthed, pointing at himself while rising from his table. “Do you want to join me?” I asked. He moved his spritz and his book to my table and told the server to transfer his bill. He told me his name (we will still refer to him as Sidewalk Reader) and I could hear he had an Italian accent. “Where are you from?” I asked. “Rome,” he said. “I used to speak Italian,” I said half to myself, thinking about the opera singer from the train. I hope he’s well.

We sat there and talked for 3 hours. It felt like a date, but it wasn’t. I don’t think we had a romantic connection, but we certainly had a let’s-yap-on-the-sidewalk-on-an-unassuming-Tuesday-night-for-3-hours connection. He told me about his family and about growing up in Rome and about sailing and about working in finance and hating your job and about how Americans eat dinner way too early and Caffe Reggio sucks. (No it doesn’t.) I told him to quit his finance job and he told me he needs it for his visa unless I want to get married and get him a green card. I told him I’d think about it. He told me he knows how to get a reservation at Roscioli. I told him I’d really think about it. We contemplated another drink but ultimately decided our 3-hour conversation was enough for one night.

It was 11pm and I had to go home to go to bed because I’m American.

It was 11pm and he had to go home to make dinner because he’s Italian.

He wrote his name and number on a Café Select postcard and drew a smiley face because that’s the tattoo he has. I walked home giddy, not because I had a crush (I didn’t), but because I felt my faith in humanity restored. I was reminded that we have things in common with every person we meet. I was reminded that everything happens for a reason, and if the line at THISBOWL was fewer than 40 people, I wouldn’t have had a flourishing conversation with Sidewalk Reader, whom I’ll probably never see again unless he invites me to Roscioli and then we have to get married after.

I’m going to talk to strangers more.* I’m going to start more conversations in real life. I’m going to continue to read my books in public instead of my screen, in hopes that this makes me more approachable. I’m going to continue to dine alone because that’s how my Substack started and it’s been almost a year and it’s changed my life for the better. (!!!!!)

TALK TO STRANGERS! x

*I don’t recommend talking to people on airplanes. Unless you really feel like the conversation is going to be absolutely necessary and life-changing and well received, it’s kind of annoying to do this and Mom I know you’re reading this and we disagree on this but stop talking to people on airplanes.

✯¸.•´*¨`*•✿ ✿•*`¨*`•.¸✯✯¸.•´*¨`*•✿ ✿•*`¨*`•.¸✯✯¸.•´*¨`*•✿ ✿•*`¨*`•.¸✯

Afterward

March 14, 2025: Wow wow wow. Publishing this essay changed my life in so many ways, and I am forever grateful for how much it’s resonated with readers because I truly feel like I’ve made a difference for some people, and that means more than likes and subscribes and all that jazz (even though I’m so grateful for that too!). I received an Instagram DM a few months ago from an anonymous account saying that this essay has helped them overcome social anxiety more than their therapist has, and I think about that all the time. It really says a lot that this story has touched so many—there’s something to be said about thousands of people all wanting the same things: Community. Kindness. Things in common with their peers. Love.

I’m so grateful for all of you. A lot of people ask me if I’ll ever adapt this into a book—I would love to. I want to. Please continue to share, and if you have the means, please consider becoming a paid subscriber to Lunch on Friday (so that one day I can quit my 9-5 job and write novels and sit on sidewalks talking to strangers).

Thank you for reading.

xx Angelina