My grandfather never met a stranger. I used to think it was just a West Texas thing, but no—it was a him thing. Whether it was the cashier at the grocery store or a couple making out in a parking lot, he had a way of wading into their lives, feet first, like he already knew their third cousin and their dog’s name. As a kid, it was mortifying. I wanted to melt into the floor while he cheerfully asked the waitress if she was having a good day or told the guy at the gas station he looked like he knew where the good fishing spots were. The man could disarm a feral cat with his charm. Or annoy the hell out of it. It was a coin toss.
But, I have to give it to him—he taught me the one social skill that continues to serve me better than either of my advanced degrees: the art of conversation.
From Mortification to Mastery
Even though I hate small talk with the fire of a thousand suns, I’ve somehow become that exact person. I’m the one saying to the woman in the Walgreens line, “Do you think anyone actually buys these greeting cards, or are they just here for decoration?” Or pointing at a jar of pickles and asking someone next to me, “Are you a dill or a bread-and-butter person? Choose wisely.”
It’s exhausting, truly. There are days I want to wear a sign that says “I am simply not accepting conversations today.” But then there are other days where the chaos takes the wheel.
Conversations for Chaos
One time, Matthew and I were walking through a store and he casually mentioned that not many people had Amazon Prime. So, naturally, I made it my mission to ask every person we passed if they had Amazon Prime. The reactions ranged from startled confusion to nervous laughter, which is kind of my sweet spot.
I’ve also been known to whisper “Call the cops. He’s bothering me,” while gesturing at Matthew in the cereal aisle. People blink. Pause. Then crack up once they realize it’s a joke. He says he hates it, but I suspect it’s part of my charm offensive that he secretly enjoys. (And let’s be honest, that man is too patient for his own good.)
Why Small Talk Matters (Even When It’s Exhausting)
Small talk has this reputation for being shallow, a filler for silence. But I’ve come to see it as the warm-up act. It’s how we test the waters of connection. A shared eye-roll about the weather, a quip about someone’s choice in produce—these are the toe-dips before we dive into deeper conversations.
And in a world that feels increasingly disconnected, that moment of levity with a stranger might be the only real human interaction they get all day.
Still, it drains the life out of me sometimes. There’s a performance element to it, especially when you’re gay, biracial, and managing three hotels in a state where “hospitality” can mean both sweet tea and side-eyes. But I keep doing it. Because somewhere in that performance, real connection can still bloom. Even if it starts with a joke about Prime memberships or an unsolicited pickle survey.
Conversation Starters That Keep Things Weird
And sometimes, I just like to stir the pot. Here are a few of my favorite go-to conversation starters, each with the potential to go charming or chaotic:
- “Have you ever met anyone who actually likes candy corn?”
- “I have a theory that people who buy pineapple on pizza are also morning people. Thoughts?”
- “Be honest—are you here for the shopping, or just trying to escape your family for 30 minutes like me?”
- “Do you think this shirt makes me look like I believe in astrology?”
- “If the world ended tomorrow, what snack would you hoard?”
- “Do you think Target employees know we treat this place like our second home?”
- “Okay, we’re on a sinking ship. You get one celebrity to save. Who is it?”
Each of these could crash and burn, or launch an oddly profound five-minute exchange with a stranger who needed a moment of levity.
Here’s the thing: small talk doesn’t have to be polite. It can be weird, provocative, sarcastic, or just plain nosy. As long as it’s human. As long as it breaks through the mindless scroll and silent checkout lines and says, “Hey, I’m here. You’re here. Want to be awkward together for a second?”
So here’s to small talk—awkward, often unnecessary, occasionally hilarious small talk. May it never be deep, but always be a doorway.