When my parents betrayed our bohemian roots by moving from the heart of Greenwich Village to the Upper East Side, I encountered many peculiar characters, all in small doses. There was the queen of the co-op board, who never failed to slip me the side-eye and refused to touch the elevator buttons with her bare hands. There was the building’s super, who strutted around in a white ribbed tank top and silver chain, snaking drains and making wisecracks. But the person I remember most vividly, and with the most affection, was the night doorman.
Whether I walked into the lobby at 10 p.m., giddy from a goodnight kiss, or 1 a.m., drunk off of my parent’s (stolen) gin, Lenin would greet me with a warm welcome and polite chit-chat. He had the distinct ability to engage people past the superficial: He remembered birthdays and referred to pets by name. Although the conversations never lasted too long, they always stayed with me, lingering in my mind like a catchy refrain. He was, and still is, the unsung hero of the speedy heart-to-heart.
I’m always reminded of his talent around the holiday season, when the small-talk demands grow taller than the Rockefeller tree. How would Lenin engage with my partner’s middle-aged boss, or my friend’s old roommate from college, or my second cousin’s longterm fiancé? In order to glean his wisdom—and that of similarly professional small-talkers—I decided to catch up with him and ask. Below, learn how Lenin, Kimberely (a yoga studio receptionist), and Cora (a server) keep their chit-chat in tip-top shape. Then walk into all your seasonal gatherings with your head held high and nary a desire to spend too much time petting the host’s dog.
10 Tips for Better Small Talk, Per the Pros
Start the conversation with a compliment.
“If I feel like your hair looks good, I’m going to tell you just that. In my experience, it can open up a conversation—even if it’s a superficial one about products. Do you know how many hairstylist recommendations I have gotten over the past few years? Enough to start my own magazine.” —Kimberely, 27, works at a yoga studio in Tribeca
Be willing to veer into unexpected topics.
“The trick to making small talk is letting yourself be surprised by the conversation. Try not to have a rehearsed conversation outline in your head because it closes you off to making an actually organic connection. I think a lot of people enter these types of interactions with an idea of how it’s going to go, and that ends up limiting the conversation. If you truly just enter with an open mind, people will really surprise you (for better or for worse).” —Cora, 24, works as a server at a restaurant in Hell’s Kitchen
Grow accustomed to the sound of your own voice.
“If engaging in small talk doesn’t come naturally, practice with yourself. Learn to be completely comfortable hearing the sound of your own voice. In my experience, it’s not the choice of words that matters, but how you say them.” —Lenin, 40, works as a doorman on the Upper East Side
Ease other people’s anxiety with a warm, toothy grin.
“When entering an unfamiliar space, some people can be very withdrawn or nervous. A smile and a kind greeting have the power to immediately make someone feel welcomed and comfortable.” —Kimberely
Use each exchange as an opportunity to learn something new.
“I use every conversation I have with clients to enhance their experience and walk away having learned something new. For example, if a couple comes to celebrate their anniversary, I ask questions and about their origin story of how they met and fell in love.” —Cora
Be the Nick Carraway of small talk.
“Stay in-tune with current events, the weather, media, gossip, style, business, unfortunate tragedy, food, etc. Be highly observant of people around you, but casual. Pay attention to how they react, the sound of their voice, how they dress, what they read. Are they observant as well? How do they react toward you? Anything can slowly engage or spark small talk.” —Lenin
Lock eyes and actively listen.
“Own your space. Look people in the eye while they’re talking and listen. No matter how little they have to say, you never know how lending a listening ear can impact someone’s day.” —Kimberely
Remind yourself that this is about them.
“Don’t take anything personally. Small talk is inherently brief, so most of the time a person’s reaction is not about you. I treat everyone I meet like they are my teacher. Because they are.” —Cora
Tailor your topics to the person you’re talking to.
“You cannot talk about romance with someone who just got divorced. Don’t bring up death or loss to someone who just had a baby. And absolutely do not forget to listen! Convince yourself that anyone and everyone can be interesting and that you can be found interesting by anyone. Take pleasure in being a part of someone’s memory with a compilation of moments. Never doubt the possibility of having a great impact or influence on someone with just a few memorable words. If you allow it, it can go as far as the start of a friendship, or job opportunity.” —Lenin
Do yourself a favor and skip the weather.
“That’s just corny and a waste of everyone’s time.” —Kimberely
This story is part three in “How to Do Anything,” Man Repeller’s how-to service franchise that rave reviews are calling “better than Google” (just kidding—but seriously, it’s like a search engine combined with a metaphorical pal who cuts out the ancillary information to tell you exactly what you need to know, and what’s better than that?). Did you know you can also learn how to clean sneakers and finally wash your sweaters? Click away!
Photos by Meghan Marin.