6 Expert-Approved Conversation Starters to Try This Holiday Season

6 Expert-Approved Conversation Starters to Try This Holiday Season

Right now, your calendar is probably brimming with holiday parties and cocktail soirees. Oh what fun! And, oh — what small talk! As you mix and mingle, it can be challenging to keep conversations engaging, even if you consider yourself an extrovert who loves meeting new people.

As master conversationalists know, there’s an art to conversation. Subtly tweaking a question from, “What are you doing for work?” to, “What’s keeping you busy these days?” allows others to talk about what they’re passionate about (which may be something other than their careers).

Also, be careful of some known conversation killers. Bringing up the weather or traffic gets old. And as for political conversations at holiday gatherings? It’s best to avoid them like stale fruitcake. Admittedly, this is tough to do as politics have seeped into most aspects of our lives. But, the majority of people want a reprieve from talking about politics at parties — a poll from Quinnipiac University found six out of 10 Americans want to avoid political discussions this holiday season.

So, what are some great conversation starters? We turned to experts well-versed in communication to share with us some of the questions they ask to evoke meaningful or fun conversations. Then, we flipped the script, and had them answer their own questions.

This holiday season, as you make your rounds on the party circuit, consider this a gift of gab.

“What’s your favorite holiday tradition?”

Conversation Starters: Alex LeventisOftentimes, people have similar holiday traditions, like hiding a pickle ornament in the Christmas tree or opening up a gift on Christmas Eve, which creates an instant connection, says Alex Leventis, who works for a cybersecurity startup in Chicago. He’s also created a forthcoming app called Rumble that pairs users of opposite stances on social and political issues and lets them debate. (That way, you have an outlet other than the dining room table to debate politics!) Asking about traditions will give you a glimpse into others’ family lives, and also spur follow-up questions like where the tradition originated from.

Here’s how Leventis would respond to his own question: “Every year on the day before Christmas Eve, my family goes to Kentucky Fried Chicken,” he says. The tradition started when he was 10 and his mom was preparing to host a Christmas dinner, and, as she was preparing the roast beef, the oven malfunctioned and set dinner on fire. “As a last-ditch effort, my dad ran to the nearest KFC to feed our hungry guests,” Leventis says. “We now go every year.” His family also has a Greek tradition of baking a sweet bread and putting a coin in the bread before it goes in the oven. “On New Year’s Day we enjoy the bread and whoever gets the piece of bread with the coin is considered to have good luck all year.”

“Tell me about a recent trip you’ve taken.”

Conversation Starters: Laura ArieliGreat bartenders know how to keep an entire bar rail of guests engaged. Asking someone about travel — whether it’s a past trip or an upcoming one — is a go-to question for Laura Arieli, a bartender at Roka Akor, a sushi restaurant and Japanese steakhouse. “It’s a great way to find out more about the other person and what interests them,” says Arieli, who works at the Old Orchard location in Skokie.

Here’s how Arieli would respond to her own question: “A couple months ago I took a solo trip to Barcelona and Ibiza. While there, I got to explore the culture and saw a lot of stunning artwork by Gaudi,” she says. “This trip in particular also gave me the chance to have alone time and find my inner self.” She also traveled to Medellin, Colombia, earlier this year and was fascinated by the Rock of Guatape. After climbing 650 stairs, she was rewarded with a breathtaking view. She’s eyeing Thailand or Iceland for future travel.

“What would be your perfect day in Chicago (or whatever city you live in)?”

Conversation Starters: Jeff MikosTalking about travel is always a fun conversation starter, and that can include playing tourist in your own city, says Jeff Mikos, the owner and operator of Free Chicago Walking Tours. He leads free, two-hour walking tours through Chicago’s most iconic neighborhoods and is tasked with keeping the conversation going among groups of travelers who come from all over the world. (This year they introduced a special winter tour schedule with tours of the Chicago Pedway and a new Holiday Tree & Light Tour). For locals, though, he likes to know what Chicago tours, activities, or attractions are on their lists.

Here’s how Mikos would respond to his own question: His favorite guided tours are the architectural boat tours along the Chicago River, and he does one every single year. As for his Chicago bucket list? Here are a few highlights that make his list: dinner at Alinea, a helicopter ride over the city at night, and a ride on the holiday Metra car.

“What do you want to accomplish in 2019?”

Conversation Starters: Kelly RussellAsking about New Year’s resolutions can be a bit personal. (Who wants to divulge their weight-loss goals in between sips of eggnog?!) Instead, take a page from Kelly Russell, a preschool teacher and author of “A Girl’s Guide to Chicago,” and ask your conversation partner a broader question such as what they want to accomplish in 2019 or what’s on their vision board.

Here’s how Russell would respond to her own question: “I created a vision board checklist last year and it helped me not only accomplish my goals, like publishing my first novel, but it also helped me figure out what was most important to me and helped to keep me on track throughout the year,” she says. Among the goals on her 2019 vision board? Working on a second book and marketing her current one, as well as traveling to London and Paris.

“What type of creative work do you do?”

Conversation Starters: Luann UdellThis might center around what someone does for a living, but it opens the door to talking about other passions and interests, says Santa Rosa, California, artist Luann Udell. “Most people will respond, ‘Oh, I’m not creative!’” she says. Her response is to tell them that she has a broad definition of creativity. “I think any activity that is a force for good in the universe is creative,” she says. “’Making’ is creative, but so is writing, singing, dancing, acting, nurturing, healing, growing plants, cooking, restoration, repairing, teaching, and so on.” That way, you’ve giving someone “permission” to not just talk about activities and interests that they love, but you’re also validating them.

How Udell would respond to her own question: As an artist and writer, she explains, “I make small artifacts that look like ancient carvings of animals, and use them in jewelry, small sculptures, and wall art. Because I shape them, one at a time, out of layering the clay I use, they look like real carvings from the Ice Age. They feel wonderful in hand, and no two are alike.”

“What has been your biggest life change this year?”

Conversation Starters: David KlowPeople tend to measure their lives by momentous changes, yet day to day we don’t necessarily track all the major things that happen to us, explains David Klow, a licensed marriage and family therapist in Chicago, owner of Skylight Counseling Center, and the author of the new book, “You Are Not Crazy: Letters From Your Therapist.” “Most people can relate to going through a transition in life, and the various emotions that come up,” Klow says. “Talking about life events can be an easy way to connect during the holidays.”

How Klow would respond to his own question: “I got married this year!” Discussing the wonderful emotions that come with a life transition such as a wedding can be a good starting point for conversation and connecting, he says.

Brittany AnasBrittany Anas is a freelance writer who specializes in health, fitness, and travel writing. She also contributes to Men’s Journal, Women’s Health, Trip Savvy, Simplemost, Orbitz, and Eat This, Not That! She spent a decade working at daily newspapers, including The Denver Post and the Daily Camera in Boulder, Colorado, and she is a former federal background investigator. In her free time, Brittany enjoys hiking with her gremlin-pot belly pig mix that the rescue described as a “Boston Terrier” and coaching youth basketball. She also works with domestic abuse survivors, helping them regain financial stability through career coaching. Follower her on Twitter and Instagram.




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