How to Start a Captivating Conversation—Even If You're Shy
Recently, I was at a party and I noticed myself obsessively checking my phone, wondering if the entire evening would be a bore, when I saw a silver fox eyeing me from across the room. When I glided over and said hello, he responded with a four-word question that made me cringe: “What do you do?” Suddenly, I realized why I was feeling bored and down—I had spent the last hour and a half having the same conversation over and over again. The last five people had all asked me what I did for a living and I ended up repeating my spiel (“I’m a writer, personal chef, and event planner!”) over and over again.
Because I believe that meeting new people at a party shouldn’t feel like a job interview, I’ve simply stopped asking people what they do. If this idea seems foreign and scary, keep reading. Here’s how to start up a provocative conversation with an unknown at a party.
This is the easiest and most obvious conversation starter. You’ve ended up at the same place for a reason, so you must have a connection through the host of the event. Base your next question on the response. If it’s a family member or long-time friend of the host, ask them to share a funny memory. If it’s a colleague, ask why they enjoy working with the host. If it’s a new friend, ask how he or she met the host.
Do anything else fun beside this party? Parties usually happen on weekends, and weekends are usually leisure time, so why not ask what they have been up to? The answer possibilities are endless. so take a deep breath and go with it. If they reply, “I hung out with some friends, drank Old Fashioneds, and watched the first three episodes of Friday Night Lights,” smile and say, “Thank you! I haven’t thought about Tim Riggins in way too long.” Or, if you’ve never watched the show, ask them to explain the pilot episode to you.
Examples: Have you seen any of the movies that were nominated for Best Picture at the Oscars? What colors did you see: white and gold, or blue and black? Which teams are your top seeds for March Madness?
There is always a holiday—whether it be a major festivity like New Year’s Eve, or a commercial celebration like St. Patrick’s Day—just around the corner. If you happen to be at a party that is in honor of said holiday, use this as a jumping-off point. Where did you find your red velvet suit? It’s perfect for your Beetlejuice costume! What are you most looking forward to eating tonight? I just can’t wait for the gravy. The turkey is really just a vessel for gravy, don’t you think?
Insert an adjective like gorgeous, freezing, or sunny. It may be cliché, but I love talking about the weather. There are so many ways to go about it! Wasn’t today the most beautiful day? Did you know it was supposed to rain today? Did your power go out during the storm? When I learn that a person has recently moved to California from the East Coast, I can’t help but ask, “How did you survive the winters?!”
Participating in an activity—even if it is as simple as heading to the kitchen and pouring a glass of wine—is a good way to get to know someone. Along the way, ask about his or her preference in spirits. Are you more into wine or beer? Do you ever make cocktails at home?
What’s your power animal? Did you read Fifty Shades of Grey? Have you ever been to Buenos Aries? Yes, these are actual questions that I have used in the past month to start interesting conversations.
Questions that are too open-ended or general, topics that are super controversial, and anything that is too personal.
Lastly, remember that not all silence is awkward—if there is a natural pause in the conversation, don’t freak out. Let the pause happen and move to the next starter. Being a good conversationalist means you’re also a good listener, so pay attention to what the person is saying and look he or she in the eye. Keep things light. It’s a party—you should be having fun!
Find more of Katie Sweeney's expert entertaining and cooking advice at Six Twists.
What conversation starters do you swear by? Tell us in the comments below.