10 Conversation Starters That Take the Blah Out of Small Talk

December 12, 2016

Ah, breaking the ice. It’s among the most challenging interactions one can have. It tests your patience, your intelligence and, most notably, your people skills. Allow us to offer some foolproof advice. Get inspired by our favorite conversation starters that are sure to make small talk a little less awkward. Whether you’re at a wedding, with coworkers at happy hour or turning on the charm at a networking event, keep these instant conversation savers in your back pocket.

1. “I love your shoes! Where on Earth did you get them?”

Flattery is always a safe bet, no matter the occasion. Dole out a compliment and you’ll make a new friend in no time flat. Seriously, though, who doesn’t love a little ego boost every now and again?

2. “Take any vacations lately? Where did you go?”

Forget the weather, travel is the best fall-back topic on the planet. Not only is it far more interesting, you’ll learn a lot about the person in a matter of minutes. Plus, you might even get a cool new idea to add to your bucket list.

3. “How do you know the host?”

If you walk into a party and quickly realize you don’t know anyone, this should be your go-to question. Simple and disarming, it’s a great way to learn more about how you’re tangentially connected. Who knows, you may meet your new best friend.

4. “What did you study in school?”

It’s always a safe bet to ask about someone’s interests. Starting with their academic pursuits will likely get them to open up about their career and what their future hopes and dreams are. This is an especially handy question in a networking setting.

5. “Have you ever met anyone famous?”

There’s a reason celebrity gossip never goes out of style — it’s interesting and ALWAYS gets people chatting. Break out this conversation starter in more casual environments, like a happy hour or cocktail party. The best part of this question is how strange the answers can be. Perhaps they’ve run into Miley Cyrus in a bathroom or crossed paths with Ryan Gosling in a grocery store. These are things you must know.

6. “What’s your favorite color?”

This preschool-sounding question is actually quite fun to ask as an adult. Why? It’s simple, which makes people feel more compelled to elaborate. Ask this question to break the silence in an awkward situation. Not only will you spark a quirky conversation and get a few laughs, you’ll show your fearless side. Not a bad first impression, if you ask us.

7. “When you go to the movies, what’s your snack of choice?”

This is a surprisingly polarizing question. Answers typically fall into three camps: sweet (Raisinets, M&Ms, Snickers), salty (popcorn, nachos) or sour (Sour Patch Kids, duh). Pull this question out if you’re determined to break the “How was your weekend?” mold.

8. “If you could live anywhere in the world, where would it be?”

Who wouldn’t want to daydream about their ideal home? Similar to the vacation question, this inquiry will likely yield fascinating tidbits about the person’s ambitions and wanderlust. Plus, the New York vs. London vs. Paris debate never gets old.

9. “Got any weird talents?”

People aren’t just a resume or an email address or a business card. Answers to this question will prove it. Don’t be surprised if you find out that buttoned-up, well-spoken investment banker is a professional juggler.

10. “Have a side hustle? Tell me about it!”

Chatting about the ins and outs of your 9-5 gets old really fast. Instead, we suggest prying about your conversation partner’s passion project. This gives you an excuse to dig deeper, going beyond the humdrum nonsense of small talk. Mission accomplished.

PHOTO: LESLIE KIRCHHOFF; DRESS LEFT, BOUTIQUE MOSCHINO; DRESS RIGHT, VERA WANG