How to Keep a Conversation Going

(and Survive a Boring One)

I’ve been a stylist for over 20 years, which means I’ve heard it all.  The good, the bad, and the “why did I start talking about this” convos. Some people can talk to a brick wall and make it interesting. Others? Let’s just say I’d rather watch color process.

Here’s my take: how to actually keep a conversation flowing, and how to save yourself when it’s dryer than dust boring.

Tip 1: Ask Open-Ended Questions

“Yes” or “no” questions are conversation killers. Instead of “Did you like it?” try “What was your favorite part?” People open up when you give them room to talk.

Fact: studies show people enjoy talking about themselves so much that it lights up the same pleasure centers in the brain as food or money. So yes, it’s literally science that people love to share. Give them an opening, and they’ll usually take it. Works on kids, adults, clients, strangers, and basically everyone. I PROMISE!

Tip 2: Find the Chisme (a.k.a. Common Ground)

Everyone has something they light up about…kids, pets, shows, work drama, or even their Costco haul. Listen for that spark and follow it. If their tone gets animated, you’ve found the good stuff. And don’t overthink it. You can always find something in common.

Example: flat-earther or round-earther? At least you both agree it’s called Earth. See? It’s that easy.

Tip 3: Share Something Small

Good conversation is a two-way street. You don’t have to give a monologue, but drop in a story, a funny thought, or even a random fact. Vulnerability or humor gives the other person permission to meet you there.

Pro tip: weird facts are excellent icebreakers. Like, did you know pigs can sniff out truffles better than dogs? You’re welcome… now you’ve got a conversation starter in your back pocket!

Tip 4: Play a Game

If it’s boring, flip it into a challenge. Look around for context clues like the music, their nails, their coffee order, anything. See how many different topics you can introduce until you land on one that sticks.

I’ve gotten up to eight in one sitting. Usually by topic three or four, we finally stumble into the good stuff. Think of it as conversational speed dating…eventually, something will stick.

Tip 5: When It’s Dead… Entertain Yourself

Not every conversation will be electric, and that’s fine. Sometimes the polite nod-and-smile strategy is the best option. Sip your drink, think about dinner, plan your Target run…throw in a few “wow”s or “that’s crazy”s and you’re solid. You’re not a bad person for not vibing with everyone.

Pro tip: if you’re super duper desperate, politics is the ultimate kill switch. It will either shut things down fast or give you instant common ground. BE WARNED: use with caution, this is the nuclear option.

Final Word

Conversations don’t have to be perfect. Some flow and some flop and that’s A-OK. The trick is knowing when to lean in, when to switch gears, when to politely dissociate and channel your inner politician [you know, nod, smile, and look like you care] and when to actually care.

Good luck, and have fun out there, you lil rascals.