Navigating Wine Lists and Confidence: A Conversation with Natalie McLean

I find her refreshing. I find her intriguing. I find her wise: In wine.

Natalie brings to the proverbial table an unabashed view of wine and she will tell you like it is. 

I have to tell you that having Natalie McLean on the show was one of those times where you know you could just keep talking for hours, and still barely scratch the surface. From the moment she cracked her opening line about starting to drink when she met her husband—"and haven't found a reason to stop"—I knew we were in for an episode rich in anecdotes, laughter, and real insight into the world of wine and the people orbiting it. I love a guest who doesn’t take themselves too seriously, especially when that guest has the credentials and accolades to do so if they wanted.

Right off the bat, the story of how Natalie McLean first dipped her toe—well, her glass—into wine was classic. The ex-husband, the MBA couple, and the journey through Spanish classes, golf, and finally onto wine studies left me grinning. You know, everyone’s path to wine is different, but hers, starting with a night course in Toronto after failed golf and Spanish efforts, reminded me that for every over-serious sommelier out there, there’s a person who just wanted to relax after work and stumbled into a passion.

And let me tell you, Natalie McLean didn’t just dip in; she cannonballed. I was genuinely impressed with the way she described her wine education—full sommelier diploma, authoring books like Red, White, and Drunk All Over, and racking up James Beard awards along the way. But what I really admire is her ability to bring it all down to earth. She calls herself the “Chief of Wine Happiness,” which put an instant smile on my face—because at the end of the day, isn’t that what a great bottle is supposed to do?

There’s this refreshing honesty in Natalie McLean about wine’s intimidating side. I shared my own blunders—forgetting wine for family Easter, wandering into the market like any other consumer, grabbing a brand and sometimes striking out. She had her own: sweating bullets in a restaurant interview, staring at a wine list, and famously ordering a Cabernet with Dover sole at a big consulting dinner. Didn’t get the job, but it sparked that classic realization: “I never want to feel that way again.” I could relate—as much as anyone, even after decades in the business, that dusty wine list in a posh restaurant can still get your palms sweaty.

The conversation took a fun turn when she described her divorce tastings—pairing Cabernets with burning love letters. We laughed, but there’s a message in the humor: wine isn’t just labels and numbers; it’s woven into our life’s best and worst moments.

We got onto selecting wine in restaurants, talking to the sommelier, and why confidence is more important than credentials. That tip Natalie McLean gave—to “point at the price” when you don’t want to say it out loud—folks, I’m adopting that one! I appreciated her point: most people just want a glass of pleasure, not an encyclopedia of terroirs. That struck home.

Of course, we got nerdy too—talking about licensing, liquor laws in Canada, and the absurd hoops you still have to jump through to get a good bottle at home if you’re north of the border. Yet, through it all, Natalie McLean kept it relatable and warm, whether it was “free my grapes” in Canada or shelf talkers in American supermarkets.

Put simply, Natalie McLean reminded me and, I hope, everyone listening, that wine is about stories, connection, and yes, a good laugh at yourself every now and then. And that, for me, is what keeps the conversation, and the cellar, alive.