I had fun recommending these wine pairings with different stages of a relationship for Curve Magazine…

Though Natalie MacLean is about as sensitive to her wines as the average parent is to her children, she still manages to tackle this seemingly snobby, daunting and inaccessible subject with a lighthearted sense of humor that other wine writers sorely lack. Poetic but still down-to-earth, MacLean’s writing is as addictive as her subject itself.

Her journey in pursuit of great wine began with an introductory wine appreciation course, and has since brought her to vineyards around the world, as well as to the World Food Media Awards, where she recently earned the esteemed title World’s Best Drink Writer.

Though she professes to have only minimal skills in the kitchen, MacLean is brilliant when it comes to matching wine with food—even food you might never imagine having with wine. On her website, nataliemaclean.com, she suggests matches for such oddities as nachos (zinfandel), bacon and eggs (semi-dry sauternne), Rice Krispies squares (off-dry Riesling)and Oreos (vintage port).

However, my personal drinking habits usually correspond more to what’s happening in my psyche than on my palate. I had to wonder: What wine goes best with a broken heart? A bad day? A celebration? Luckily, MacLean had the answers to all these pairings as well.

Let’s Drink to this

Award-winning wine writer Natalie MacLean recommends the perfect sip for any occasion.

Trying to seduce a new woman:

Pinot noir: the romantic grape. It’s so difficult to grow and make, but is seductively sublime when it works. I love those from New Zealand, such as Kim Crawford.

Celebrating victory when gay marriage is legal in California:

Definitely a blended wine here, like a shiraz-cabernet from Australia: lots of fleshy fruit from the shiraz, with newfound structure and support from the cab—just like legally sanctioned love.

Nursing a broken heart:

Banyuls and tawny port are the perfect self-indulgent, poor-little-me wines. They drink well with chocolate and most desserts, even a pint of Häagen-Dazs.

Telling a woman it’s over:

Any high-alcohol wine with a bitter finish will do: Italian amarone is probably best. And skip the Riedel glassware in this situation—a tumbler or shot glass is optimal.

Relaxing after a hard day at work:

Pick a wine you can sip slowly, like a German riesling: low in alcohol but high in flavor, so you won’t pass out on the sofa at 7 p.m.

Meeting your girlfriend’s family for the first time:

Try a medium-bodied wine that will appeal to many palates—one without too much oak, tannin or alcohol. I call these switch-hitter wines, as they go both ways, food-wise. They’re good with meat, chicken, pasta, etc. For example, a California merlot from Beringer.

Coming out to your family:

Try a wine from an overlooked or undiscovered region, such as an Argentinean malbec or a South African shiraz. Your family will be pleasantly surprised at how palatable both the wine and the news can be.