Dining Out During The Holiday Season
Five Rules for a Making Holiday Meal Memorable
There's something magical about dining out during the holiday season. The delightful decorations, the joyful buzz of conversation, the cozy glow of a favorite restaurant that makes even the simplest meal feel enchanting. This is the time of year when every spot seems to add that extra little sparkle—whether it’s a complimentary splash of something festive from the bar, a beloved family recipe gracing the seasonal menu, or warm smiles from staff who know just how to make you feel at home. It is a chance to slow down, savor the moment, and maybe start a new tradition or two. But let’s be honest: holiday dining isn’t without its quirks. Packed tables, busy servers, and the rush of festive first-time diners can stir up a little chaos. So here are five rules to help you glide through the season, embrace the spirit, and make each meal one for the books.
A Little Housekeeping:
If you or anyone you know is looking to connect with more of your community this holiday season, our friends over at Care of Chan are some of the people behind Project Gather and the Times just wrote an amazing overview about their mission / how to get involved.
I had an absolute blast sitting down with Andy and Dom for “Industry Only at The Cheese Store” and I’m still thinking about those Fried Mortadella Sandwiches…
Rule #1: Be Nice to Your Servers
This rule is at the top for a reason. The holiday season is a marathon for restaurant staff—many are working double shifts, sacrificing days off, and putting in the extra effort to keep everything running smoothly. They’re on their feet, managing packed rooms, juggling special requests, and handling the flood of additional orders that come with this time of year. These folks are the heart of your holiday dining experience, and they deserve a little patience and a lot of appreciation. So give them an extra smile, a bit more on the tip, and some genuine thanks—because when you make their night better, it’ll come back around to make yours even brighter.
Rule #2: Find Time to Dine Alone
The holiday season is a non-stop carousel of gatherings, parties, and family dinners, each one louder than the last. Which is exactly why you owe it to yourself to carve out one meal just for you. Back in my New York salad days, my New Year’s Eve tradition was simple: a squash game, a sweat in the sauna, then steamers and cold beers at Pearl Oyster Bar. There’s something about dining solo that lets you decompress, reflect, and just be in the moment. No schedule matching, no small talk—just you, your food, and a little pocket of peace during the holiday madness. Bring a book, or don’t bring anything at all. Just sit, savor, and let the city’s noise melt into the background. After all, a little solitude is the perfect seasoning for this time of year.
Rule #3: If You Make a Reservation, Keep It
Plans change, I get it—but during the holidays, make it a point to stick to your reservation. Restaurants count on this season’s buzz to carry them through the lean months ahead, so every booked table truly matters. A last-minute cancel or a no-show? It’s not just a small inconvenience; it can throw off the entire night and ripple through the weeks to come. Keeping your reservation is more than just honoring your plans—it’s a way of showing respect for the crew working to make your night memorable. It’s a little promise to the people who’ve prepped and planned for your spot. And if you absolutely can’t make it, give them a heads-up early on—it’s the kind of courtesy that makes a big difference this time of year.
Rule #4: Go to That Spot You've Been Dreaming About All Year.
We’ve all got that one restaurant on our list—the spot we’ve been meaning to hit but just haven’t made it to yet. Maybe it’s been sitting there since last year’s best of list, or maybe you pass it every week thinking, “Next week I’ll grab a bite there…” Well, guess what? Now’s the time. The holidays are the perfect excuse to treat yourself to that special meal, to finally make that reservation, and to create a memory that’ll last well into next year. There are places I only went to once or twice, but it was during the holiday season and those meals have stayed with me to this day. They’re the ones that stick, the dinners that live on in the mind long after the season ends. So go for it. Make this year the one where you finally check that place off the list—and make it count.
Rule #5: Share a Meal with the People You Love.
The holidays are a whirlwind, and finding time with the people who matter most is more precious than ever. Make it a point to sit down together—even if it’s just for a casual meal at your favorite local spot. It doesn’t need to be fancy or over-the-top; just set the plan, put the phones away, and give each other your full attention. There’s something honest, something grounding, about sharing a meal this time of year. It’s a reminder not just of the past year but of the people who’ve been there with you through it all. Make these meals about more than just the food on your plates— celebrate the people who make it all meaningful. These are the moments that last well beyond the holiday lights. So settle in, soak up the good vibes, and make some new memories.
Darin sits down with Xander Soren, the founder and Chief Wine Operator of Xander Soren Wines. They chat about his time at Apple, working on game-changing programs like GarageBand, his deep affinity for Japanese culture and he shares some of his playlists that pair perfectly with his pinot. Then we dip into the archives when singer-songwriter Sarah Jaffe swung by to share stories and songs from the latest EP, SMUT.