The How Long Gone Guide to Holiday Dos and Don’ts

How Long Gone, hosted by creative consultant and columnist Chris Black and podcast producer and DJ Jason Stewart, is described by its creators (tongue-somewhat-in-cheek) as a “bicoastal elite podcast.” And it very much is—you can find the show on the phones of those in dubious creative employ, from lower Manhattan to Beachwood Canyon.

But that descriptor might belie how funny How Long Gone actually is. Black and Stewart’s commentary on pop culture—from Troye Sivan’s “little ass” to Los Angeles’s natural wine epidemic and fellow podcaster Joe Budden’s feud with Drake—have made me laugh so hard that recently, while listening to them make legendary actor Nathan Lane dissolve into hysterics, I nearly plowed into some customers outside the Silver Lake Erewhon (they were probably fans, too). This is not an uncommon experience; one post from the show’s passionate Reddit is titled “got into a pretty bad car crash yesterday listening to how long gone.” “All I remember from when I woke up was that Chris and Jason were talking about Travis Scott and I couldn’t shut it off by the time the EMTs arrived,” wrote the poster. “Humiliating lol.”

How Long Gone episodes, released three times a week, feature guests who work in media, Hollywood, music, fashion, and food. They also do live shows—two are coming up soon in Boston and New York. Since the hosts are warm, professional conversationalists who are well-versed in the art of food criticism and buying things, W has asked them for a holiday survival guide. For the record, Stewart is a big fan of eggnog.

On traveling with maximum efficiency:

Chris Black: The number-one thing to do during the holidays is to fly on the holiday—fly on Christmas Day, fly on New Year’s Day. It’s the most pro thing you can do, because other people want to spend time with their loved ones—but you can just do that the day before and the day after.

Jason Stewart: Clear [for airport security] is a scam. But also I love it, and use it all the time.

CB: In L.A., they banned plastic water bottles, which is tough for me because I only do single-use plastics. But a pro tip is they now sell the large glass Evian at the store, so you’re able to get fluids for your long haul. Whereas, for the past three or four months since this law went into effect, you could only get the little guy.

JS: I’m sure it’s beautiful, but I’m worried it’s going to shatter in my tote.

CB: No, it’s heavy duty. Also, fly first class if you can. That’s obviously the best advice.

JS: Another traveling tip: only go to cities where they’ve booked you for a live podcast, and then you have to pay for the flight and the hotel, but then they give you all this money at the end.

On getting through awkward conversations:

JS: We don’t really have any interest in politics or religion, the things we’re not supposed to talk about at the Christmas table. But we will if we have to—we’ll gladly ruin any dinner if you want to get into the mess with us.

CB: The key is, if you don’t want to go there, don’t indulge people. You have to know how to get around it, which is easier said than done. But I think most people feel the pressure to just give in and be led, and you have to put your foot down.

JS: Once you hit the age where you realize you can just get drunk, then that does help things—as long as you’re a happy, peaceful drunk. Maybe beta blockers could be good for the holiday season.

CB: I don’t want to suggest drugs, but do drugs.

On dealing with drunk people:

CB: Something that I have perfected in my eight years of sobriety is: I will just leave. When I’m done somewhere, I’m out. If people start getting drunk, I don’t care if it’s 9 o’clock, I don’t care if it’s midnight. If I’m in a position where I don’t want to deal anymore, I feel no regret. I feel no remorse. Everyone should adhere to that rule.

On holiday-specific cocktails:

JS: I won’t do a mulled wine, that’s a little too medieval for me. But I do love making a nice eggnog, 1000 percent. But the nog is tough because they go down so easily. As much as I love consuming dairy, it can start adding up and creating a hostile environment in the tummy when it’s mixed with brandy and other liquors. So keep it at two nogs, max.

CB: I’m proud to say I’ve never tasted eggnog in my entire life. It’s never touched my lips.

JS: Make sure you go to Cookbook or a fancy market to buy your nutmeg—and you want to hand grind that, or hand zest it. Never use the powdered stuff.

CB: Don’t worry. The W readers would never use some low-rent powder. That’s not what we do over here.

JS: Hand-microplaned to order. Tableside nutmeg. Don’t use last year’s nutmeg, it’s expired in your pantry. Go to your larder and replace it with this season’s fresh nutmeg nuts. One nut will last you through winter, but you have to buy probably five or six at a time. That’s where they get you.

CB: Oh, Big Nut coming at us again. Coming for our wallets.

On working out over the holidays:

CB: The holidays for me are about killing time. The e-mails have slowed down, Twitter is not as active. I’m bored out of my fucking mind. How much can I read? You have to spend an hour, hour and a half, two hours in the gym no matter where you are, just to make the time go by.

JS: If you don’t have access to a gym or you’re away from your normal fitness zones and the pickleball courts you’re used to, go on a four-hour walk to kill time. Bye, mama. Get your Apple Watch on and maybe change your wallpaper to Snoopy Christmas and just get those steps in. 20k, 30k.

CB: The walk, that’s a common “I got stoned with my cousin” type vibe. But I think Jason’s looking at it more as a fitness, mind-clearing thing.

JS: I am walking to a Popeye’s, so it’s not not getting stoned with your cousin.

On filling the dead time between Christmas and New Year’s:

CB: This is the worst time of year for me. I find it excruciating how boring it is.

JS: I hope you wanted to trigger him, W, because job well done.

CB: I do have several books to get through, and my hope is that all of these streaming services release something interesting to bide our time. But otherwise, I think you have to set a goal for yourself—maybe pick up a new hobby, learn something new, teach yourself something. I won’t be doing that because I don’t do shit like that. But that feels like good advice.

JS: When I was younger, those days in between Christmas and New Year’s were just for partying. It’s Wednesday, we’re going over to Big Steve’s house and turning the three-foot nutcracker into a bong.

CB: Just fire up YouTube, figure out how to fix something in your house. There are so many options for activities.

JS: Stain the deck. Build the deck.

CB: Staining the deck is a great time killer because you got to let it dry. So it could take all day.

JS: Spring cleaning is out, winter cleaning is in.

JS: For our fashionistas, do a closet clean. Get those old Prada coats out and donate them. If they’re cold, you’re cold, bring them in type shit. Also, clean up the cache on your web browser. Remove old, large files from your phone. Also, physically clean your devices: turn your computer off, get in there, clean the fan. Hit it with a little Q-tip and alcohol and the little duster under the keyboard. A digital detox, if you will. 2024, we’re going to be processing speeds amazingly.

On buying gifts for your significant other:

CB: Go to Chanel. No, but I’m a big gift giver. I love it. The key is to pay attention year-round so that you’re not scrambling. Have a few ideas in your head before the holiday rush comes. If you don’t, then you can go wait in line with 100 other people at Chanel in SoHo to spend $1,200 on a pair of slingbacks like me.

JS: I would say, for your significant other, don’t get them something practical.

CB: Don’t give your wife socks. Well, if there are some cashmere socks, that’d be great, but it would have to be part of a larger gift.

JS: Don’t get them a vacuum cleaner.

CB: The Dyson is nice, but it ain’t that nice.