Are You Not Entertained?

Chelsea Fagan’s is playing connect the dots – and the dots are Williams Sonoma outlets. Best known for The Financial Diet, the massively popular YouTube channel on which she dispenses blunt advice (while mocking trickledowners), Fagan’s latest book is Having People Over: A Modern Guide to Planning, Throwing, and Attending Every Type of Party, which reads more manifesto than manual. Fagan thinks Millennials and members of Gen Z are fucking up by not having each other over more often – and she’s not afraid to say exactly that while standing between towers of unobjectionable bistroware.

Upper Middle spoke to Fagan about her very specific form of ceremonious rabblerousing.

Most entertaining books assume the reader entertains. Your book doesn’t. You make the case for entertaining. We’ve all got a lot going on. Why are dinner parties imperative?
Look at Boomers. Economically and politically, there's a lot to criticize. But they clearly had a better grasp on how to maintain social lives through adulthood and how to build communities. They had people over. Many Millennials and members of Gen Z take it for granted that seeing friends requires going to a third place and buying an expensive meal. My argument is that we were wrong to normalize that behavior. If you think that it’s an over and above effort to invite people over and cook a few extra servings, you’re wrong. It pains me to say it, but the Boomers were right about something.

To be clear, you’re not anti-restaurant. You’re pro vibe. 
Fine dining at the higher end falls more under the category of experience spending – like a concert or a trip. Given that the price difference between fancy and middling restaurants isn’t huge³, the rational move is to go to a place with a great vibe or stay home and create one.

And don’t use size as an excuse. I live in an 850-square-foot New York City apartment and have 30+ person parties at least twice a year. Granted, I'm an edge case, but if you will it, it can happen. 

The book is also the first entertaining manual I’ve read that acknowledges not everybody is worth entertaining. I'm curious about your experience as someone who does entertain. How has it helped you understand your relationships?
My husband works in tech and, over the years, he’s brought home some men with what you might call a dire lack of interiority. One brought and ate an entire rotisserie chicken to hit his macros. That kind of modern guy can and will show up, which is why I recommend coming up with some games or activities. Booze never hurts either. But also, it’s okay. They can’t all be winners.

We are losing, in some ways, that basic internal divining rod of etiquette. Not everyone knows how to be present in society. I think when you’re hosting, you put yourself out there and find out who will meet you halfway. 

Your version of meeting halfway is a bit sexy. You definitely describe trying to create a sort of adults-only permissive atmosphere – albeit without hosting a swinger’s party. How do you calibrate that effort to be romantic toward people you don’t want to sleep with?
I always remember this line from Fleabag where Kristin Scott Thomas says that when you go into a party at her age there's no real danger anymore. There's no chance you might kiss someone or whatever. You want to create a bit of that youthful danger for people who aren’t in that stage of life anymore. People like to feel attractive and you want to create a silly, adventurous environment in which they get that feeling. 

It’s tempting to fall into that trap where you think: “If my friends love me, I shouldn’t have to make an effort.” It seems like you’re pushing back very hard on that idea of intimacy as an excuse to not try.
There’s that old wisdom that people are, as a rule, least considerate to those closest to them. I think that’s right and that we put romantic love on such a high pedestal that we wind up devaluing platonic relationships. Your friends deserve the best version of you. They should be the keepers of the best version of you and you of them. The best version of us is normally the version that’s trying.

One of the things that becomes clear is that the best version of you, Chelsea Fagan, is pretty whimsical. How do you think about that specific kind of socially acceptable, quasi-sophisticated silliness?
There’s this group of 60-year-old and older gay men in the Hudson Valley that are sort of the keepers of the good antiques and their houses are, generally speaking, really beautiful, but also funny. It’s a subcultural thing, but it’s also, I think, because these are men that lived through the AIDS crisis. They lost so many friends and lovers. So when they celebrate, they take whimsy and beauty and connectedness and aliveness seriously. But the result isn’t seriousness.⁴ 

I think deep down, we know that what humans really crave is a feeling that is sort of a little bit naughty, a little bit whimsical. There’s this idea that dinner partiers are this inherently stuffy thing, but deep down I think we know that’s wrong. It just takes a bit of courage to buck that.

I feel like political discussions can become a sort of anti-whimsy. Do you have a strong feeling about politics at the table? It feels unavoidable these days, but a lot of those conversations are more rooted in performance than anyone saying anything interesting.
I’m actually a fan of political conversation at the dinner party, but I do think it can become a circle jerk. So I try to push toward topics that sit downstream from or adjacent to politics – political, but not American politics – in order to avoid inciting earnest, relentless agreement. My husband is French so maybe I’ll try to get people to talk about French politics. I grew up lower income in the South and I think outsiders – I guess I am one in Manhattan – have a lot to offer if they’re given space. They can talk about their experience while making it a bit less about themselves.. 

Alright, last question: You’re going to a party. People know you’re an expert on entertaining so they’re watching you a bit. What do you bring?
So I always like to bring two things, one for the party, one for the host. I’m a fan of bringing an interesting liqueur or a nice digestif for the party and something the host might use in the future: cute cocktail skewers or things like that. That said, the big winner is always bringing pastries for the next morning's breakfast.

[2] It is true that AI has probably created a lot of value for investors by promising to lower overhead. The job killing story – ostensibly negative for AI companies – is, on some level, a marketing coup because it implies that the technology has a power it hasn’t really demonstrated to date.

[3] Chelsea is to polite to say it outright so I’ll just do it: Going out for a kinda nice meal is dumb. Go big or go home and go big.

[4] Anyone with a man like this in their life knows exactly what Chelsea is describing. It’s a feeling – a very cozy one at that.