If Chelsea Handler’s Paying, You Better Perform Pleasantness 

Family vacation can make even the most level-headed people go a little batty, but there are a few easy cures for that: take a walk; feign a stomachache and take to bed; argue over dinner and make up over dessert. Chelsea Handler—never one to follow the crowd, to be fair—has chosen an entirely different route: apparently keep everything bottled up during the trip, send a self-righteous email about things that bothered you an undetermined amount of time later, publish that email in your book, get someone to stylize it for Instagram, and re-publish it in a nine-slide carousel a year after your book comes out. Maybe that’s not her typical way of dealing with family tension, but it’s exactly what she did last week. 

The post was addressed “To All My Nuggets” (which, from context, appears to mean her nieces and nephews, of which she has eight), featured her 2025 book’s title—I’ll Have What She’s Having—at the bottom of each slide, and was captioned, “It’s family vacation season, which means it’s time to reread the rules. If you want to vacation with me, these are the rules.” Each slide included two or three bolded lines, though it’s unclear if there was any particular metric determining what was emphasized, or whether the emphasis appeared in the initial email. (That information may have been available in her book, but I have minimal willingness to read additional Handler copy, I’m sorry.) Handler’s notes (or, more accurately, complaints) pertain to her “house in L.A., or Mallorca, [Martha’s] Vineyard, or wherever we happen to be vacationing.” 

 

 

 

 

 

 

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The bolded phrases are initially just about basic human decency, and I suspect this is intentional to get everyone on her side. On her household staff: “You do need to acknowledge their existence out of decency and respect,” and “I treat my employees like family and I expect you to do the same.” (That being said, Handler is in this very email laying out some bizarre guidelines for what her family is allowed to do on vacation—more on that in a sec—so “like family” is not exactly conjuring a warm, fuzzy image.) More broadly: “It is the nice and decent thing to do, to be conscientious of others who are also on the vacation with you.” A) Sure but duh, B) that’s a comma splice. 

After starting out with some extremely reasonable comments—which should have been delivered in person, at the moment when the behavior bothered her, rather than in a passive aggressive email after the fact that she then published to her 5.4 million followers—Handler immediately pivots away from normal complaints. Being conscientious to Handler means “not finishing bottles of Belvedere that I purchased, or ginger ale I flew with across the country, that they don’t sell on the Vineyard.” It means following her instruction to “not consume copious amounts of alcohol on multiple occasions”—so you get to be a little tipsy exactly once on vacation, otherwise it’s “not a way to get invited back.” In one line that might make sense in the context of private family correspondence but seems extremely sexist to a public audience, she says, “Girls—Be kind and thoughtful to my guests. Do not roll your eyes repeatedly or even, ever.” Boys, I guess you can do whatever the fuck you want! (Also, that’s another comma splice.)

She then spends two paragraphs chastising her “nuggets” for their moods, before abruptly saying, “A good rule of thumb as a guest is to never finish something. When I make a pitcher of margaritas, don’t finish that pitcher unless you’re willing to make another.” This to me is honestly the most insane demand of all—sometimes a pitcher of margs gets finished! Do you really want everyone to avoid taking the last four sips and letting that shit get watered down with melted ice?? Ah but this is but a fleeting notion; she then pivots immediately back to commenting on their manners: “I need everyone to say please and thank you at every opportunity, and more often.”

I really could go on; it is a rich, poorly edited text. The basis of her frustration seems somewhat legitimate—hanging around moody teens is not my ideal form of vacation. That being said, I’m not the rich aunt who’s invited said moody teens on vacation and then gotten mad at them for being moody teens. At one point, she asks them to consider, “What sort of pleasantness are you planning to bring on vacation?” You gotta perform cheerfulness, I guess, or else Auntie Chelsea’s keeping the door to the vacation home locked up tight.

Handler is seemingly justifying her public shaming because she feels taken advantage of—but also, girl, no one is forcing you to pay for your entire family to go on vacation! This seems to be a widespread problem among the 1% though; her rich and famous friends all loooooved the post, with Reese Witherspoon commenting “Right on,” Denise Richards saying she’s “saving this,” and Chrissy Teigen going with a characteristically over the top “HOOOOOOOOOOOOBOY!!!!!” I guess wealthy women need to get better at setting boundaries with their families???

Last year, while promoting her book, she told Jimmy Kimmel that they’ve been on a family vacation since she sent the email (which I assume means she sent it in 2024 at the latest), so it seems things worked out okay in the end. But I really would love to know what her nieces and nephews have to say about their aunt airing their business in public years after the fact!

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