How to host the perfect game night, according to the woman who plans Questlove’s star-studded ones

The key to hosting a game night so good it brings out Taylor Swift’s competitive side? Overprepare, according to Cathy Rong, Questlove’s chief of staff and the woman behind his viral star-studded board game bashes.

Rong can spend up to three months in advance planning semi-regular game nights for the Roots frontman, documentarian, and sandwich entrepreneur, who started hosting the parties as a way for his famous friends to unwind.

The prep is for good reason: Questlove’s rotation of celebrity guests include Swift and fellow Philly luminary Quinta Brunson, as well as Channing Tatum, Trevor Noah, Lin-Manuel Miranda, John Legend, and Chrissy Teigen, among others.

The parties balance high- and lowbrow fun. The most recent game night Rong planned was just before the Met Gala, and the dress code called for sweat suits. And last July, Brunson and Questlove teamed up to host one in Los Angeles with an ice cream truck, Scrabble, and a Game of Thrones-themed version of Monopoly.

“Game Night has always been my thing,” Questlove captioned an October 2023 Instagram post. “Even 10 years ago.”

They’ve also always been Rong’s, who grew up in California before moving to New York City to attend New York University. After working as an executive assistant at Gary Vaynerchuck’s VaynerMedia and Complex, Questlove hired Rong in 2022 to help him juggle his various creative projects. Outside of work, she plays Catan with her friends, obsesses over gaming tables, and has a closet shelf dedicated just to tabletop games.

Obsessing over board games with her boss, Rong told The Inquirer, was never in the job description.

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“It became kind of a passion project for both of us, but it was definitely not part of my initial scope of work,” Rong, 28, said with a giggle over Google Meet. “I enjoy bringing people together.”

Admittedly the game nights Rong plans for Questlove are more curated than casual with a strict no-phones policy and an on-site photographer. Previous swag bags have included upscale dice, silk pillowcases, and custom Uno boosters.

None of those, said Rong, are required for a good time, but there are still some guidelines for taking game night from a dud to a slam dunk.

“Sitting at a table and starting with the same set of rules kind of equalizes everyone. There’s no ego,” said Rong. “I think of [game nights] as a way to be intentional about setting aside time for fun.”

Looking to level up your game nights? Here are Rong’s four tips for planning a game night so good a celebrity might show up.

A good game night should feel like a choose-your-own-adventure book, according to Rong. In other words, give your guests options.

Rong prefers long-form games like Catan and Wingspan (a cozy-yet-competitive strategy card game where you collect birds to build the best wildlife preserve), but acknowledges that most people prefer something you can win quickly.

“Not everyone has the patience to sit through Catan and pick it up,” Rong said. “Some people prefer something snappier and faster that can take, like, two minutes a round.”

Rong recommends offering a mix of games. Recent hits at her and Questlove’s parties have been Tetris-adjacent puzzle game Blokus and Uno, which Questlove told Hot Ones host Sean Evans he uses as a “personality tester” for game night newbies.

Another unexpected game night hit: Speak Out, which asks teams to guess what words or phrases players are saying through a mouthpiece and is a favorite of game night regular Chrissy Teigen. “Uno still reigns supreme but Speak Out is up there if you are ok with people you have never met seeing you drool,” she wrote in a 2023 Instagram post.

“That was unexpected because [Speak Out] had never been picked up at one of these games nights before,” said Rong. “It was a nice departure from the mainstream.”

The takeaway, it seems, is to never prematurely prune your collection.

What comes first: The chicken or the egg, or — er — the games or the guest list?

For Rong, the games in circulation determine how many people she invites since some — like Catan or mahjong — require a specific amount of players or extra space. And while some people like to spectate, game night hosts should not go in with the expectation that people will be OK sitting out. The point, after all, is to play.

“The number of people does mater,” Rong said, deadpan.

Rong also recommends circulating YouTube tutorials of lesser-known games ahead of time to level the playing field. It goes without saying that board game haters — and sore losers — don’t make the cut.

“Beyond personalities, a love of gaming is the first prerequisite” for being invited to her and Questlove’s game nights, said Rong, not being a celebrity. Maybe my invite got lost in the mail?

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While some hardcore gamers are anti-finger foods (dust! high-touch surfaces!), Rong can’t imagine serving anything else at her gatherings.

“I mean, something like soup isn’t going to go over well,” Rong said.

For the game nights she plans, Rong enjoys a mix of novelty and self-serve foods, like pizza cupcakes from Whole Foods, ice cream, and cereal bars. At Questlove’s most recent game night, Rong tapped Bronx-born culinary team Ghetto Gastro to create a special menu of takeout-style finger foods, including oxtail patty burgers, fried chicken topped with caviar, and matcha-swirled Swiss rolls.

Rong’s personal game nights are a more “casual” affair sans swag bags, but she does relish curating the party favors for Questlove’s gatherings. The best goodies, she explained, elevate the gaming experience. Once, Rong said, she commissioned a custom +25 Uno card themed after her boss for guests.

Though Rong describes herself as “in the middle” on the casual-competitive spectrum, she said that some trash talk and low-stakes rivalry can be a good thing.

Actually, Rong said, competition is part of what makes her and Questlove’s game nights so fun.

Reading-born Swift, for example, is a known Uno hustler who Questlove said takes the card game “to levels of excitement that I didn’t know one could do.” Rong said comedian Trevor Noah is similar, while actress Stephanie Hsu runs the mahjong table. “She wins like basically every game.”

“It gets tiring to go to one PR event after another ... this is just like a hobby club,” Rong said. “There’s a huge competitive streak in the room. There’s trash talk, there’s spectators. Everyone lets their guard down.”