reckoning with a reckoning

Guilty Parties

Two entrepreneurs have built a business dredging up white women’s shame.

Photo: Jesus Trillo Lago/Getty Images/iStockphoto
Photo: Jesus Trillo Lago/Getty Images/iStockphoto

Were White Fragility to be adapted as reality TV, the result might look something like this: A collection of affluent white women, equipped with varying degrees of vanity and self-delusion, gather at a well-appointed dinner table. There, they face down a pair of unsparing judges prepared to see right through them. Who’s racist? Time to find out. White wine flows; white women admit shameful secrets. They get squirmy; they get angry; they turn on each other. If one of them starts to cry, she has to leave. She will find tissues in the designated crying room.

The Bravo version of Robin DiAngelo, in other words, might look a bit like Race2Dinner. Begun in 2019 by Regina Jackson and Saira Rao, Race2Dinner gathers groups of eight white women at the home of a white host, where Jackson and Rao facilitate a discussion about race over dinner. Early in the evening, for example, they will often ask the white women whether they would prefer to trade places with Jackson (who is Black) or Rao (who is Indian American). The women will almost uniformly choose Rao. “So they know,” Rao said. “They know the entire ecosystem.” The idea is to bring such submerged racial judgments to light, however uncomfortable this might make the white women. Jackson and Rao ask guests to describe racist things they’ve recently done and press them on any evasions. Often the examples that emerge involve silence: failing to speak up or intervene. Sometimes they consist of thoughts or feelings: assuming that the Black teens pulled over in a white neighborhood must have been doing something wrong. Sometimes the guests struggle to think of what to say. “Not knowing is classic white behavior,” Rao told me. “You don’t know, because it would ruin your entire image of being the perfect, nice white lady. I’m sure you’re intimately familiar with this, being a white woman.”

Race2Dinner participants sign up for something that promises to be painful, unsightly, and yet transformative, like a chemical peel for the soul. “Interested in hosting a dinner?” asks the Race2Dinner website in red text superimposed on a shattered china plate. “Click here to smash your white fragility.” Guests used to be asked to read White Fragility, but no more. For one thing, Rao said, “we definitely don’t want to put another dollar in Robin DiAngelo’s pocket.” For another, among prospective customers, pretty much everyone has already read it.

When they first started out, they charged $2,500 per dinner, to be covered by the host or divided among her guests.

“That’s peanuts,” Jackson told me when we spoke over Zoom. “People pay more than that to go to a yoga conference.”

“To a yoga class!” Rao said. “In New York City, that’s like a yoga class — with, like, a green juice on the side.”

Their business model, unsurprisingly, attracted attention. In February 2020, a Guardian article on their dinners made the rounds online, inspiring umbrage and hilarity across the political spectrum. “White Women Paying $2.5K for a Dinner to Learn How They’re Racist,” read the headline on a New York Post rehash of the report, cutting right to the chase. Jackson and Rao, meanwhile, received an influx of new inquiries about their service and signed a deal to write a book called White Women: Everything You Already Know About Your Own Racism and How to Do Better. They also raised the fee for each dinner to $5,000.

While the pandemic scuttled planning for events in San Francisco, New York, and D.C., a new wave of interest soon arrived amid the protests that followed George Floyd’s murder. Lisa Bond serves as Race2-Dinner’s “resident white woman”; Jackson and Rao hired her to help organize events after she hosted her own dinner two years ago. (Bond had initially balked at the cost, but after seeing a post from Rao and Jackson about how many white women balked at the cost, she resolved not to be like the others.) Last summer, Bond said, she fielded some 300 emails in a three-month period and had nearly 100 follow-up phone calls of 30 or 45 minutes each. Of those, three women proceeded to book an event. “We get excuse after excuse after excuse,” Bond said. “It’s typical white-women fashion.”

Jackson and Rao, who live in Denver, met in 2018, when Rao ran an underdog primary campaign against Democratic congresswoman Diana DeGette — “literally the patron saint of toxic white womanhood,” Rao said. Before running for Congress, Rao had been a lawyer at a Wall Street firm. She left after publishing Chambermaid, a roman à clef in the mold of The Devil Wears Prada about her time clerking for a federal judge. (“Funny and charming,” said Gary Shteyngart of Chambermaid. “I haven’t read it. I don’t intend to. I really don’t care. Okay?” said Rao’s former boss.) Following the 2016 election, Rao had grown frustrated with the reluctance of her mostly white friends to talk about race. Jackson, who’d spent her career at AT&T before starting a real-estate business, appreciated Rao’s willingness to speak frankly even when it made white people upset. The two became friends. Race2Dinner took shape after a white friend of Jackson’s — a former friend, Jackson stresses now — told her that she was “done with Saira” because of the way Rao talked about white people. The friend was hoping that Jackson could help arrange for her to have lunch with Rao and discuss this in person. Rao agreed to a meeting on the condition that Jackson would join her and that the woman would invite a group of her white friends. This was effectively the first Race2Dinner.

Since then, Jackson and Rao’s methods have evolved: In the past, they did more of the talking; now, they focus on drawing the guests out. But something of that first woman’s muddled impulses — to object but also to have lunch — seems to persist among those who have followed. “It’s so funny how many of them want to be our friends,” Rao said. “We’re like, We don’t want to be your friends. Be your own friends! 

Since last summer, in Jackson and Rao’s view, things have and have not changed among their customers. “There’s more acknowledgment of, Yes, we create this, and, Yes, we need to engage,” Jackson said. “There’s a lot of facility around language that in some ways is more dangerous,” Rao said. “People have words. The actions are not there.” Still, they felt that the first Race2-Dinner they conducted after the protests had been a success. It was a Zoom with the white employees of SheEO, a network of investors who fund businesses led by women. SheEO had invested in Rao’s previous business — a diversity-focused children’s-book company she founded with one of her UVA sorority sisters — and Rao was surprised to hear from SheEO now. A few years back, SheEO founder Vicki Saunders had made what Rao called an “extremely, extremely toxic white feminist” reply to one of her Facebook posts about race. “She was just like, ‘You’re being hateful. You’re being divisive,’ ” Rao said. “It’s white-lady-speak.” Saunders remembers this differently: She called Rao’s description “completely inaccurate” and thinks she said something like, “Hey, if you’re trying to be effective, XYZ, maybe you want to try this.” In any case, Rao then unfriended her.

Saunders booked her team’s Race2Dinner after a Black entrepreneur SheEO had funded asked how the organization would be responding to last summer’s events. “I’m very much action oriented,” Saunders said. “I’m not a person who’s going to post a list of ‘Here’s six things you should read about whatever’ and ‘Here are the four layers of white supremacy.’ ” Her colleagues, she said, are “a fairly courageous bunch,” but “hearts were racing” nonetheless. As introductions were made and everyone was asked about their racism, Saunders volunteered to speak first. To Rao’s great surprise, Saunders described their Facebook exchange from years before. “She set the tone,” Rao said. The women from SheEO “really acknowledged some hard stuff,” Jackson said. “You could tell that people were embarrassed. That’s why people don’t like to acknowledge their racism — because it’s embarrassing.” Despite Race2Dinner’s usual no-crying policy, there were tears. “It was true vulnerability and honesty,” Bond said. Afterward, SheEO formed a racial-justice working group that continues to meet regularly and this year funded a cohort of entrepreneurs that was 100 percent Black. (Saunders has also “gone all over social media to tell people to do Race2Dinners,” Rao said.)

Generally speaking, however, the remote orchestration of true vulnerability is a challenge. “The Zooms do not work nearly as well,” Rao said. “So much of this is eye contact, body language — actually getting to work together in a room over food.” The sense of social obligation that a dinner party creates — to remain at the table, keep talking, stay engaged — does not necessarily translate onscreen. Last fall, shortly before the election, they did a Zoom with a group of women from a wealthy Connecticut enclave that Jackson and Rao agreed was one of their worst events yet. Rao: “They were apathetic. They were bored. They were openly box–checking. There was some eye-rolling.” The Connecticut women were all gathered on one screen while Rao and Jackson called in from Denver. “It almost felt like they were together ganging up against us,” said Rao. “They could do their united thing in opposition,” Jackson said. The undercurrent of defensiveness that competes with guests’ desire for approval predominated in this case. “They wanted to know, over and over and over again, ‘What is cultural appropriation? Give us definitions,’ ” Rao said. “And any definition we gave, they would combat us and be like, ‘Well, no, that’s not it.’ ”

One of the past year’s few in-person dinners took place three days after the attack on the Capitol. Rao said that one woman — “the only woman in the group who seemed remotely willing to do this work, period” — had a question at the end of the evening. She looked at Jackson, and she looked at Rao, “and she goes, ‘Do you see any difference between us and the people that stormed the Capitol?’ And we both said, ‘No.’ ” The assembled women, a group of Colorado business and nonprofit leaders, “lost their entire minds,” Rao recalled. “So this notion of not all white people, not all white women — that is completely unchanged.”

Even so, they had some sense their message is being heard. Often Jackson and Rao receive emails and texts from former guests: They were walking down the street, they report, and they didn’t cross when they saw a Black man coming. They were at a dinner party, and someone said something about a “ghetto” school, and they pointed out that it was a racist thing to say. “If even one woman from one of these dinners makes life slightly less toxic, even one day at work or at one dinner party, then our work is done,” Rao said. “And we’re absolutely seeing that — otherwise we wouldn’t still be doing this.”

“We want people to, No. 1, call a thing a thing,” Jackson said. “Quit pretending like you don’t see shit, and start using your voice and your power to make change. What’s the worst thing that’s gonna happen to you? If you see a white person saying something derogatory or doing something derogatory, and you interrupt it, what’s the worst thing that’s going to happen to you? I mean, really think about it.”

For white women who wish to continue the work begun at Race2Dinner (and for those who might not wish to attend), they have launched a new program called Race2-Community. An eight-week seminar led by Bond, it costs $750 and focuses on whiteness specifically. “The actual work is for you to deconstruct the things within you: whiteness,” Rao said. “Whiteness harms people of color, but worry about yourself. Stop worrying about us — that’s paternalistic, too.” Bond echoed this sentiment. “This idea that we, as white people, need to go out and make these big external actions — that’s just white supremacy,” she said. “This internal work is the hard work; it’s the work that never ends.”

They see the deconstruction of whiteness as a prerequisite for true anti-racist work. Jackson explained, “Until you deal with your inner stuff — until you can say, ‘I’m coming from a place where I recognize that I have these thoughts, and I’m working on it’ — everything else is performing.”

More From This Series

Eavesdropping on $5,000 Anti-Racist Dinner Parties