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Personal Perspectives

A White Woman on a Black Vacation

I learned a lot about race—and life—in an uncomfortable but incredible place.

Key points

  • Is it culturally humble to put ourselves in spaces dominated by another race?
  • How can we pay it forward if we do?
  • Here's one author's personal, lived experience.
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I’ve had a hard crush on Stevie Wonder since forever. As a pre-pubescent teen, I penned my lifetime one-and-only fan letter. “I’m sorry you won’t be able to read this, but…” That was over 40 years ago. Closer to 50 (let’s be honest).

Early last year, I asked Alexa about Stevie. “Ziggy (my gender-neutral echo’s name), play Stevie Wonder from 1974.” Riding the wave of smooth, synthed, can’t-help-but-move “You Haven’t Done Nothin’” and “Boogie On Reggae Woman,” I absently googled if Stevie was performing anywhere. A one-week, Caribbean, all-inclusive, Black resort vacation sprung up. Curious, I clicked. “SOLD OUT SOLD OUT SOLD OUT” the screen blared. I turned away, back to work.

Then, I found myself back on the webpage. Trip profits benefitted Historically Black College and University (HBCU) scholarships. I filled out an online form to be notified of cancellations, telling myself to let it go. Days later, I hadn’t received so much as a robo-email acknowledging my inquiry. I gnawed thoughts about the trip like my tongue on a rough edge of a tooth.

I’d seen a phone number on that website, hadn’t I?

I called it. They won’t answer, I told myself. And if they do, the trip is sold out. If there’s room, and this works, I can consider it. If not, time to let go.

A southern-accented woman answered the first ring.

“Are there openings for the trip?” I blurted. “And is Stevie really playing?”

“Yes, there are. And he certainly is!”

I was nervous, going alone. I texted close friends and family, all white. They giggled. “I can’t believe you’re doing this!" they effused, “And good for you!” Then they declined to join. My daughters couldn’t leave work, and thought this was cultural appropriation (they had a point). My son-in-law, who is Black, needed to cover someone else’s vacation. I’d feel safer going with him, I admitted.

I exchanged several calls with the woman from the website. I was a pain in the proverbial tuchus, but she seemed unconcerned. I needed a balcony, for fresh air. I wanted to be higher up, for quiet. I’m old, privileged, white; even if I don’t always feel white, because I’m Jewish. I pass, and my privilege is evident every time I walk into an upper-crust boutique, trending Portland café, airport, or classroom. Especially living in what is still known as the whitest city in America. I packed plenty of sunscreen, knowing it would be a commodity most wouldn’t need.

The hotel lobby buzzed, a packed sea of chatting, animated, vacation-ready people in loose, colorful clothes. None of them white. I stopped, reaching for my phone like some security blanket, snapping a photo and texting my daughters. “I’m afraid I shouldn’t be doing this and it’s totally not cultural humility,” I wrote. They didn’t respond.

You knew it would be like this, I told myself. Duh! This exact experience and even your discomfort right now are a big reason you are here. Breathe.

I grew up in America. As a preschooler, my father worked on civil rights in the Jewish community, but my mom, professing equality, anxiously insisted, “Lock your doors!” when we drove through inner-city neighborhoods.

A woman behind me in the lobby smiled. “Where are you from?” she asked. My shoulders relaxed as we chatted. At the first meal, I smiled when people caught my eye. Most smiled back. Some averted their gaze.

Oh shit, I thought. Just by being here, I’m triggering. So not okay. What made me think I could—

Or maybe some people aren’t smiley?

Or maybe the people that are smiling are reflexively trying to avoid trouble—prioritizing my white comfort over their own?

Shit!

I considered not meeting peoples’ gaze, looking down, going invisible (not so difficult for a 60+ -year-old female in America), but I forced myself. Just try, I thought. This is so not about you. Be a good ally: respectful, humble, supportive.

As I bound up and down stairs, everyone piped “Good morning!” or “Hi!” to the point I began doing it too. I worried people’s friendliness came as reflex—my skin a beacon to provoke best behavior. The thought sickened. Then I noticed everyone greeting everyone, everywhere, like friends or family—the pool, the bar, the lobby, the paths. Maybe Black people are just nicer. Definitely more direct. What a pleasure, I caught myself thinking. Then: There it is, systemic, internalized racism: “Maybe Black people are…” As if Black people are any one thing, a monolith. No.

“If only we could be this nice and friendly to everyone, all the time,” one person posted on the Facebook page dedicated to this trip. Friendliness was up a notch for everyone—we were on vacation, after all. But it felt warmer, more intimate than trips I’d been on with hegemonic white groups—resorts, business, tours—anything.

“Is someone sitting here?” several people asked at meals, seeing me alone. One was an HBCU administrator. Another, the husband of a C-suite executive. All around, it felt normal to be curious. “Can I ask why you came?” a few asked, their directness a relaxing relief.

“I came for Stevie,” I admitted. “And to support HBCUs.” Loving Stevie seemed universal. No one so much as intimated it was inappropriate I chose to be there; but maybe they were privileging my comfort. “Everyone is so warm,” I’d say. “Except, maybe I’m imagining, but some avert their eyes—”

“That’s on them,” my meal mates suggested.

“I want to be respectful though,” I insisted. “I don’t want to trigger people by being here. If that’s the case, I shouldn’t have come.”

I tried not to expect appeasement or reassurance—white fragility is exactly that, wanting to be told what’s most comfortable for me. I wanted the truth.

And then, toward the end of the week, Stevie.

I joined a line outside the venue hours early, at least a hundred people ahead of me. I brought a book but never cracked it, talking instead to a pharmacist about empowering patients with chronic illness. When the doors opened, I strode to the fourth row, inner aisle, close enough to see Stevie, right down to his shoes and socks.

He strode onstage arm-in-arm with his assistant and stood, wearing a bright red suit with a rainbow appliqued on the back, the crowd roaring with pleasure. Silent, he sat down, playing the intro to “Close Your Eyes,” dancing his hands over the keys. Quietly, he spoke. “I love you,” he said softly, then began to sing.

“Family,” he said mid-set, “we don’t have much time together, so we have some decisions to make. Do you want me to play the song that starts like this—?” he riffed a couple notes of “You and I,” teasing and laughing. “Or this—” he played the first phrase of “Ribbon in the Sky.”

“Ok, here’s what we’re going to do,” he grinned. “I like to keep it fair. We’ll do a little bit of ‘You and I’ and a little’ bit of ‘Ribbon in the Sky.’ Because you can’t always have it all the way you want. You have a debate you want to be in? Then you should get up and vote! Ya feel me?” He launched into his number.

We heard “Signed, Sealed, Delivered,” “Superstition,” “Sir Duke,” “Higher Ground,” “Hotter than July,” “Overjoyed,” and so much more.

“We can’t put it in the hands of fate,” he paused. “You can put it in the hands of faith, but you can’t put it in the hands of fate. If we want change for the good, for everybody, then we do it. I say to my kids, ‘I know you’ve been taught to “put it in God’s hands.” But you know what? God has given you hands. Use your hands to make a difference…' You feeling it?”

We were. We roared.

“Then I’ll tell you I love you, and let’s get this thing together!” he yelled. “Put your hands together and clap. Put your hands together and clap!” He guided women and men to sing alternate lines of “If You Really Love Me,” laughing at the intimacy he’d created. He dedicated a song to Tina Turner “and her greatness,” as she had just died, and promised every penny of his proceeds would be sent to HBCUs. “Are y’all good?” he asked. We were.

Way too soon, it was over.

I miss it. All of it. And yes, I do love you, Stevie. Thank you for stretching me, throughout my life. Forgive me for gatecrashing; I hope I did a creditable, respectful job. I will take the memories and lessons with me, forever.

Signed, sealed, delivered: I’m yours.

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