About President Obama. Though I made that first “Loving” list before I’d ever heard of him, if you had told me back in 2003 that the United States would soon have a black president and that president would be the son of a white woman, I wouldn’t have batted an eyelash. Mr. Obama, born in 1961, is at the leading edge of the “generation” I was looking to define, and the journey that led to his becoming the first black president was impossible to separate from his adjacency to whiteness. Ta-Nehisi Coates probably put it best in his January 2017 Atlantic magazine article “My President Was Black.” He explained how Mr. Obama’s direct connection to, and intimate familiarity with, white people — his mother, Ann Dunham, and her parents — helped fuel his sense of possibility, of not only who and what he could be but also what he could mean to others.

“The first white people he ever knew, the ones who raised him, were decent in a way that few black people of that era experienced,” Mr. Coates wrote.“Obama’s early positive interactions with his white family members gave him a fundamentally different outlook toward the wider world than most blacks of the 1960s had.” He also noted that Mr. Obama’s lens, “born of literally relating to whites, allowed Obama to imagine that he could be the country’s first black president.”

There are other firsts within the Loving generation. Like Halle Berry (1966), the first black woman to win a best actress Oscar. And Amy DuBois Barnett (1974), the first black woman to run a major mainstream consumer magazine. And Jordan Peele (1979), the first black writer-director whose debut movie earned more than $100 million at the box office. And let’s not forget Meghan Markle (1981), who is about to become the first black British royal (of the 21st century, that is).

I used to wonder whether people like Ms. Berry, or others in my particular and uniquely American generation, had ever made this specific observation, and been disturbed by it. It was a lot to come to terms with. I knew, even as a young adult, that I moved among and around white people with relative ease, in a way that my blackness — and my own perception and self-consciousness of it — wasn’t at the foreground. What I didn’t know is whether that had something, or everything, to do with what I’d accomplished.

Turns out, I was not alone. Erin Cloud, a public defender in the South Bronx, has similar concerns. “At my job, there’s actually a lot of biracial people that are in more leadership opportunities, and I think about that. I’m like, ‘Well, is that because there’s something about their whiteness and our whiteness that is giving us space to communicate and that’s why we’re getting promotions and why we’re moving forward?” she said. “I am a black woman. I see myself as a black woman, but I also have to be honest. I love my mother. I can’t say for many of my black friends that they deeply, intimately, without any bounds love a white person.”

Ms. Cloud was born to a black man and a white woman who met in the late 1970s while the latter was attending Morgan State University, a historically black college. Erin came along in 1983. She is one of more than a dozen participants in a new documentary series called “The Loving Generation,” which I executive produced for the website Topic with Ezra Edelman (1974). It’s directed by Lacey Schwartz (1977), a filmmaker who explored her own black and biracial identity in the 2014 documentary feature “Little White Lie,” and Mehret Mandefro.

Mat Johnson, who wrote the 2015 novel “Loving Day” and is the son of a black mother and a white father, was also interviewed for the documentary. Though he is quick to acknowledge that members of our generation enjoy access to elements of white privilege — what he calls “off-white adjacency” — he explains it’s important to take other factors into consideration when considering the successes of the Loving generation, namely economic class and the outsider-overachiever dynamic. “Particularly with those of us who are black-identified, we get into the mode of trying to overcompensate to fit in and be accepted,” he told me.