Alexandra Kennedy was on the inside looking out. For much of the evening, streams of Polo-clad students had sped east across the Princeton campus, flooding Prospect Avenue and breaking in waves against the row of imposing mansions, called eating clubs, where most upperclassmen "take their meals"—and where nearly all undergrads go for their regular dose of dancing, drinking and hooking up. Now hundreds filled Ivy, the oldest of the clubs. Among them was Kennedy. After a season spent clamoring at the door for admission like the rest of the rabble, Kennedy, a svelte, self-assured African-American sophomore with straight, shoulder-length hair and a fondness for cable-knit sweaters, had recently emerged from Ivy's Darwinian "bicker" process—a prim rendition of rush—as one of the chosen few: a member of the club.

It was a natural next step in the Kennedy family story. Alex's father, Henry Kennedy Jr., the son of Southern blacks, arrived at Princeton in 1966 from a middling Washington, D.C., public school. Now his daughter had joined a club where all-black waiters had, until recently, served an all-white membership—a place where, as a guest, her own father had "felt very uncomfortable."

Still, change creates its own complications. As a bouncer restrained the hopefuls and '80s rock blared on the sound system, Kennedy resolved to put her new status to use. Tonight, she decided, she would reach across Ivy's intimidating threshold and distribute her share of admission passes to a select group of beneficiaries: "the black people." "I thought about it," she says. "I know how hard it is for African-Americans to feel welcome in these clubs." But as Kennedy ushered the first lucky recipients inside, a cold voice cut through the crowd. "I was literally on my knees signing passes," she recalls, "and this black girl waiting outside was like"—Kennedy adopts a deeper, mocking tone—" 'This club's racist. They're not letting us in because we're black'." She rolls her eyes. "And for me, I'm like, 'I am standing out here trying to get you in. This isn't a race thing. It's a pass thing'."

Two elite African-Americans on either side of a velvet rope: one feeling excluded, the other exhausted. Such is life on the cutting edge of "post-racial" America, where race isn't supposed to matter anymore. Except when it does.

Linked in the public consciousness to Barack Obama, the term "post-racial" has now expanded to encompass the era his election has ushered in. But in the real world, post-racialism is something of a mirage. Detroit is not post-racial. Neither is Congress, nor Wall Street, nor prime-time TV. Black people pretty much refuse to utter the word, Obama included. For most Americans, it's little more than a convenient cable-news catchphrase.

It's only at places like Princeton—selective, self-sufficient institutions that have spent many years (and millions of dollars) cultivating climate-controlled biospheres of diversity—that anything even remotely resembling a post-racial America is supposed to have taken shape. A quarter century ago, the future Michelle Obama, then a Princeton senior, confessed that her time as a Tiger had left her feeling "black first and a student second"—the result, she wrote, of "a white cultural and social structure that will only allow me to remain on the periphery of society … never becoming a full participant." But decades of progress have proved that prediction wrong, propelling Michelle to the White House and creating for her descendants a university that boasts 17 tenured black professors, an ambitious new Center for African American Studies and a black population larger and more integrated than the one she left behind. In 1981, 18 percent of her fellow freshmen were minorities. Last year that number hit 39 percent. Back then the university had perhaps 1,000 black alumni; now it's more like 4,000. At Princeton, the periphery has become the mainstream.

But living in a post-racial bubble—a place that expects everyone to have gotten over race—isn't as easy as it looks, especially if you happen to be black. Last month NEWSWEEK asked two of the first multigenerational African-American families to pass through Princeton—Henry Kennedy, '70, and Alex Kennedy, '09; Jerome Davis, '71, and Kamille Davis, '05—to map out, in miniature, how life on the front lines of racial progress has changed over the past four decades. The contrast was stark. The fathers—among the first generation of black students accepted into the upper echelons of society—arrived at a time of political unrest and, whether they engaged or retreated, drew strength from their common challenges. But their daughters—among the first African-Americans to enter Princeton with the same advantages as the most privileged of their white peers—have struggled to satisfy the competing demands of the black world they've inherited and the white world they inhabit. In the Age of Obama, the old battle lines may be disappearing. But in a certain sense, that's only made it harder for the next generation of black elites to know where they stand.

Jerome Davis's standing was never in doubt. On a Thursday night in October 1968, Davis's sophomore year, a student named Reginald Peniston called in a noise complaint against the raucous Rockefeller Suite, then accompanied police as they broke up the party. Unfortunately, Peniston was one of only about 60 black students on a campus of 3,300, while the "Rock Suite" boys, mostly football players, were white—and drunk. When Peniston left the dorm, a suite window swung open and a stream of urine rained on his head; the words "n––––r" and "black bastard" soon followed. Davis smiles as he recalls what happened next. By midnight, all the black men on campus had assembled; moments later they stormed the suite. "We … told them we would kick their f––king asses," says Davis.

The Princeton that welcomed Jerome Davis and Henry Kennedy in the late 1960s had spent much of its history on the wrong side of America's struggle with race. As the school's president from 1902 to 1910, Woodrow Wilson refused to admit blacks, informing African-American applicants by mail that "the whole temper and tradition of the place" made it "altogether inadvisable for a colored man to enter." It wasn't until 1947 that the university, forced to admit four blacks into its wartime ROTC program, became the last Ivy League school (and one of the last colleges in the North) to graduate an African-American. Even then, Princeton accepted few additional black students until Davis, Kennedy and their contemporaries arrived two decades later.

With fewer than 20 African-Americans per class, "fitting in" wasn't an option. (Each black student went by two names, says Davis, "so people would think there were more of us.") Instead, undergraduates like Davis and Kennedy gravitated toward one of two roles: activist or invisible man. Kennedy chose the latter. A D.C. native, he came to campus without "any expectations in terms of social life." But when his freshman roommate requested a room change to avoid living with a black student, Kennedy realized he wasn't entirely welcome. He coped by retreating into coursework. "My overwhelming sensation," he says, "was one of being 'different'."

In contrast, Davis channeled his "otherness" into political action. As leader of the Association of Black Collegians (ABC), he protested unfair university policies and assembled a mixed-race ticket for student government; it won with 60 percent of the vote. A popular figure on campus, Davis had white roommates and friends, and pursued issues that affected the entire student body. But his fondest memories involved a smaller core of black peers who partied together on weekends and all "agree[d] with the ABC's program." For Davis, the personal and the political were inextricable. "I simultaneously felt alienated from Princeton and deeply in love with it," he says.

Despite their differences, however, Davis, Kennedy and their peers were ultimately bound together by a common challenge: being "black first" in what Davis calls an "enormously white" world. At 6 a.m. on a cold March day in 1969, for example, "all but one of the black men who were currently at Princeton" participated in the takeover of a key campus building to protest the university's investments in South Africa—including Kennedy. Unthinkable today, that sense of solidarity would endure until long after Michelle Robinson (whose freshman roommate, like Kennedy's, demanded a room change) arrived on campus 12 years later. It would even become the subject of her senior thesis—a study that found, to her surprise, that black alumni identified more strongly with fellow African-Americans while at Princeton than before or after. As she recently told the school's alumni magazine, "it's a very isolating experience—period." That said, the experience seems to have been galvanizing as well. Kennedy became a university trustee and federal judge in Washington. Davis became a student-body president, Rhodes scholar, Yale Law alum and Columbia University administrator. And Michelle became first lady.

In most visible ways, race relations at Princeton have improved dramatically since the 1960s, '70s and '80s. While black students used to cluster together in self-defense, their children are active throughout the Princeton community. They room, dine and socialize with diverse groups of classmates. They even join eating clubs. But as racial polarization has declined on campus, a new dynamic has taken its place. And like their fathers, Kamille Davis and Alex Kennedy embody the two primary roles available to African-Americans in Princeton's post-racial bubble—and the confusing challenges they must now confront.

Kennedy is the insider—calm, cool, at ease. One of her earliest memories is the royal reception that greeted her at her father's 25th reunion: the daughter of "someone important," she remembers being treated like the "princess of Princeton." Then 7, she never considered another college, and when she finally arrived on campus after more than a decade at D.C.'s most prestigious private schools, she meshed effortlessly with her upper-crust peers. Soon she was declaring that she'd "love to be a CEO" and jetting to Acapulco for spring break. "I was so accepted partially because I was economically in a better situation," Kennedy says. "I was more relatable." While race may have been swept under the rug at Princeton, class, its not-so-distant cousin, still holds sway. So it's no wonder that Alex says she's been "more than included"—a black girl who "never ... felt like I was the 'black girl'."

But even now, being included can clash with being black. Asked how it felt to be called "racist" that night at Ivy, Kennedy stammers as she struggles not to offend either the students stuck outside the club or the ones huddled inside—then quickly seeks refuge in stats. "My year, we have seven [black members]," she says. "Seven is actually 10 percent of my class … so if 10 percent of the country's population is black, then OK, there you go." Ultimately, Kennedy believes the eating clubs are exclusive, not discriminatory: "a little intimidating" for black students, sure, but "also just intimidating for everyone." When pressed, however, she admits to grappling with occasional pangs of guilt. "There's still some stigma and some obstacles," she says. "I was particularly lucky. I don't think maybe all my black colleagues would have felt the same way." Having to please everyone as she defines herself in two worlds is a heavy load to shoulder, and most of the time Kennedy acts as if it isn't there. But it always is.

Half black, half Puerto Rican, Kamille Davis entered Princeton with the same advantages as Alex Kennedy—Princeton legacy, "mostly white" schools, no real racial barriers to overcome. But unlike Kennedy, she soon drifted away from the white mainstream. "Princeton was the first chance [Kamille] ever had to be around a lot of highly intelligent, broad-interest black kids," says her father, Jerome. "She definitely seized it." An active member of the Black Student Union, Davis spent much of her time volunteering at a local middle school, talking to kids about race, class and violence; she even joined an effort to establish an all-black eating club. As a result, she left Princeton with a social circle much smaller, and much blacker, than her father's, and even now, no one in her self-described "core group of seven [Princeton] friends" is white. Asked to explain why "it looked like all of her friends were black," as her dismayed dad recently put it, Davis emphasizes that Princeton has changed since the time when African-Americans "really had to bond together or [they] would be completely isolated." She's quick to characterize the BSU as "just another group of friends."

Still, there's a reason that Davis felt more connected to her black classmates than their white counterparts: at post-racial, meritocratic Princeton, it's often impossible to say where color ends and exclusivity begins. Like any other a cappella leader, she was upset when her group, Culturally Yours, was rejected from the "arch rotation"—a lineup of eight premier outfits selected to sing together under the school's ancient Gothic portals. Her girls had worked for weeks to perfect their harmonies. But unlike her fellow runners-up, Davis was forced to confront something deeper than disappointment—namely, the suspicion that "maybe it was race-motivated." After all, Davis thought, Culturally Yours is the only all-black, all-female group on campus. After struggling to decide whether to stay silent or risk backlash by protesting, she eventually sent the other a cappella presidents a message detailing the ways "we'd been kind of discriminated against." She received some sympathetic responses—but nothing changed. "It was such a stressful, almost kind of infuriating thing," she admits. It wasn't the last time Davis would feel out of place. In a seminar on discrimination and the law a year later, a white student suggested that Princeton settle the reparations dispute by forcing his fellow Caucasians to serve black classmates as "slaves for a day." Shocked, Davis spoke up, but her peers mistook her protest for hypersensitivity and kept laughing. In both cases, Davis quickly backed down. Even today, she says she feels guilty for complaining.

The problem is, she might've felt the same guilt if she hadn't. In a post-racial bubble, it's no longer the initial incident that makes being black uncomfortable; when everyone has "gotten over" race, any controversy can be easily explained away as a joke, or a misunderstanding, or ordinary, colorblind Ivy League exclusivity. But while Henry Kennedy and Jerome Davis had an outlet for their concerns, Alex and Kamille don't. Even worse, they have the uncomfortable burden of deciding whether they should even be concerned to begin with. As a result, they, like many young, elite African-Americans, can feel boxed in. When injustices do arise, there's pressure to brush them aside. To do otherwise would be to think too clearly in racial terms—to clash too openly with post-racial expectations. Ignoring them entirely, though, might look like a retreat from community obligations. Everyone's a loser and everyone shares the guilt.

There is, of course, no one "black experience." And Princeton hardly represents America at large. But despite its past, the institution and others like it have recently become surprising models for how post-racialism, if it ever arrives, will take shape.

It's clear from the collegiate careers of Alex Kennedy and Kamille Davis that the transition won't be trouble-free. But what's also clear is that this friction may have more to do with us than them. Lucky enough to have grown up as "princesses" in places where race was irrelevant, Kennedy and Davis have the luxury of no longer fighting their father's battles—or living in black and white. But while they see themselves as "students first," the rest of us are still catching up. Even now, we're tempted to typecast these women in stereotypical molds: Davis is defending her roots; Kennedy is retreating into an Ivy fortress. The opposite also has its appeal: Kennedy might seem more progressive; Davis, confined to her comfort zone. Ultimately, it's these conflicting expectations—and not an internal identity crisis—that make the post-racial life so disorienting for members of the new black elite.

Alex Kennedy hasn't tried to hand out passes since that spring evening at Ivy. Now a senior, she'll give them to anyone who asks, but standing outside every night would be impractical. More than that, it would be strange. There's no reason to spend her days helping black students she doesn't know. "In a sense it's privilege," she says. "But it's also just my life." As Kennedy sees it, she's simply asking to be judged for who, not what, she is. Will institutions like Princeton show us how to make that happen? Kennedy sighs. "I don't think," she says, "that we can move too much faster than the world."