20 celebrity couples with whom millennials are oddly obsessed (2024)

From MTV’s TRL to TMZ, millennials were (unfortunately) raised at the start, and really the pinnacle, of celebrity worship. Taught in their youth to scream incoherently at the sight of a famous face, they are the generation that could deliver the oral history of the infamous jean ensembles worn by Britney and Justin just as easily as they could break down why a character by the name of Seth Cohen is forever on a pedestal for male perfection.

Millennials love the rich and famous, but even more so, they love it when those celebrities hook up. Over the years, there have been a number of celebrity couples to which millennials have attached themselves. Whether or not said pairs lasted doesn’t matter because these are the celebrity couples millennials are obsessed with.

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For younger people who might be reading this, Sarah Michelle Gellar and Freddie Prinze Jr. are the millennial versions of Zendaya and Tom Holland. They are a costars-turned-couple that your generation would be absolutely devastated with if they parted ways.

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At first, Britney and Justin seemed like a perfect pairing. They were the Tiger Beat royalty when millennials were kids. The pop princess dating one of the biggest names to ever synchronize dance in a boy band? Talk about amazing! Then, of course, came the drama of “Cry Me a River” and, years later, the trauma of Britney’s memoir. However, there will always be something enticing about those two. Perhaps that timeless image of them in all denim.

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"Bennifer" was a moment, and in hindsight, it’s hard to really know why. Maybe because Jennifer Lopez’s marriages are, by themselves, a tabloid addiction? Whatever the case, millennials were there for the start of it all in her “Love Don’t Cost a Thing” video and the box office nightmare that was Gigli, but also there when Ben and Jen decided to try again in 2021.

Disney Channel

Hilary Duff was a Disney Channel icon by the time she and Lindsay Lohan allegedly fought for the love and attention of the late Aaron Carter, and millennials were heavily into every detail, but in the end, many sided with Duff on the matter.

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Was "Brangelina" the first instance of a celebrity couple's name? Maybe so, but when two of the biggest names in Hollywood connect, it’s going to be something people latch onto. Of course, things weren’t so fairy tale for this pair, with many taking Angelina Jolie’s side in the end.

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MTV was handing out reality shows left and right in the early ‘00s, and if the network couldn’t land one with Britney and Justin, they were going to have to settle on another pop singer and boy band member. However, thanks to Jessica Simpson’s soundbites, the show went viral before going viral was even a thing.

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Tommy Lee and Pamela Anderson do lean more toward Gen X, but they were the initial lesson in the birds and the bees for many young, impressionable millennials years before Kim and Ray J.

The WB Television Network

The O.C.was an instant favorite for millennials in their teen years. It was Beverly Hills, 90210, complete with Ben McKenzie looking over 30 but somehow being in high school. His questionable age aside, The O.C. featured the love story of the beautiful, popular girl and her nerdy neighbor who’d fawned over her for years. When Summer and Seth finally got together on the show, fans rejoiced. However, they weren’t just together on screen, but off. Today, each has moved on, but there’s something in every O.C.fan that hopes for them to reconnect one day, if not for anything, at least a Summer/Seth ad spot.

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Carson Daly was the face of MTV, and Tara Reid was an American Pie favorite. Were they the Romeo and Juliet of the ‘00s? Absolutely not, but they were a weird pair that millennials look back on and go, huh, remember that?!

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To some, the golden age of reality TV was the years in which VH1 rolled out a cascade of dating shows, all of which started with Flavor of Love. On said show, former hype man and current US women’s water polo team sponsor Flava Flav had his own version of The Bachelor, and on that initial season (there were others and spinoffs), Flav met Tiffany “New York” Pollard. Was it true love? Who’s to say, but what millennials loved most was that they made magical reality television together.

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This couple was like those car crash instances in which no one can really ever look away.

New Line Cinema

The Notebookgave this generation so much more than an appreciation for writing letters every day for a year, but also the real-life couple that consisted of its stars: Ryan Gosling and Rachel McAdams. While their relationship was short-lived to many, millennials will hold onto two things: the movie, of course, and the moment from the MTV Movie Awardsin which they won "Best Kiss" and recreated the scene onstage.

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Mariah Carey provided the soundtrack to their childhoods, while Nick Cannon was someone they knew from Nickelodeon and movies like Drumline. So when the two not only got together but then had kids, it was odd at first, but ultimately, millennials stayed in tune with the pair over the years despite them not staying together and Cannon going on to have way more children.

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The number of millennials who were sexually awakened by the happenings of Cruel Intentions is a lot, and because of that, millennials are forever grateful for the movie and real-life couple that was Reese Witherspoon and Ryan Phillippe.

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A huge movie star marrying one of the biggest TV stars? It was a match made in celebrity obsession.

Columbia Pictures

Did Justin Diaz and Justin Timberlake make much sense? Not at all, but that’s par the course for Diaz, who’d later marry Good Charlotte’s Benji Madden — another couple that had millennials scratching their heads while simultaneously watching their every move.

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If millennials were to make a mixtape of the songs that owned their CD player in the 2000s, Ashanti and Nelly would have several tracks across the board. So, dating for a decade back in the day and rekindling things warms hearts.

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When they talk about people who could match one another’s freak, they’re referring to Angelina Jolie and Billy Bob Thronton.

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Hilary Duff and Joel Madden had quite the age gap, which made many millennials look at this pair with a side-eye. This is still something they will talk about when reminiscing about the stranger celebrity couples they grew up with.

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Alanis Morissette allegedly wrote her hit “You Oughta Know” about Full House’s Dave Coulier, a.k. Joey, a.k.a. the guy with the woodchuck puppet. This is something millennials heard through a literal grapevine as kids because the internet then was not the rapid-fire information highway it is today. So, this interest spawns more from the urban legend of it all than the reality it could be based on.