20 celebrity couples with whom millennials are oddly obsessed

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.

Despite both being born right at the cut-off to be millennials, Zendaya and Tom Holland definitely lean more toward Gen Z. However, all it took was one lip sync battle where Spiderman himself was dressed as Rihanna for an entire generation to become utterly obsessed with every move this marvelous couple makes.

"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.

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.

After millennials finally got over the fact that John Krasinski wasn’t going to marry his Office costar, Jenna Fisher, they accepted and loved him with Emily Blunt just the same.

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.

She’s a Spice Girl and he’s a handsome athlete. It just makes sense to obsess.

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.

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?!

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.

Gen X has Garth Brooks and Trisha Yearwood. Millennials have Tim McGraw and Faith Hill mostly because McGraw did that one song with Nelly (part hilarious, part iconic), and Faith somehow made the phrase “centrifugal motion” work in a song.

The Notebook gave 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 Awards in which they won "Best Kiss" and recreated the scene onstage.

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.

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.

The interest in this couple is all due to millennials’ insane interest in being extreme in the ‘00s from Pink’s extreme look when she debuted to Carey Hart’s extreme motocross ways.

A huge movie star marrying one of the biggest TV stars? Yes, please!

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.

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

For a lot of millennials, Barack Obama was the first president they cast their vote for in an election. That reason alone keeps him close to the hearts of many, but no one can deny that when it comes to really cool couples who’ve occupied the White House, the Obamas are at the top of the list between his tan suit and her toned arms.

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.