Hailey and Justin Bieber, Nicola Peltz and Brooklyn Beckham, Cole Sprouse and Lili Reinhart (while they lasted). It is an undeniable fact that celebrity couples can shape the zeitgeist – or an era if you’re Kim Kardashian and Kanye West. But today we’re looking back to the couples we forgot were a thing in the 90s and early 00s.

Penelope Cruz and Tom Cruise

Penelope Cruz Tom Cruise
Actor Tom Cruise and actress Penelope Cruz attends the ‘Captain Corelli’s Mandolin’ Beverly Hills Premiere on August 13, 2001 at Academy of Motion Picture Arts and Sciences in Beverly Hills, California. (Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images)

When Cruz met Cruise. It was the year 2000 when Tom Cruise and Penelope Cruz were both cast in the film Vanilla Sky. At the time of shooting, Cruise was still married to Nicole Kidman.  A year later, Kidman and Cruise had split and the latter made his relationship debut with Cruz at the premiere of Captain Corelli’s Mandolin. They broke up three years later. Cruz spoke some universal truths to The Telegraph at the time. “I’ve never fallen in love with someone I’m working with. It’s always been afterwards. If something becomes friendship, then maybe months later it becomes something else, but you can never know, it’s always a mystery. You can’t plan those things.”

Mila Kunis and Macaulay Culkin

Mila Kunis and Macaulay Culkin
Macaulay Culkin and girlfriend Mila Kunis during Ubid.com Joins Forces with Hollywood Stars to Launch Celebrity Auction to Benefit Hurricane Victims – Inside at Empire Ballroom in Las Vegas, Nevada, United States. (Photo by Chris Polk/FilmMagic)

If you can’t imagine Kunis with anyone other than Ashton Kutcher, then think again. The Black Swan actress dated Home Alone star Macaulay Culkin for eight years. They first got together in 2002. In a 2009 interview with Women’s Health (via Cheat Sheet), Kunis said of their relationship, “You find a steady rock in your life, and that’s all you need. We have our ups and downs, but work through them”. As we know, Kunis later went on to reconnect with her That 70s Show on-screen beau Kutcher. And the rest is history.

Matthew Perry and Julia Roberts

Matthew Perry and Julia Roberts
304422 21: Actor Matthew Perry and actress Julia Roberts hug each other on the set of “Friends.” (Photo by Liaison)

A Friends and Pretty Woman crossover event? Never happened. Or did it? The Hollywood Reporter said that Julia Roberts’ single episode appearance involved “plenty of flirting via fax machine” by Matthew Perry, better known as his character, Chandler. Nothing has ever sounded so 90s. Apparently, rom-com queen Roberts told Perry she would appear on an episode of Friends if he wrote her an essay on Quantum Physics. And he did. Overnight. The actor is also said to have sent Roberts a ‘why you should date me’ questionnaire, with the writers of the show helping him out. The pair dated in 1996 and went their separate ways shortly after that. How did we miss this one?

Alanis Morissette and Ryan Reynolds

Alanis Morissette and Ryan Reynolds
Alanis Morissette and Ryan Reynolds during “Blade: Trinity” Los Angeles Premiere – Red Carpet at Grauman’s Chinese Theater in Hollywood, California, United States. (Photo by Jon Kopaloff/FilmMagic)

Yet another couple we must have blinked and missed. Introduced to each other at Drew Barrymore’s 2002 birthday bash, iconic musician Alanis Morissette and then-little-known actor Ryan Reynolds were engaged in 2004 for a total of three years before they split. Morissette’s 2008 solo album was written about her breakup with Reyonolds, with her song “Torch” specifically written about her grief.

Tom Cruise and Cher

Tom Cruise and Cher
Tom Cruise & Cher backstage. (Photo by MCaulfield/WireImage)

Next up in couples that we question in the 2020s: Tom Cruise and Cher. How and why, I hear you ask? In fact, we may not even have known about this romance at the time. The 70s style icon revealed on Watch What Happens Live with Andy Cohen that she dated Cruise at the beginning of his career. “He was in the top five [of boyfriends]. It’s not a long list, just a good list.” She goes on to say, “It could have been a great big romance because I was crazy for him.”

Janet Jackson and Matthew McConaughey

Janet Jackson and Matthew McConaughey
Janet Jackson and Matthew McConaughey at the 44th Annual Grammy Awards at the Staples Center in Los Angeles, CA. 2/27/2002 Photo by Frank Micelotta/ImageDirect

This couple first met at the Grammy Awards in 2002. It was never officially confirmed at the time with McConaughey admitting only in 2019 that he and Jackson had briefly dated. “We went and had dinner one night. That was sorta it,” he told Watch What Happens Live.

Ashton Kutcher and January Jones

Ashton Kutcher and January Jones
Ashton Kutcher and January Jones (Photo by Jim Smeal/Ron Galella Collection via Getty Images)

In 2009 towards the beginning of the Mad Men series and January Jones’ rise to fame, the actress told GQ that Ashton Kutcher was her first boyfriend. In the interview, she insinuated that it was Kutcher’s lack of support that caused them to break up.

“[He] was not supportive of my acting. He was like, ‘I don’t think you’re going to be good at this’. So, f**k you! He only has nice things to say now.” Jones went on to extend what could be interpreted as an olive branch (kind of). “If anything, I should thank him, because the minute you tell me I can’t do something, that’s when I’m most motivated.” And we are grateful for whatever butterfly effect that set off, to have January as our Betty Draper.

Josh Hutcherson and Vanessa Hudgens

Josh Hutcherson and Vanessa Hudgens
MELBOURNE, AUSTRALIA – JANUARY 15: Actors Vanessa Hudgens (L) and Josh Hutcherson arrive for the world premiere of “Journey 2: The Mysterious Island” at Village Cinemas Jam Factory on January 15, 2012 in Melbourne, Australia. (Photo by Graham Denholm/Getty Images)

Josh Hutcherson was hot property following the successful of The Hunger Games franchise. Vanessa Hudgens can attest to that. After splitting with Zac Efron whom she met on the set of High School Musical, Hudgens dated Hutcherson briefly before they went their separate ways. But not before they completed the press rounds for the film they both starred in, Journey 2: The Mysterious Island, however. On the Australian morning show, TODAY, the two were asked how long they’d been dating. There was a brief moment of awkwardness before Josh clarified, “We were at one point, but she broke my heart,” he laughed. “I’m just kidding. That was a while ago, we’re just really good friends now.”

Natalie Portman and Jake Gyllenahaal

NEW YORK – NOVEMBER 18: Actor Jake Gyllenhaal and FINCA Ambassador of Hope, actress Natalie Portman attend the FINCA 25th Anniversary gala event at Capitale Bowery on November 18, 2010 in New York City. (Photo by Neilson Barnard/Getty Images for FINCA)

Talk about a power couple! In 2006, Natalie Portman and Jake Gyllenahaal shared in a brief tryst before breaking it off as reported by Mamamia. In 2011, Gyllenhaal poked fun at Portman as he presented her with the Desert Palm Achievement Award. “She’s a vegan, which makes it really frustrating when you’re picking a place to eat.” In 2021, I somehow feel like this would be a much easier task, especially in Los Angeles. The two are said to be good friends to this day.

thoughts?