The Way They Were…
EMILIE: Valentine’s Day has come and gone, and with it, we took some time this week to remember the it couples of the late ‘90s/early ‘00s.
It was a wild ride.
There were so many iconic couples. Some we thought would last forever (Brad and Jen!), some who actually did (Sarah Michelle Gellar and Freddie Prinze Jr.), and others that were never meant to last (Cameron Diaz and Jared Leto). Then there were some that came out of absolutely nowhere (Tom Cruise and Katie Holmes, who were engaged after less than three months of dating).
We also revisited a few costar couplings (Ryan Gosling and Rachel McAdams), some fun paparazzi eye candy (Jake Gyllenhaal and Kirsten Dunst), an on/off Miramax (ugh) star couple (Ben Affleck and Gwyneth Paltrow), and a weird couple that didn’t really seem to have anything in common other than being Canadian (Alanis Morrissette and Ryan Reynolds).
We have to start with the obvious, because people are still talking about whether they’ll get back together after a friendly SAG Awards reunion.
She: one of the stars of Friends who dated Tate Donovan from 1995-1998. Before dating Donovan she also dated Adam Duritz from Counting Crows. who would later date her Friends co-star Courteney Cox at one point. Yeah, apparently a white dude with dreads can get around in Hollywood.
He: a movie actor who dated several co-stars in the early ‘90s, including Robin Givens, Jill Schoelen, and Juliette Lewis. Later, he dated his Seven costar Gwyneth Paltrow from 1994–1997, and even get engaged.
Brad and Jen met in 1994, but went on their first date in 1998 after being set up by their managers who were friends. They made their red carpet debut at the 1999 Emmy Awards, and he proposed to her later that year.
Brad and Jen were EVERYWHERE. They were beautiful, yet approachable. They had a 200-person Malibu wedding in 2000 with a gospel choir and fireworks, but they had written their own vows. They could totally be your hot couple friends.
In the end, it was not meant to be. Brad met his Mr. and Mrs. Smith costar Angelina Jolie in 2003 when they start filming. Rumors start to circulate of their on-set chemistry. Pitt and Aniston would announce their split on January 7, 2005, a week after having vacationed with Courteney Cox then-Arquette, and her then-husband David Arquette.
Over the years, a lot has been made of this relationship and Brad and Angelina were first seen as a controversial couple because people believed them to have had an affair. Ultimately, though, in hindsight, Pitt and Aniston ended things fairly amicably.
Fifteen years a marriage each later, people have never stopped hoping the two of them would get back together one day. Guys, get over it. Exes can be amicable without them getting back together. The end.
As we mentioned earlier, Brad Pitt dated and was engaged to Gwyneth Paltrow in the mid-to-late ’90s. Post-split, Gwyneth would go on to date Ben Affleck.
Gwyneth Paltrow and Ben Affleck had an on-and-off three-year relationship from 1997-2000. They met at dinner hosted by Harvey Weinstein (already a bad omen); Gwyneth was fresh out of her relationship Brad Pitt (they were engaged, and she would go on to say she mourned her relationship with Pitt for five years, making Affleck a full-blown rebound).
They would act in Shakespeare in Love together, but broke up in ’99, hence her awkward shout out to him in her acceptance speech. They got back together — at least publicly — not too long after Gwyneth tricked Ben into starring in Bounce. She got him to play a businessman who gives up his seat to a man on a flight that later crashes, then swoops in and grief-bangs the widow.
Like most breakups, even among normies, it was a culmination effect that lead to their demise. First of all, the beloved (now Oscar winner) Brad Pitt is a tough act to follow. Especially if you’re Blythe Danner and RIP Bruce Paltrow, who loooooved Pitt and were sorta ‘meh’ on Affleck, who, as Paltrow would later describe him as “not in a place to have a girlfriend.”
Paltrow also had a bit of open disdain for Affleck’s movie choices. She told NYT in an article about Affleck in promotion of Bounce, called his roles in Armageddon, Forces of Nature, Pearl Harbor, and Saving Private Ryan as movies that didn’t “push him”.
Ultimately, they break up in 2000. During this time, Winona Ryder was Gwyneth’s best friend. She introduced Ryder to Matt Damon and they all spent a lot of time out on double dates together.
They had some massive falling out around the time Paltrow and Affleck were splitting up, because Gwyneth stole the lead role in Shakespeare in Love from Winona. ALLEGEDLY. Apparently she saw the script at Ryder’s house, asked if she could read it, auditioned for the role, got it, and won an Oscar.
This comes back up on Goop in 2009, when the VERY FIRST article on this cursed website posts drags Winona:
“Back in the day, I had a ‘frenemy’ who, as it turned out, was pretty hellbent on taking me down.” She went on to write: “I restrained myself from fighting back. I tried to take the high road. But one day I heard that something unfortunate and humiliating had happened to this person. And my reaction was deep relief and happiness.” Wow. #FreeWinona
Though these couples were high-profile, there was nothing particularly weird about their pairings, unlike this next couple:
Katie Holmes had dated actor Chris Klein from 2000-March 2005 (they even got engaged in 2003). Tom Cruise had been married twice, first to actress Mimi Rogers from 1987–1990, who introduced him to Scientology, and later to his Days of Thunder costar Nicole Kidman, from 1990–2001. In a 2004 interview with Seventeen, Holmes talked about her crush on Tom Cruise and how she had a poster of him growing up and thought she was going to marry him.
The following is the most bonkers timeline EVER:
One month after Holmes broke off her engagement with Chris Klein, she and Cruise are seen publicly for the first time (April 2005). The next month Cruise goes on Oprah to declare his love for Holmes and infamously leaps on top of the sofa. A month later, Holmes says she’s going to convert to Scientology and the couple announces their engagement. In October of that year, the couple shares they’re having a baby and Holmes would go on to give birth to Suri Cruise in April of the following year. A few months later, the family graced the cover of the October 2006 issue of Vanity Fair, and they would get married in Italy the following month (Head of the Church David Miscavage was the best man, #WheresShelly).
During this time, Cruise was known for being a devout Scientologist, but we began to get a closer look into just how far up he is in the Church when an indoctrination video, strictly meant to be for members of the church, went viral in 2008.
Over the next few years, the couple isn’t as much in the limelight, but they still gush about each other in interviews. The first signs of the end came when Cruise appeared at the Rock of Ages movie premiere without Holmes in June of 2012, and later that month, the couple announced their split, which was allegedly due to her opposition to the Church of Scientology and raising Suri as a Scientologist. Their divorce settlement gave Holmes sole custody of Suri, while Cruise had visitation rights. One of the alleged conditions was that she couldn’t “embarrass” Cruise for five years after their divorce, which meant no high-profile relationships, hence her relationship with Jamie Foxx was never talked about.
The next relationship was another strange pairing. Because we do not care for Jared Leto one bit, we’re centering this whole relationship on only part of this relationship wecare about: CAMERON FUCKING DIAZ.
If you’re keeping score at home, in the Cameron Diaz has pulled SOME DUDES where we are at this point in her dating timeline: post Matt Dillion, pre-Justin Timberlake.
Because Diaz was pretty private even back in 1999, it’s hard to tell when/how they met, but they officially got together in August 1999, got engaged in 2002, and split in March 2003, according to some because Cameron Diaz’s career was really taking off. Leto was in his Thirty Seconds to Mars phase.
Here are some of the movies Diaz made was in while she dated Leto:
- Any Given Sunday
- Charlie’s Angels (the good one)
- Gangs of New York
- The Sweetest Thing
We’ve gone from an LA couple if ever there was one to an adorable Canadian pairing. He, a boy from Vancouver, she, a girl from Ottawa
Alanis Morrisette had very famously dated Dave Couiller, aka Uncle Joey from Full House, in the early ‘90s. This breakup inspired Jagged Little Pill, which still slaps as an album. The song “You Oughta Know” is allegedly about him, which she’s never confirmed, but if true, implies that she did, in fact, go down on Dave Coulier in a theater.
Meanwhile, Ryan Reynolds had previously dated Melissa Joan Hart, as well as Kristen Johnson, and Rachael Leigh Cook. Morrisette and Reynolds met in 2002, while attending Drew Barrymore’s party, which is equally as 2002 as Cameron Diaz and Jared Leto, and started dating pretty shortly after that. They announced their engagement in 2004 and broke off the engagement in 2007.
After dating/marrying/divorcing Scarlett Johansson, Reynolds dated his Green Lantern costar Blake Lively, and got married at a plantation (bet they don’t regret that AT ALL). They have three daughters together and seem pretty happy. As for Alanis, she married a rapper named Souleye in 2010 and has three kids.
We have another Canadian couple on this list, Ryan Gosling and Rachel McAdams.
They met on the set of The Notebook in 2003 and notoriously fucking hated each other. There’s a story director Nick Cassavetes tells about how Gosling pulled him aside one day and asked for the script supe to read McAdams’ lines off camera to him so he didn’t have to physically share the scene with her. So Cassavetes’ solution was to let them yell it out in a room with a producer.
Apparently that helped and they were able to convey some modicum of chemistry enough to build a wild fan base who were way too invested in them on and off screen (as we’ve discussed in our Nicholas Sparks episode, this book/movie is hella problematic).
Gosling said the switch from love to hate happened a few years later when they ran into each other in New York. And then, how could we forget their infamous couple coming out party at the 2005 MTV Movie Awards? They shocked everyone by reenacting their jump-kiss in the rain, but like, for really real.
They broke up initially in 2007, but got back together briefly in 2008, only to break up again for good, citing the standard “busy schedules.” They both are now married to other people and have kids.
Another cute couple from the early-to-mid 2000s was Jake Gyllenhaal and Kirsten Dunst, everyone’s favorite “oh, look, they’re they are walking their dog like normal people” couple.
They got together in 2002 when they were introduced to one another by Jake’s sister Maggie, who had worked with Dunst had on Mona Lisa Smile. They dated from 2002–2004, and during that time they bought a house together in LA and adopted a German Shepherd mix puppy. They also were often seen out and about walking said dog, running errands, and eating out.
Dunst dated Garrett Hedlund from 2012–2016, who she met on the set of On the Road. She would later start dating Jesse Plemons in 2016, who she met while filming the show Fargo. They would later get engaged and have a kid together in 2018.
Jake Gyllenhaal briefly dated Natalie Portman and then dated Reese Witherspoon from 2007–2009 (right after she had split from Ryan Philippe) and then dated Taylor Swift from 2010–2011 (the maple latte dates that would turn into song inspo for the album Red), as well as model Alyssa Miller from 2011–13 and is currently dating model Jeanne Cadieu. Please don’t pull a Leo, Jake.
Thankfully, one of our couples has stood the test of time, and are still very much together, like our generation’s Rita Wilson and Tom Hanks. Our king and queen Freddie Prinze Jr. and Sarah Michelle Gellar.
They recently celebrated 20 years together (17 married). Even though the met in 1997 on the set of I Know What You Did Last Summer, they didn’t start dating until 2000 when what was supposed to be a casual friend date turned into a romantic date. They credit being friends for a few years before getting together as a key to their successful relationship.
They were engaged in April 2001, and per popbitch: Prinze celebrated his engagement to Gellar by buying his n hers bowling balls.
They married in Mexico in September 2002, but not without some natural disasters along the way. First, Hurricane Hernan came through, forcing their outdoor wedding indoors, and then, at the end of the night, when everyone was getting back to their hotel, 4.6 earthquake hit.
But other than that, their wedding was fairly small (60 people), with Gellar’s mom walking her down the aisle and Adam Shankman officiating their ceremony.
They’ve gone on to not only live happily ever after, but also play love interests in two Scooby-Doo movies and frequently voice characters on Star Wars Rebels, and other features.
In 2007, for their fifth anniversary, Gellar changed to her last name to Prinze and surprised FPJ by showing him her drivers license with her name changed to Sarah Prinze. They also recently did the cutest Cascade sponcon, which we stan:
All in all, it was a strange but fun walk down celeb couple memory lane. We all hope you spent your Valentine’s Day with someone special who at least looks at you with less disgust than Jake Gyllenhaal watching Kirsten Dunst eat salad.
