14 Totally '90s Couples You Haven't Thought About in 30 Years
14 Totally '90s Couples You Haven't Thought About in 30 Years
Alexandra Schonfeld, Carson BlackwelderSun, April 5, 2026 at 12:30 PM UTC
0
Toni Braxton and Shemar Moore. ; Matthew McConaughey and Sandra Bullock.Credit: Ron Galella/Ron Galella Collection via Getty -
Not all celebrity couples stand the test of time — but that doesn't mean their romance didn't burn bright when they were together
Paula Abdul and John Stamos, Sandra Bullock and Matthew McConaughey and Drew Barrymore and Luke Wilson are just some of the "It" couples from the '90s
Many of these nostalgic Hollywood pairs met and started dating while playing love interests on-screen, including Keri Russell and Scott Speedman
As celebrities join in on the "What were you like in the '90s?" trend in 2026, it's time to revisit forgotten Hollywood couples who dated during the decade.
Though it's been more than 30 years since these stars held hands on a red carpet or cuddled up on a vintage couch, we dug through the archives and pulled out our favorite photos of totally nostalgic pairings.
From Toni Braxton and Shemar Moore's sexy award show looks to Sandra Bullock and Matthew McConaughey's memorable appearances, the following duos will have you reminiscing on their style, star power and sweet love stories — despite their romance coming to an end.
Here's a look back at former "It" couples you might not have thought about this millennium.
01 of 14
Matt Dillon and Cameron Diaz
Matt Dillon and Cameron Diaz attend the Valentino fashion show together in Paris in October 1997Credit: Pool PAT/ARNAL/Gamma-Rapho via Getty
After meeting years before on nearby film sets, actors Matt Dillon and Cameron Diaz dated in the 1990s and costarred in the 1998 rom-com There's Something About Mary.
Diaz told The Guardian in 1997 (via The Sun), "I love him incredibly."
Years after their relationship ended, Dillon told Parade, per CBS News, that Diaz was a "muse."
"It's a very powerful thing when you feel that way about somebody," Dillon said of falling in love. "Cameron was a muse for me. I hadn't been in any deep emotional relationships."
Diaz now shares two children with husband Benji Madden, whom she has been married to since January 2015. Dillon dated Italian actress Roberta Mastromichele for years, but the two have since split up.
02 of 14
Paula Abdul and John Stamos
Paula Abdul and John Stamos are seen with their arms around each other in 1990Credit: Vinnie Zuffante/Getty
John Stamos and Paula Abdul dated for a time and have maintained a friendship over the years.
In May 2015, Stamos shared an old photo of them on Instagram, captioning it, "Cold Hearted Snake and America's sweetheart. Together again and it feels so good."
Later that year, Abdul shared a throwback snap on Instagram of her standing between the Full House alum and Frank Sinatra as she smiled for the camera.
Stamos and Caitlin McHugh Stamos wed in an intimate ceremony in February 2018 and welcomed their son, Billy, that same year.
03 of 14
Scott Wolf and Alyssa Milano
Scott Wolf and Alyssa Milano attend a Hole concert in 1999Credit: Jeff Kravitz/FilmMagic
Scott Wolf and Alyssa Milano dated briefly in the early '90s after meeting on the set of Double Dragon in 1993.
They were even engaged for six months before the relationship ended amicably in 1994.
"I knew it the second I met him," Milano told PEOPLE during their whirlwind romance. "I called my mom and told her, 'This is the man I'm gonna marry.' "
Wolf agreed: "I could have asked her to marry me two weeks after we met. I'm convinced we're like two halves of the same soul."
The Charmed alum shares two children with husband David Bugliari, while the Doc star shares three children with estranged wife Kelley Wolf.
04 of 14
Sandra Bullock and Matthew McConaughey
Sandra Bullock and Matthew McConaughey attend the 'In Love and War' premiere at DGA Theatre in L.A. on Jan. 20, 1997Credit: Ron Galella, Ltd./Ron Galella Collection via Getty
Long before they both became Oscar winners, McConaughey and Bullock dated after meeting on the set of the 1996 film A Time To Kill.
"We dated for a while after A Time to Kill, and we're still friends," McConaughey told Playboy in December 2016. "She and I have another version of our relationship to put on film, and we're looking for something. She's not a little girl. She's a woman. She could run a country."
McConaughey now shares three kids with wife Camila Alves McConaughey, whom he married in his native Texas in June 2012.
Bullock is the proud mom of two children, both of whom she welcomed through adoption. The Lost City actress dated photographer Bryan Randall from January 2015 until his death in August 2023.
05 of 14
Toni Braxton and Shemar Moore
Toni Braxton and Shemar Moore at the 9th Soul Train Music Awards in March 1995Credit: Ron Galella/Ron Galella Collection via Getty
Moore was one-half of a few iconic '90s couples — including this memorable pairing with Braxton in 1995.
While telling PEOPLE in November 2024 about his "pretty good entrance into Hollywood," he explained how he became known as "the guy who dated Halle Berry [in 1997] and Toni Braxton [in 1995]."
These days, Moore is dad to daughter Frankie, whom he welcomed in January 2023 with ex-girlfriend Jesiree Dizon. Braxton shares two children with ex-husband Keri Lewis.
The "Un-Break My Heart" singer later married rapper and Cash Money Records co-founder Birdman in August 2024.
06 of 14
Scott Speedman and Keri Russell
Scott Speedman and Keri Russell attend the WB Summer TCA Press Tour All-Star Party in Pasadena, Calif., on July 25, 1998Credit: Jim Smeal/Ron Galella Collection via Getty
While Scott Speedman and Keri Russell played love interests on-screen as Felicity and Ben on Felicity from 1998 to 2002, they also dated in real life for a time.
While they both are now in long-term relationships with other people, the two have remained good friends.
Russell is a mom of three and has been dating her longtime partner, The Americans costar Matthew Rhys, since 2013.
Advertisement
Speedman shares two children with fiancée Lindsay Rae Hofmann.
07 of 14
Edward Furlong and Natasha Lyonne
Edward Furlong and Natasha Lyonne attend the 'American Pie' premiere in 1999Credit: Barry King/Liaison
American Pie is about as '90s as it gets, and Terminator 2: Judgment Day star Edward Furlong and Natasha Lyonne attended the 1999 premiere of the movie together.
In a May 2014 interview with Harper's Bazaar, the Poker Face actress revealed she and Furlong "were together for a while" and she "was crazy for him on the [Detroit Rock City] movie set" as costars.
08 of 14
Andrew Keegan and LeAnn Rimes
Andrew Keegan and LeAnn Rimes attend the 'Broken Hearts Club' premiere at the Egyptian Theatre in L.A. on July 17, 2000Credit: Ron Galella/Ron Galella Collection via Getty
LeAnn Rimes and Andrew Keegan met as teenagers, initially connecting after the Grammy-winning singer spotted him in a magazine.
"I started dating Andrew Keegan at 15," she told The Sydney Morning Herald in October 2022. "He was an actor in teen movies, and we were together for three years. While filming a video clip for my song 'Commitment in Santa Monica,' I flicked through a Teen Beat magazine and spotted him."
She continued, "I told my manager and hair and make-up artist that I thought he was cute. Next minute, my then manager called Andrew and asked if he wanted to meet me; that's how we hooked up."
Keegan now shares daughter Aiya Rose with Arista Ilona, while Rimes is married to Eddie Cibrian and is stepmother to his two sons, whom he shares with ex-wife Brandi Glanville.
09 of 14
Jewel and Sean Penn
Jewel and Sean Penn attend an event at the Mann National Theatre in L.A. on Nov. 9, 1995Credit: Jan Jarecki/Penske Media via Getty
Jewel and Sean Penn had a brief romance after meeting in 1995, which she discussed in her book Never Broken: Songs Are Only Half the Story.
Following her performance on Late Night with Conan O'Brien, Penn reached out to Jewel over the phone — a move her Alaska-based father first wrote off as a prank call.
"One day, my dad came to find me, saying, 'Jewel, you must be getting some kooky fans out there in the Lower 48. Some guy just prank-called and said he was Sean Penn,' " the "Who Will Save Your Soul" singer wrote.
After asking her to compose a song for a movie he was working on, the two met, and Jewel wrote that she found him "charming, witty, and bright."
Penn now shares two children with ex-wife Robin Wright; Jewel shares son Kase with ex-husband Ty Murray.
10 of 14
Kathy Griffin and Jack Black
Kathy Griffin and Jack Black in a throwback photo Griffin shared on TikTok on Feb. 26, 2025Credit: Kathy Griffin/TikTok
Kathy Griffin and Jack Black were together in the 1990s — though, in a TikTok post in February 2025, Griffin revealed: "Dating is a very loose term."
"This is a picture of me and my then-boyfriend, Jack Black, who you probably know mostly from School of Rock," Griffin wrote alongside the throwback shot. "So he was the first boyfriend I ever had where other bros thought I was cool because I was dating him."
Griffin previously opened up about their relationship in her 2009 book, Official Book Club Selection: A Memoir According to Kathy Griffin.
"Another example of getting flack [sic] from the boys is what happened when Jack Black dumped me," she wrote, per Goodreads. "Okay, we went out only two or three times, but that's a relationship in my book. And by the way, this is my book."
11 of 14
Drew Barrymore and Luke Wilson
Luke Wilson and Drew Barrymore attend the premiere of 'Blue Streak' at Mann Village Theater in L.A. on Sept. 13, 1999Credit: Ron Galella, Ltd./Getty Images
Luke Wilson and Drew Barrymore dated for a few years in the late '90s. Years later, the actress and talk show host told Kate Hudson in January 2022 that for at least some of their time together, it was an "open relationship."
Hudson — who was previously in a relationship with Luke's older brother and actor Owen Wilson — remembered meeting Barrymore for the first time while she was at dinner with Luke.
"I was dating him, but I think he was also dating other people. It was an open relationship; we were young," Barrymore responded, adding, "We're just young, we're having fun, we're all playing, acting, hanging out. You're not taking it all so seriously, and it was fun and we had the best time."
12 of 14
Owen Wilson and Sheryl Crow
Owen Wilson and Sheryl Crow attend the 'Shanghai Noon' premiere at Mann Chinese Theatre in L.A. on May 23, 2000Credit: Jim Smeal/Ron Galella Collection via Getty
Owen and then-girlfriend Sheryl Crow attended the 2000 premiere of Shanghai Noon. Per E! News, the pair began dating in 1999 after meeting on the set of The Minus Man — which marked the "Soak Up the Sun" singer's acting debut — and dated for two years.
Crow is now mom to her two sons, Wyatt and Levi. Owen, one of Hollywood's most famous bachelors, is a dad of three.
13 of 14
Jennifer Love Hewitt and Will Friedle
Will Friedle and Jennifer Love Hewitt at the 'I Know What You Did Last Summer' premiere in Hollywood, Calif., on Oct. 8, 1997Credit: Ron Galella, Ltd./Ron Galella Collection via Getty
Will Friedle was on deck to support Jennifer Love Hewitt at the 1997 premiere of I Know What You Did Last Summer in Hollywood.
The following year, Hewitt appeared on Friedle's show, Boy Meets World, as his character's love interest. While the episode might be a favorite among fans, Friedle said on an episode of the Pod Meets World podcast in November 2024 that the "super intense" makeout scene the two filmed is "uncomfortable" to watch now.
Hewitt shares three kids with husband Brian Hallisay, while Friedle is married to wife Susan Martens.
14 of 14
Michael Keaton and Courteney Cox
Michael Keaton and Courteney Cox attend NBC's winter press tour all-star reception at the Ritz Carlton Hotel in Pasadena, Calif., on Jan. 9, 1995Credit: SGranitz/WireImage
Michael Keaton and Courteney Cox were in a relationship from 1990 to 1995, during which time he took a second swing at playing Batman, and she joined Friends.
"It's the most important relationship I've ever had, and I think he's the most wonderful person I've ever met," Cox told PEOPLE right after their breakup.
on People
Source: “AOL Entertainment”
