The ’90s Were Peak Celebrity-Couple Energy — But Are They Still Friends Today?
The ’90s were peak “celebrity couple” energy, with paparazzi, red carpets, and relationships that became pop-culture landmarks. Some of these affairs ended quietly, some blew up the tabloids, and then there were a few who decided to give it a fair shot. But the part people always wonder about isn’t just how they got together — it’s what happened later.
Did your favorite ’90s couple stay friendly? Do they still talk in 2025, or did the relationship get filed away in the same mental drawer as dial-up internet, VHS tapes, and disposable cameras? Let’s find out.
1. Will Smith and Jada Pinkett Smith
They became one of the defining long-haul couples of the era and married in 1997, though Jada later said they had been living separately since 2016. Even so, recent reporting has described them as still “together” in the sense that they remain connected, involved in family life, and function as a team.
2. Reese Witherspoon and Ryan Phillippe
They met in 1997 and married in 1999, then split years later, but the co-parenting has continued for decades. In 2024, Phillippe posted a throwback photo with Witherspoon, and the accompanying reporting explicitly framed them as continuing to co-parent and show up together for major milestones in their children’s lives. He has also spoken publicly about putting the kids’ experience first as divorced parents.
3. Jennifer Lopez and Sean Combs
They dated from 1999 to early 2001, and he famously accompanied her during the era of the iconic green Versace dress incident. Years later, they were even photographed at the same event in 2018. As for keeping in touch, Combs publicly described Lopez as “just my friend” in 2021 — so, at least they’re not enemies.
4. Matthew McConaughey and Sandra Bullock
They got together after filming A Time to Kill (1996) and were seen together a few times by the paparazzi — nothing too wild. Years later, Bullock told Cosmopolitan (in a quote later recirculated by the outlet) that they stayed friends and that she expected they would remain close, regardless of where life took them.
5. Gisele Bündchen and Leonardo DiCaprio
They dated from around 2000 to 2005 and then went their separate ways. Bündchen has spoken about why the relationship ended, but she has not presented the breakup as the start of a continuing friendship. Are they still friends? Maybe just pen pals, at best? We honestly have no idea.
6. Liv Tyler and Joaquin Phoenix
Tyler and Phoenix were together as very young stars before splitting in 1998. However, they remained friends after the breakup. There is at least one instance of them being seen in public years later, when Tyler attended an event hosted by Phoenix and spoke about navigating that situation gracefully.
7. Winona Ryder and Johnny Depp
They were engaged in the early ’90s and split in 1993. Almost 17 years later, Ryder publicly defended Depp in a witness statement, as reported by People magazine. That’s not proof that they’re close today, but it does show she was willing to speak about his character many years after their relationship ended.
8. Tom Cruise and Nicole Kidman
They met on the set of Days of Thunder and married in 1990. The marriage lasted surprisingly long for a Hollywood couple, but they eventually divorced in 2001. Kidman has explained that she is reluctant to talk about the marriage publicly out of respect for those who came after — which is about all the public insight there is.
9. Ethan Hawke and Uma Thurman
Hawke and Thurman met while making Gattaca. They married in 1998 and divorced in 2005. Such is life. Thurman has said that she avoids speaking critically about her children’s father and focuses on keeping the peace. So yes, they do keep in touch — but no, it’s not as sweet as it once was.
10. Brad Pitt and Jennifer Aniston
This beloved couple met in 1998, married in 2000, and split in 2005, then spent years being treated like a national nostalgia project. After all that, Aniston has said that they are still “buddies,” that they speak, and that there’s “no oddness.” More recent sightings and appearances have also described Pitt as an important part of her life.
