With the Hollywood news cycle always full of new makeups, breakups, and matchups, it can be easy to forget about the showbiz relationships of the past. Here are some of the most iconic and buzzworthy A-list romances you might have forgotten, or never known about.
From Gwyneth Paltrow and Brad Pitt, to Angelina Jolie and Billy Bob Thornton, take a trip down memory lane and a look back at some of the linkups that once defined Tinseltown.
Ryan Reynolds & Alanis Morisette
Some fans forget that years the “Deadpool” star’s 2012 marriage to Blake Lively, Ryan Reynolds had a years-long relationship with Alanis Morisette. The pair was even engaged, according to The Daily Mail, which in January 2025 posted a resurfaced clip of the “You Oughta Know” singer talking about the end of her relationship with Reynolds.
Morisette did not reveal exactly what went on during the split, but said the incident inspired her to start attending therapy “five times a week.” She explained, “Therapy’s not about the guy, it’s about me.” The outlet says the two were an item from 2002 to 2007.
Jessica Biel & Chris Evans
Just Jared says Jessica Biel and Chris Evans paired up in 2001. They also shared the screen in two films, “London” and “Cellular.” The outlet says despite hinting in interviews at marriage potential, Biel and the “Captain America: The First Avenger” actor called things off in 2006.
Sandra Bullock & Matthew McConaughey
The “Miss Congeniality” star is alleged to have discreetly paired up with Texas native Matthew McConaughey in 1996 after meeting him on the set of “A Time To Kill,” per Cosmopolitan. Despite reportedly splitting in 1998, Bullock told the magazine in 2003 that she and the “Dallas Buyers Club” star would “always stay close.”
Sarah Jessica Parker & Robert Downey Jr.
Sarah Jessica Parker shared a seven-year relationship with “Iron Man” star Robert Downey Jr., according to US Weekly. The match-up began in the mid 80s and ended in 1991. The outlet called the relationship “tough” in a December 2024 report, recounting how Parker said in a 2016 interview on the “WTF With Marc Maron” podcast, “I just didn’t want him to die.”
Downey has since moved past the public struggles that plagued him until the early 2000s. The successful franchise star is now married to Susan Downey, with whom he shares three kids.
Gwyneth Paltrow & Brad Pitt
Gwyneth Paltrow and Brad Pitt are one of the most nostalgic couples of the 1990s. People says the pair, who dated from 1994 to 1997, have “remained friendly” after their split. “I adore him. He’s an amazing person, and he’s a great entrepreneur, and such a creative, and such a good person. I really love him. I’m a big fan,” the magazine quoted Paltrow as saying about Pitt in a May 2023 relationship rundown.
Ryan Seacrest & Julianne Hough
“DWTS” pro-turned-judge Julianne Hough was one of Ryan Seacrest’s most buzzed-about girlfriends. The ballroom beauty dated the “American Idol” host from 2010 to 2013, according to Newsweek. Hough appeared on a 2024 episode of “On Air With Ryan Seacrest,” proving the exes remain on friendly terms.
Angelina Jolie & Billy Bob Thornton
After years of dominating the headlines due to her super high-profile relationship, marriage, and divorce with Brad Pitt, the “Gia” actress’s relationship with Billy Bob Thornton can tend to be forgotten. However, it was big news at the time they dated. The pair, who met in 1999, had their biggest media moment when they made headlines for wearing vials of each other’s blood in 2001, per a 2024 People report.
Sandra Bullock & Ryan Gosling
Along with Ryan Reynolds, Sandra Bullock added “The Notebook” star Ryan Gosling to her list of A-list boyfriends. InStyle says they dated “low key” in 2002. The pair famously posed together on the red carpet at Cannes that year, but never officially spoke out to confirm the romance.
Winona Ryder & Christian Slater
Winona Ryder shared a short relationship with her “Heathers” costar Christian Slater way back in 1988. Johnny Depp has also been linked to the “Stranger Things” star has also been famously linked to the “Stranger Things” star, according to US Weekly. She is currently dating fashion designer Scott Mackinlay Hahn.
Matthew Perry & Julia Roberts
Vogue says Roberts and Perry met for the first time on the set of “Friends” when Roberts made a guest appearance as “Susie Underpants.” Perry only dated the “Pretty Woman” star for a matter of months before calling it off.
So why did Julia Roberts and Matthew Perry break up? The “Fools Rush In” actor offered an explanation for the split in his 2022 memoir, “Friends, Lovers, and the Big Terrible Thing.” He wrote of the relationship’s end, “âDating Julia Roberts had been too much for meâ¦So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts.â
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