You’re not supposed to dwell on the past, but when it comes to ill-fated celebrity relationships, we are all guilty of wishing we could go back in time and change the outcome.
Can you just imagine how different things would be if Jennifer Aniston and Brad Pitt’s marriage had stood the test of time? Or if Britney Spears had walked down the aisle for Justin Timberlake? The possibilities are endless when it comes to what could have been.
With that in mind, let us indulge you with some of the most iconic couples from the past who we all wish were still together…
1. Johnny Depp & Winona Ryder
Johnny Depp has dated a string of highly-coveted women throughout his life, but none of his former flames can rival Winona Ryder. Depp proposed to the Beetlejuice actress, who is eight years his junior, in July 1990. But they’d never marry, and three years later, they separated – which was rather awkward for the Edward Scissorhands actor who’d had “WINONA FOREVER” tattooed prominently on his arm.
2. Rachel McAdams & Ryan Gosling
Ryan Gosling may now be happily married to Eva Mendes, but there are still those who wish that it’d worked out between him and his The Notebook co-star, Rachel McAdams. Of course, the relationship between the Canadian duo was doomed from the outset, given that they both intensely hated each other whilst filming the steamy romance hit, The Notebook. In fact, the pair disliked each other so much that Gosling tried to have McAdams kicked off the set.
Despite this contempt for one another in a professional capacity, there was undeniable chemistry for they went on to date on and off for the next four years before finally calling it quits in 2008.
3. Justin Timberlake & Britney Spears
In the early noughties, Justin Timberlake and Britney Spears were to the music industry what Beyoncé and Jay-Z are today – if not more. The pop star pair first met in 1992 when they were cast alongside each other (and the aforementioned Ryan Gosling) in Disney’s The Mickey Mouse Club. By 2000, the pair announced they were dating and from that moment on they became Hollywood’s hottest couple. Sadly, it would all come crumbling down three years later.
After their breakup, Timberlake released his smash hit single ‘Cry Me A River’, which was reportedly about his romance with the pop princess. The lyrics seem to suggest that Spears cheated on the NSYNC heartthrob, but to this day, the real reason for their breakup remains unknown.
4. Jennifer Anniston & Brad Pitt
When Hollywood hunk Bradd Pitt married Friends star Jennifer Aniston in 2000, the world celebrated. Despite Tinseltown’s most eligible bachelor now being off the market, nobody could deny that they weren’t happy he’d found Aniston.
Of course, that would all come crashing down in 2005 when he starred in the high-intensity action film Mr. & Mrs. Smith with Angelina Jolie. Whilst on set, the two fell in love and, as a result, Aniston was pushed aside. They divorced that year, and just weeks later, Pitt was seen canoodling with Jolie.
But now, 22 years later, both Pitt and Aniston are single again after divorcing their significant others. Could a reunion be on the cards?
5. Angelina Jolie & Billy Bob Thornton
Before she snagged Pitt, Jolie was in an intense relationship with the actor, Billy Bob Thornton. Their 20 year age gap was frowned upon by many in Hollywood, but it was difficult to argue that they weren’t compatible. Their eccentric romance was highly-publicized, mainly given the fact that Thornton had been married four times prior to dating Jolie – in fact, he was engaged to be married to Jurassic Park star, Laura Dern, before dumping her in 1999 to marry Jolie the following year.
During their two-year marriage, the pair were known to wear vials of each other’s blood in lockets around their necks.
6. Jude Law & Sienna Miller
Sienna Miller and Jude Law had a rough ride in the media when they announced that they were dating. Their relationship was highly scrutinized – a pressure which only intensified on Christmas Day 2004 when they declared that they were engaged. But just one year later, it would end in tears when Law was forced to publicly apologize to Miller for having an affair with their children’s nanny – clearly, the tabloids knew something they didn’t!
7. Lenny Kravitz & Lisa Bonet
On her 20th birthday, The Cosby Show star, Lisa Bonet, made headlines when she eloped with the singer, Lenny Kravitz, who was three years her senior. The pair welcomed their daughter, Zoe Kravitz, the following year. For the next five years, the duo’s relationship would be the envy of people everywhere. Which made it especially difficult when they went their separate ways in 1993.
Bonet is now married to Aquaman hunk, Jason Momoa and since 1993, Kravitz has been romantically linked to Vanessa Paradis, Victoria’s Secret model Adriana Lima and Nicole Kidman.
8. Jennifer Lawrence & Nicholas Hoult
Lawrence and Hoult began dating after starring together in X-Men: First Class in 2010. At the time, Lawrence hadn’t yet appeared in highly popular The Hunger Games franchise. Over the following years, Lawrence’s career took off and Hoult also had several big roles to occupy himself with. Ultimately, their hectic schedules would leade the pair to separate in 2014 shortly after finishing filming X-Men: Days of Future Past.
9. Jake Gyllenhaal & Kristen Dunst
Dunst and Gyllenhaal dated for two years, before separating in 2002 when Dunst went on to star as Mary Jane in the Spider-Man franchise. After their break up, Gyllenhaal would go on to date a string of A-list stars, including Reese Witherspoon and Taylor Swift.
Despite their romance only being short-lived, nobody can ever forget the iconic paparazzi photos of the pair out for a meal in London, where Gyllenhaal looked utterly repulsed by the way Dunst tackled her salad!
10. Liam Neeson & Brooke Shields
Brooke Sheilds was the poster girl of the ’80s and ’90s. In fact, the young model was so desirable that she had A-list stars practically queuing to date her. One of those stars was Liam Neeson, who dated Shields in 1992 after wooing her with his “brogues, his poetry and his shi**y choice of cheap pinot grigio wine.”
They grew very serious and after just three months, he proposed – without a ring. Then, whilst spending Christmas together in New York, he flew to Los Angeles on a last-minute trip and never called her again.
“He came back after the first time he left me and asked me to marry him again,” Shields told People. “I said, ‘No, no, no, because knowing you, you’ll probably fall in love with your next leading lady and marry her, so I’m leaving myself out of this.’ And I was dead right.” Neeson went on to marry an actress, Natasha Richardson, in 1994.
11. Vanessa Hudgens & Zac Efron
Zac Efron and Vanessa Hudgens were total unknowns until they starred alongside one another in Disney’s smash hit High School Musical. Overnight, they became two of the most popular people in Hollywood – something only intensified by the fact that they became a couple off-screen as well as on.
Despite a lot of promise for their blossoming romance, the pair would separate in 2010, shortly after nudes of Hudgens were leaked online in two separate incidents.
12. Nina Dobrev & Ian Somerhalder
The chemistry on the set of The Vampire Diaries was clear between Nina Dobrev and Ian Somerhalder, so it was no surprise when they started dating in real life. The pair were the epitome of #RelationshipGoals from 2010 until their split in 2013. Afterwards, Dobrev left The Vampire Diaries and Somerhalder went on to marry Twilight star, Nikki Reed.
13. Rose McGowan & Marilyn Manson
Marilyn Manson’s relationship with Rose McGowan was synonymous for eccentricity. The pair were engaged from 1999 to 2001 before McGowan called off their marriage due to “lifestyle differences.”
14. Anna Faris & Chris Pratt
Faris and Pratt fell in love whilst playing love interests in the 2007 movie, Take Me Home Tonight. The following year they were engaged and the year after that they tied the knot in a secret ceremony in Bali.
Despite seeming to be the perfect Hollywood couple, the pair announced their divorce in December 2017. The news caused an outcry online with Twitter users begging them to get back together.
15. Nicole Kidman & Tom Cruise
Despite the fact that she’s now happily married to Keith Urban, Nicole Kidman’s marriage to Tom Cruise is still a pop culture phenomenon. The pair met in November 1989 whilst filming Days of Thunder and by Christmas Eve the following year, they were married. Despite adopting a son and daughter together, the ‘power couple’ announced their intention to divorce in 2001.
The details of their divorce remain unclear, with Kidman claiming to still love the actor in a 2006 interview with Ladies’ Home Journal. “He was huge; still is. To me, he was just Tom, but to everybody else, he is huge. But he was lovely to me and I loved him. I still love him,” she said.
Many speculate that the pair’s divorce was largely due to Cruise’s dedication to the Church of Scientology. In fact, in 2015 a former Church of Scientology executive came forward to say that he had been instructed to break the couple apart.