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.