Celebrities you definitely forgot dated

Remember when Gossip Girl met real life?

Author: Siam Goorwich and Alex RossPublished 10th Feb 2022

Think you know who's dated who in the world of showbiz? Think again...

Whilst we all know about the celeb super couples who give us serious relationship goals, and those that we just didn't see coming, these lot have gone to the back of our memories, so with Valentine's Day fast approaching, what a better to time to dig into the celebrity couple archives?!

From Gossip Girl stars Blake Lively and Penn Badgley, to the time Madonna dated Tupac, take a trip down memory lane at all of the celebrity couples you totally forgot about.

Celebrity couples we totally forgot about:

Blake Lively and Penn Badgley

Long before Blake was ultimate #CoupleGoals with hubby Ryan Reynolds, she made Gossip Girl fans' dreams come true by dating her GG co-star Penn Badgley. Sadly the couple broke everyone's hearts by splitting up three years later, but we think we can all agree it was for the greater good.

Cameron Diaz and Justin Timberlake

Cameron Diaz and Justin Timberlake began dating after meeting at the Nickelodeon Kids' Choice Awards in 2003. The couple dated for almost four years, and appeared to spend much of their relationship looking loved-up at sports events.

Mila Kunis and Macaulay Culkin

And the award for the cutest celeb couple of all time is... Mila Kunis and Macaulay Culkin. Seriously, just look at them!


Of course, it didn't last and now Mila is married to Ashton Kutcher.

Jennifer Aniston and Owen Wilson

Jennifer and Owen dated for a short time in 2008 after filming Marley & Me together.

Madonna and Tupac

Believe it or not, Madonna actually dated American rapper Tupac Shakur after the pair were introduced by Rosie Perez at the 1993 Soul Train Awards.


Albeit a very short-lived romance, the late rapper's brother confirmed they once dated, saying, "I don't think it was super serious, gonna get married or some s--t. You know how those entertainment relationships go. But they both respected each other, so it ended cool. He never talked s--t about her, not to me. And she never talked s--t about him."

Keira Knightley and Jamie Dornan

Long before he was dark and brooding and Christian Grey, Jamie Dornan was the dark, brooding boyfriend of Keira Knightley.

Johnny Depp and Kate Moss

We don't want to be dramatic, but Kate Moss and Johnny Depp were probably the hottest couple OF ALL TIME.


The couple met in 1994 - when Johnny was 31 and Kate was 20 - and dated for four years and were reportedly even engaged.

Sandra Bullock and Matthew Mcconaughey

Sandra Bullock and Matthew Mcconaughey became a couple after starring in A Time To Kill together. Despite the fact they looked SUPER CUTE together with their matching glossy curls, their relationship lasted less than two years.

Seal and Tyra Banks

Before Seal married Heidi Klum and started throwing THE BEST Halloween parties of all time, he briefly dated model and 'smize' enthusiast Tyra Banks.

Kirsten Dunst and Jake Gyllenhaal

Brace yourselves, ladies, for you're about to witness pictures of dreamboat Jake Gyllenhaal looking TOTALLY besotted with another woman. The woman in question is, of course, Kirsten Dunst, who he dated from 2002 - 2004.

Kate Bosworth and Orlando Bloom

Long before he started a family with Katy Perry, British actor Orlando Bloom dated super-chic actress Kate Bosworth.

Sandra Bullock and Ryan Gosling

Yes, much to everyone's surprise, Ryan Gosling and Sandra Bullock were once a 'thing'. Briefly.

Alec Baldwin and Kim Basinger

Kim Basinger and Alec Baldwin were married for nine years and have one child - Ireland Baldwin - together. Sadly, their relationship ended in a bitter divorce in 2002.

Gwyneth Paltrow and Brad Pitt

Can we all just take a moment to remember just how great Gwyneth Paltrow and Brad Pitt were together. Look - they even had matching hair! The couple, who were together from 1994 - 1997 met when Gwynnie was just 24, and were even engaged. Talking about the relationship years later, Oscar winner Gwyneth admitted: "I f----- that up, Brad!" REGRETS!

Gwyneth Paltrow and Ben Affleck

Who do you possibly date if you've just broken up with Brad Pitt? Well, if you're Gwyneth Paltrow, that answer's Ben Affleck. The couple dated on and off till 2000.

Kim Kardashian and Nick Cannon

Back when Kim Kardashian was BFFs with Paris Hilton, she was dating Nick Cannon - aka. Mariah Carey's baby daddy.

Ashton Kutcher and January Jones

Before we all knew her as Betty Draper in Mad Men, January Jones dated Ashton Kutcher. The couple dated from 1998 - 2001, but sadly, despite the fact they look seriously happy in this snap, it turns out Ashton was a bit of a jerk. Talking to GQ in 2009, January admitted, "He was not supportive of my acting... He was like, 'I don't think you're going to be good at this."

Chris Evans and Jessica Biel

Yes, Jessica Biel (who's now happily to married to Justin Timberlake) used to date Captain America! Sorry, we mean, Chris Evans. Who knew?

Madonna and Sean Penn

Madonna's dating history is long and varied - from legendary artist Jean Michel Basquiat to, er, Vanilla Ice - but let's take a minute to remember that her first husband was none other than Sean Penn. The couple were married from 1985 - 1989.

Jennifer Lopez and Wesley Snipes

J-Lo has had some hot, and seriously famous ex's (Diddy, Marc Anthony, Ben Affleck!), but did you know she briefly dated actor Wesley Snipes in the mid-90s? No, neither did we!

Owen Wilson and Sheryl Crow

Owen Wilson dated 'All I Wanna Do' singer Sheryl Crow from 1999 - 2001. Here they are having a red carpet snog.

Courteney Cox and Michael Keaton

Courteney Cox and Michael Keaton dated for an impressive (in Hollywood terms, at least) six years. Following their split in 1995, Courteney said. "It's the most important relationship I've ever had, and I think he's the most wonderful person I've ever met." Awww!

Jennifer Aniston and Vince Vaughn

Remember when Jennifer Aniston dated Vince Vaughn? The couple started dating after filming The Break Up together (which was possibly a bad omen) because, as you can see from this snap of them not enjoying each other's company, it wasn't really #CoupleGoals

Ryan Reynolds and Alanis Morissette

Does Ryan Reynolds and Alanis Morisette strike anyone else as a bit of an odd coupling? Yes, we know they're both Canadian, but still. Anyway, the couple dated for five long years after meeting at Drew Barrymore's birthday party in 2002, and were even engaged to be married.

George Clooney and Lucy Liu

George Clooney's dated more gorgeous women than we've had hot dinners, but we were particularly into his short-lived fling with Charlie's Angels star Lucy Liu.

Cameron Diaz and Jared Leto

Look at these cool kids! Yep, Cameron Diaz and Jared Leto dated from 1999 - 2003 and were reportedly even engaged.

Nicole Kidman and Lenny Kravitz

Despite the fact that Nicole Kidman and Lenny Kravitz dated for two years (2003 - 2005) and were even engaged, the only photos we could find of the pair was this seriously awkward encounter with Nicole's now hubby Keith Urban.

Sarah Jessica Parker and Robert Downey Jr.

Yes, that is Robert Downey Jr. And yes, he dated Sarah Jessica Parker - for an incredible seven years in fact! We love this snap of them looking seriously cute back in 1990!

Jennifer Aniston and Tate Donovan

Before Brad, Jennifer Aniston dated Tate Cooper- who you'll probably know as Jimmy Cooper, Marissa's hot dad in The O.C.

Tom Cruise and Penelope Cruz

Who can forget the time that Tom Cruise and Penelope Cruz began dating and everyone REALLY hoped they'd get married and double barrel their names #Mems

Stacey Solomon and Steve-O

Following the release of Jackass Forever, fans were reminded of that time back in 2015 when former X Factor star Stacey Solomon dated none other than the crazy dare-devil himself, Steve-O. The pair enjoyed a six-month relationship after meeting on Channel 4 show The Jump.

Well, that was a blast from the past!

Now read:

Reality TV couples you completely forgot dated

Celebrity couples that give us relationship goals

Celebrity couples that shocked the world of showbiz

How to listen to Downtown Radio:

Tune into Northern Ireland's Home of Great Music, Downtown Radio on FM, AM, DAB Digital Radio, online, on our Rayo app and by asking your smart speaker to 'Play Downtown Radio'. Gary & Glen kick things off every weekday morning and Neal McClelland brings you home on Downtown Drive.