10+ Couples From The Past That Leave Us Feeling Nostalgic

Britney Spears and Justin Timberlake. Jennifer Aniston and Brad Pitt.

Talk about a TBT!

These are just some of the star-studded celebrity couples that once were. Some have even rekindled their spark in 2021 (looking at you, Jen and Ben!).

Come take a walk down memory lane with these 10+ former couples that leave us feeling nostalgic.

1. Ben Affleck and Jennifer Lopez

Ah, Jen and Ben. If you can look past their movie Gigli, you'd see that they were an adorable couple.

They were together for 18 months and were even engaged during this time. Their romantic might even be rekindled these days...

Ever since Jennifer called off her engagement with Alex Rodriguez, she's been spotted hanging out with the *Batman* actor.

Sources say that they are full-on dating each other, very happy, and that it didn't take long for them to get comfortable again.

2. Britney Spears and Justin Timberlake

These two were a match in pop music heaven. They first got to know each other as kids on The Mickey Mouse Club and then made things official in 2000. TBH, we're still not over their 2002 breakup.

3. Ryan Gosling and Rachel McAdams

Anyone who has ever seen The Notebook knows that these two Canadian hotties had serious chemistry.

This is despite hating each other at the beginning of filming... After the movie, they dated for four years before calling it quits in 2008.

4. Demi Moore and Bruce Willis

The pair first met in 1987 at the premiere of action-comedy Stakeout. Demi was engaged at the time, but she broke up with her fiancé and she married Bruce four months later. They had three kids together but eventually divorced.

The former pair are surprisingly still close!

"We managed to move the heart of our relationship, the heart of what created our family, into something new that gave the girls a loving, supportive environment with both parents," Moore wrote in her memoir, Inside Out.

5. Kristen Stewart and Robert Pattinson

Our tween hearts couldn't take it when Bella and Edward became a thing IRL. They were so cute!

They even won MTV's "Best Kiss" award four years in a row! Sadly, their end was dramatic, as Stewart was caught cheating...

6. Jessica Simpson and Nick Lachey

Who could forget their MTV reality TV show, Newlyweds: Nick and Jessica? The pop singers were one of the most adorable pairs in the industry in the early '00s.

But just like their show was eventually canceled, so was their marriage.

7. Kirsten Dunst and Jake Gyllenhaal

These two made such an adorable couple. They even had a cute "how they met" story, as they were introduced by Jake's older sister, Maggie.

During their short two years together, they bought a house and even adopted a puppy.

8. Ryan Reynolds and Scarlett Johansson

Once upon a time, these two movie stars were married.

It feels like an infinity ago, but it was actually in 2008. Both have since happily remarried: Ryan to Blake Lively and Scarlett to Colin Jost.

9. Kim Basinger and Alec Baldwin

The pair met on the set of The Marrying Man in 1991.

Their real-life romance was pretty chaotic, just like their characters'. They ended up getting married in 1993 and welcomed a daughter. In 2002, they split.

10. Cindy Crawford and Richard Gere

What a gorgeous pair! At the time, the supermodel was considered one of the world's most beautiful women and Gere was a bonified movie star thanks to Pretty Woman.

They were actually married for four years before splitting in 1995.

11. Billy Bob Thornton and Angelina Jolie

Megan Fox's latest fashion antics with Machine Gun Kelly have reminded us of the weirdness that was Angelina's three-year marriage to Billy Bob.

When they were together, they would store each other's blood in vials around their necks...

12. Tom Cruise and Katie Holmes

It feels like just yesterday that Tom Cruise was jumping up and down on Oprah's couch over his love for Katie.

This passionate couple married in 2006 and welcomed one daughter together. They eventually divorced.

13. Elizabeth Hurley and Hugh Grant

After meeting on a Spanish film in 1987, they became one of England's most gorgeous couples.

Sadly, their 13 years together came to an end when Grant was arrested with a prostitute in 1995...

14. Johnny Depp and Winona Ryder

The pair were classic '90s vibes. Their style, their innocence. Depp even proposed after just five months of dating!

"There’s been nothing in my 27 years that’s comparable to the feeling I have with Winona,” he once told People about Ryder.

Sadly, the pair ended their engagement three years later in '93.

The exes are still close, though, as Winona has come to the defense of her ex as he battles domestic violence claims made by his ex-wife, Amber Heard.

15. Jennifer Aniston and Brad Pitt


And now, we come to this former power couple. The newly-dropped Friends reunion has reminded fans of the time Pitt made the audience go nuts during his guest appearance on the show.

At the time, the pair were married.

As the world knows, the couple had a rough split: they divorced following rumors that Brad had cheated on her with Angelina Jolie.

Despite everything, the former golden pair of the '90s have become great friends. We loved seeing them chat backstage at the 2020 SAG Awards!