Skip to content

Top Navigation

PEOPLE.com PEOPLE.com
  • News
    • Coronavirus
    • Crime
    • Human Interest
    • Politics
  • Entertainment
    • Celebrity
    • TV
    • Movies
    • Music
    • Country
    • Awards
    • Sports
    • Theater
    • Books
  • Coronavirus
  • Royals
  • Lifestyle
    • Style
    • Fashion
    • Beauty
    • Health
    • Parents
    • Home
    • Real Estate
    • Pets
    • Food
    • Shopping
    • Tech
  • PeopleTV
  • Shopping
    • Coupons

Profile Menu

Your Account

Account

  • Join Now
  • Email Preferences
  • Newsletters
  • Manage Your Subscription

More

  • Give a Gift Subscription
  • Premium
Login
Logout
Subscribe

Explore PEOPLE.com

PEOPLE.com PEOPLE.com
  • Explore

    Explore

    • Every Tiara Worn at a Royal Wedding

      From Princess Beatrice to Meghan Markle Read More Next
    • Engineer Creates App To Translate Your Cat

      Find out what your cat is trying to tell you with a new cat app Read More Next
    • The Sweetest Photos of Princes Harry with Diana

      Princess Diana died when Harry was just 12 years old Read More Next
  • News

    News

    See All News

    Sean Connery's Cause of Death Revealed Weeks After He Dies at Age 90

    Sean Connery died on Oct. 31 at age 90
    • Coronavirus
    • Crime
    • Human Interest
    • Politics
  • Entertainment

    Entertainment

    See All Entertainment

    Coyote Ugly Turns 20: Where Is the Cast Now?

    • Celebrity
    • TV
    • Movies
    • Music
    • Country
    • Awards
    • Sports
    • Theater
    • Books
  • Coronavirus
  • Royals
  • Lifestyle

    Lifestyle

    See All Lifestyle

    Introducing ... PEOPLE's Products Worth the Hype

    • Style
    • Fashion
    • Beauty
    • Health
    • Parents
    • Home
    • Real Estate
    • Pets
    • Food
    • Shopping
    • Tech
  • PeopleTV
  • Shopping

    Shopping

    • Coupons

Profile Menu

Subscribe this link opens in a new tab
Your Account

Account

  • Join Now
  • Email Preferences
  • Newsletters
  • Manage Your Subscription

More

  • Give a Gift Subscription
  • Premium
Login
Logout
Sweepstakes

Follow Us

People is on Community!
Text us for exclusive photos and videos, royal news, and way more.
Text: 212-479-1704
  1. People.com
  2. Celebrity
  3. 17 Throwback Celebrity Couple Photos So Good You Won't Be Able to Look Away

17 Throwback Celebrity Couple Photos So Good You Won't Be Able to Look Away

Take a look back at some of your favorite ex-couples and some you had no idea were even together
By Diane J. Cho
March 14, 2019 02:03 PM
Skip gallery slides
FB Tweet

1 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

Busy Philipps & Colin Hanks

Credit: Busy Philipps/Instagram

The actors dated in college when they were both students at Loyola Marymount University in the '90s and have since become friends.

“He was my college boyfriend!” Philipps said on Live with Kelly. “We met when I was 18 and Colin was 19… We are very very close friends now — his wife and I are tight, he and my husband hang out. We go on vacation together. He’s real excited that I’m here.”

1 of 17

Advertisement
Advertisement

2 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

Ashton Kutcher & January Jones

Credit: Ron Galella, Ltd./WireImage

The now famous and successful actress dated Kutcher back when she first arrived in L.A. to make a name for herself. Kutcher doubted that his then-girlfriend would make it in Hollywood and boy, was he wrong.

“[He] was not supportive of my acting,” Jones told GQ. “He was like, I don’t think you’re going to be good at this. So – f— you! He only has nice things to say now – if anything, I should thank him. Because the minute you tell me I can’t do something, that’s when I’m most motivated.”

2 of 17

3 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

Kelly Preston & George Clooney

Credit: Barry King/WireImage

Way before John Travolta and Amal Clooney were in the picture, the ex-couple dated for two years and even lived together until they broke up in 1989.

3 of 17

Advertisement
Continued on next slide.
Advertisement

4 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

David Gallagher & Megan Fox

Credit: Jim Spellman/WireImage

Once upon a time, these two teenage heartthrobs dated from 2003 to 2004 before going their separate ways. Is it safe to assume the teeny bopper in all of us is still mourning this relationship? We think yes.

4 of 17

Advertisement

5 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

Michael Keaton & Courteney Cox

Credit: Getty

The former Batman and Friends stars were in a serious relationship for five years until they split in 1995.

"It’s the most important relationship I’ve ever had," Cox told PEOPLE right after their breakup in the 90s, "and I think he’s the most wonderful person I’ve ever met.”

5 of 17

6 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

Ryan Phillippe & Reese Witherspoon

Credit: Victor Malafronte/Getty

The stars of Cruel Intentions took their on-screen romance off-screen and the two got engaged only a year after they met, in 1997 at Witherspoon's 21st birthday party. They got married in 1999 while the actress was six months pregnant with their daughter Ava, but announced their separation in 2006.

6 of 17

Advertisement
Advertisement
Continued on next slide.
Advertisement

7 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

Bruce Willis & Demi Moore

Credit: Ron Galella/WireImage

The ex-couple fell for each other hard and fast. In 1987, the two got married in Vegas only four months after they first met. During their up-and-down 11-year marriage, Willis and Moore welcomed three daughters, Rumer, Scout and Tallulah, but sadly called it quits in 1998.

7 of 17

Advertisement
Advertisement

8 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

Ryan Gosling & Sandra Bullock

Credit: Getty

The two quietly started dating while filming Murder by Numbers back in 2002. Their 16-year age difference made headlines but that didn't stop the actors from dating for more than a year before splitting in 2003.

8 of 17

Advertisement

9 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

Miley Cyrus & Nick Jonas

Credit: Kevin Mazur/WireImage

It was love at first sight for the two former child stars.

"We became boyfriend and girlfriend the day we met," Cyrus told Seventeen back in 2008. "He was on a quest to meet me, and he was like, ‘I think you’re beautiful and I really like you.’ And I was like, ‘Oh, my gosh, I like you so much.'"

The sweet romance ended after about a year and now they're all grown up. Cyrus is married to Liam Hemsworth and Jonas is married to Priyanka Chopra.

9 of 17

Advertisement
Advertisement
Continued on next slide.
Advertisement

10 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

Mila Kunis & Macaulay Culkin

Credit: Dimitrios Kambouris/WireImage

The actors dated from 2002 to 2011 and pretty much kept their relationship private from the public eye throughout its entirety. Then, almost a decade later, Kunis spoke about the couple's split on Dax Shepard's podcast, saying it was, "a horrible, horrible breakup. I f—— up."

10 of 17

Advertisement
Advertisement
Advertisement

11 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

Kevin Federline & Britney Spears

Credit: Kevin Mazur/WireImage

The two had a Chaotic two-and-a-half year marriage that resulted in their own reality series with the same name. They got quickly engaged, closely after Spears' 55-hour marriage to childhood friend Jason Alexander, and threw a surprise wedding in 2004. After a very messy marriage and a tough divorce, the two continue to battle over child support for their sons Sean Preston and Jayden James.

11 of 17

Advertisement
Advertisement

12 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

Cody Simpson & Gigi Hadid

Credit: Jim Spellman/WireImage

The singer and model dated for two years but after announcing their split in 2015, Simpson revealed that the decision was mutual.

"Cody and Gigi want each other to be in a place right now that allows him to only focus on his music, fans, and new message, while she can focus and continue building her career," Hadid’s rep told PEOPLE right after the breakup. "They remain friends with no hard feelings and each other’s biggest supporters."

12 of 17

Advertisement
Advertisement
Continued on next slide.
Advertisement

13 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

Zooey Deschanel & Jason Schwartzman

Credit: George Pimentel/WireImage

Schwartzman was Deschanel's first "real" boyfriend, according to Bustle. The two dated when they were both 19.

Now, Schwartzman is married to fashion designer Brady Cunningham and Deschanel is married to and just had her second child with film producer Jacob Penchenik.

13 of 17

Advertisement
Advertisement
Advertisement

14 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

Gwyneth Paltrow & Brad Pitt

Credit: Kevin Mazur Archive/WireImage

Paltrow and Pitt, the 90s "it" couple, dated for two years before they broke up in 1997. Both have since moved on but Paltrow opened up about how she was glad they dated when they did.

“I remember when Brad Pitt and I broke up, it was on the cover of the New York Post and there was no one outside my house,” she told WSJ Magazine. “That would never happen today.”

14 of 17

Advertisement
Advertisement

15 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

Lenny Kravitz & Nicole Kidman

Credit: Kevin Mazur/WireImage

Kidman revealed that she was once engaged to her Big Little Lies costar Zoë Kravitz's father, Lenny Kravitz. The engagement took place after her divorce from Tom Cruise and before her marriage to current husband Keith Urban. The actress told Vanity Fair that the secret engagement "just wasn't right" and that they were both not ready to take the next step.

15 of 17

Advertisement
Advertisement
Continued on next slide.
Advertisement

16 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

Jenna Dewan & Justin Timberlake

Credit: Frank Micelotta/ImageDirect

The two briefly dated while Dewan was backup dancing for the singer. They were friends first, then decided to date shortly after his breakup with Britney Spears but it didn't last very long.

16 of 17

Advertisement
Advertisement
Advertisement

17 of 17

FB Tweet
Pinterest Mail Email iphone Send Text Message

Jake Gyllenhaal & Kirsten Dunst

Credit: Jeff Vespa/WireImage

The actors were first introduced by Gyllenhaal's sister, Maggie, and began dating in 2002. They eventually moved in together and even adopted a German Shepherd mix puppy before splitting two years later.

17 of 17

Advertisement
Advertisement
Replay gallery

Share the Gallery

Pinterest Facebook

Up Next

By Diane J. Cho

Share the Gallery

Pinterest Facebook
Trending Videos
Advertisement
Skip slide summaries

Everything in This Slideshow

Advertisement

View All

1 of 17 Busy Philipps & Colin Hanks
2 of 17 Ashton Kutcher & January Jones
3 of 17 Kelly Preston & George Clooney
4 of 17 David Gallagher & Megan Fox
5 of 17 Michael Keaton & Courteney Cox
6 of 17 Ryan Phillippe & Reese Witherspoon
7 of 17 Bruce Willis & Demi Moore
8 of 17 Ryan Gosling & Sandra Bullock
9 of 17 Miley Cyrus & Nick Jonas
10 of 17 Mila Kunis & Macaulay Culkin
11 of 17 Kevin Federline & Britney Spears
12 of 17 Cody Simpson & Gigi Hadid
13 of 17 Zooey Deschanel & Jason Schwartzman
14 of 17 Gwyneth Paltrow & Brad Pitt
15 of 17 Lenny Kravitz & Nicole Kidman
16 of 17 Jenna Dewan & Justin Timberlake
17 of 17 Jake Gyllenhaal & Kirsten Dunst

Share options

Pinterest Mail Email iphone Send Text Message

Login

PEOPLE.com

Magazines & More

Learn More

  • Subscribe this link opens in a new tab
  • Advertise
  • Content Licensing
  • Sitemap
  • Student Offer this link opens in a new tab

Connect

People is on Community!
Text us for exclusive photos and videos, royal news, and way more.
Text: 212-479-1704
Newsletter Sign Up
Other Meredith Sites

Other Meredith Sites

  • 4 Your Health this link opens in a new tab
  • Allrecipes this link opens in a new tab
  • All People Quilt this link opens in a new tab
  • Better Homes & Gardens this link opens in a new tab
  • Bizrate Insights this link opens in a new tab
  • Bizrate Surveys this link opens in a new tab
  • Cooking Light this link opens in a new tab
  • Daily Paws this link opens in a new tab
  • EatingWell this link opens in a new tab
  • Eat This, Not That this link opens in a new tab
  • Entertainment Weekly this link opens in a new tab
  • Food & Wine this link opens in a new tab
  • Health this link opens in a new tab
  • Hello Giggles this link opens in a new tab
  • Instyle this link opens in a new tab
  • Martha Stewart this link opens in a new tab
  • Midwest Living this link opens in a new tab
  • More this link opens in a new tab
  • MyRecipes this link opens in a new tab
  • MyWedding this link opens in a new tab
  • My Food and Family this link opens in a new tab
  • MyLife this link opens in a new tab
  • Parenting this link opens in a new tab
  • Parents this link opens in a new tab
  • People en Español this link opens in a new tab
  • Rachael Ray Magazine this link opens in a new tab
  • Real Simple this link opens in a new tab
  • Ser Padres this link opens in a new tab
  • Shape this link opens in a new tab
  • Siempre Mujer this link opens in a new tab
  • Southern Living this link opens in a new tab
  • SwearBy this link opens in a new tab
  • Travel & Leisure this link opens in a new tab
© Copyright 2021 Meredith Corporationthis link opens in a new tab. People is a registered trademark of Meredith Corporation All Rights Reserved. People may receive compensation for some links to products and services on this website. Offers may be subject to change without notice. Privacy Policythis link opens in a new tab Terms of Servicethis link opens in a new tab Ad Choicesthis link opens in a new tab Manage Push Notificationsthis link opens in a new tab California Do Not Sellthis link opens a modal window Web Accessibilitythis link opens in a new tab

Manage Push Notifications

If you would like to opt out of browser push notifications, please refer to the following instructions specific to your device and browser: Google Chrome and Android, Firefox, Safari, or Microsoft Edge.
© Copyright . All rights reserved. Printed from https://people.com

View image

17 Throwback Celebrity Couple Photos So Good You Won't Be Able to Look Away
this link is to an external site that may or may not meet accessibility guidelines.