Advertisement

Close this content

40 Celebrities You Forgot Dated at One Time

Men's Health

July 19, 2020 at 9:05 AM

40 Celebrities You Forgot Dated at One Time

Penelope Cruz and Tom Cruise

Rachel McAdams and Michael Sheen

Mila Kunis and Macaulay Culkin

Alanis Morrissette and Ryan Reynolds

Cameron Diaz and Justin Timberlake

Zachary Quinto and Jonathan Groff

Christina Applegate and Brad Pitt

Cindy Crawford and Richard Gere

Salma Hayek and Edward Norton

Anjelica Huston and Jack Nicholson

Tom Cruise and Cher

Ryan Gosling and Sandra Bullock

Sandra Bullock and Matthew McConaughey

Janet Jackson and Matthew McConaughey

Tyra Banks and Drake

Ashton Kutcher and January Jones

Brooke Shields and Nicolas Cage

Courteney Cox and Michael Keaton

Kim Kardashian and Nick Cannon

Shia LaBeouf and Hilary Duff

Jared Leto and Cameron Diaz

Jennifer Aniston and Paul Rudd

Justin Timberlake and Fergie

Jenna Dewan and Justin Timberlake

Leonardo DiCaprio and Gisele Bündchen

Josh Hutcherson and Vanessa Hudgens

Joaquin Phoenix and Liv Tyler

Matt Damon and Winona Ryder

Luke Wilson and Gwyneth Paltrow

Madonna and Michael Jackson

David Arquette and Drew Barrymore

Heather Graham and Matthew Perry

Miley Cyrus and Nick Jones

Alexis Bledel and Milo Ventimiglia

Kristen Johnson and Ryan Reynolds

Natalie Portman and Jake Gyllenhaal

Sarah Jessica Parker and Michale J. Fox

Sarah Jessica Parker and Robert Downey Jr.

Jennifer Lopez and Diddy

Kate Hudson and Alex Rodriguez

40 Celebrities You Forgot Dated at One Time

When it comes to Hollywood, there's a lot of celebrity breakups and divorces, and it can be hard to keep up. Remember when Jenna Dewan and Channing Tatum posted a heartbreaking Instagram announcing their divorce? Or the ongoing mystery of Bella Hadid and the Weeknd? The sad trend has us reminiscing about the times when some of our other favorite Hollywood A-listers used to go out, and...actually, things turned out okay for them. Click through for a trip down memory lane with the stars you totally used to ship.

Getty Images

Some major throwbacks ahead.

From Men's Health

Yahoo Sports
Timberwolves coach Chris Finch calls Jamal Murray's heat-pack toss on court 'inexcusable and dangerous'
Murray made a bad night on the court worse during a moment of frustration on the bench.
Yahoo Sports
Former NBA guard Darius Morris dies at 33
Former NBA guard Darius Morris has died at the age of 33. He played for five teams during his four NBA seasons. Morris played college basketball at Michigan.
Yahoo Finance
The FDIC change that leaves wealthy bank depositors with less protection
Affluent Americans may want to double-check how much of their bank deposits are protected by government-backed insurance. The rules governing trust accounts just changed.
Yahoo Finance
Former House Speaker Paul Ryan says he’s not voting for Trump : 'Character is too important'
Ryan says he would be writing in a Republican candidate instead of voting for Donald Trump.
Yahoo Sports
Ranking the best situations for the rookie quarterbacks: Start with Michael Penix in Atlanta at No. 1
It’s key to note that we’re not saying the “best team” or “best roster.” Instead, we’re talking about the best confluence of factors that can outline a path for survival and then success.
Yahoo Sports
Phil Mickelson on the majors: 'What if none of the LIV players played?'
Phil Mickelson hints that big changes could be coming to LIV Golf's rosters, and the majors will need to pay attention.
Yahoo Sports
Blockbuster May trade by Padres, MVP Ohtani has arrived, Willie Mays’ 93rd birthday & weekend recap
Jake Mintz & Jordan Shusterman discuss the Padres-Marlins trade that sent Luis Arraez to San Diego, as well as recap all the action from this weekend in baseball and send birthday wishes to hall-of-famer Willie Mays.
Yahoo Sports
Heat's Pat Riley unhappy with Jimmy Butler's remarks on Celtics and Knicks, implies he needs to play more
Miami Heat president Pat Riley rebuked comments Jimmy Butler made about the Boston Celtics and New York Knicks, while also implying that his star needs to play more.
Yahoo Sports
NBA playoffs: Officials admit they flubbed critical kick-ball call in controversial final minute of Pacers-Knicks
Tuesday's last-2-minute report should be interesting.
Yahoo Finance
Social Security just passed Medicare as the government's most pressing insolvency risk
An annual government report offered a glimmer of good news for Social Security and a jolt of good news for Medicare even as both programs continue to be on pace to run dry next decade.