Hollywood couples are notorious for short-term relationships — Hello, Britney Spears and Jason Alexander coming in as the briefest at 55 hours! It seems like every other day, we hear that the couple that just walked the red carpet hand-in-adoring-hand is now heading for Splitsville. *Cough, Ben and J-Lo. Cough.*

Yet when we look back at those retro celebrity couples from the 60s, 70s, 80s, 90s, and beyond, many people have no clue that these A-listers even dated — much less were engaged!

So let’s take a stroll down memory lane and see which of your favorite Hollywood A-listers from back-in-the-day actually dated and, in many cases, almost tied the knot.

Demi Moore and Emilio Estevez

A long, long time ago, in a faraway land called the 1980s, two members of The Brat Pack were engaged. The Breakfast Club star and the St. Elmo’s Fire actress were once madly in love and couldn’t keep their hands off each other if they tried.

Sadly, according to Moore in her 2019 memoir Inside Out, her then-fiance, Estevez, got a wandering eye. When she eventually found out that he’d been cheating on her and got another woman pregnant, she ended their engagement.

Apparently, the pair may have made a truce because they went on to work together again in the 2006 film Bobby.

Ashton Kutcher and Brittany Murphy

Before Brittany Murphy’s tragic death in 2009, she and Ashton Kutcher were utterly obsessed with one another. The Just Married co-stars met on the set of this rom-com film but sparks continued to fly when the cameras stopped rolling.

Although they only lasted for a few months, the pair were snapped wearing matching wedding bands on shared outings. When Murphy passed away, Kutcher had nothing but praise for his former flame, telling ABC news that whenever she’d enter a room, she was “always the first person to dance.”

According to the That ‘70s Show star, he likes to carry the lessons she taught him about life to this very day.

Robert Downey Jr. and Sarah Jessica Parker

Many people are unaware that Iron Man and Carrie Bradshaw — uh, we mean Robert Downey Jr. and Sarah Jessica Parker — were once engaged. The couple dated for eight years, owned a pet cat, and lived together in Charlie Chaplin’s former home in Los Angeles.

Although they currently have nothing but love and respect for each other now, SJP eventually called it quits due to the Marvel star’s struggle with drug and alcohol addiction. The Sex and the City star did everything she could to help RDJ get sober, yet she says the relationship eventually began to feel more like that of a mother and son than a romantic couple.

Rob Lowe and Winona Ryder

Believe it or not, the Parks and Rec actor and the Stranger Things star were once reported to have been an item. Back in the late 80s, before Winona Ryder became one of the most well-paid starlets on the planet, she and Rob Lowe were rumored to be romantically involved.

The pair met after starring in the 1987 film, Square Dance. Although the film met with poor ratings, it brought the two together and forged a way for Ryder’s Hollywood career.

Both have found enduring relationships since then, with Lowe married to makeup artist, Sheryl Berkoff, since 1991. Meanwhile, Ryder has been linked to longterm boyfriend, Scott Mackinley Hahn since 2011.

Jeff Goldblum and Laura Dern

Did you know that these Jurassic Park co-stars — Jeff Goldblum and Laura Dern — were engaged to be married in the 1990s? Yep, you’ve read that right. Sparks flew between the Wicked actor and the Big Little Lies star way back while they shot the epic dinosaur film.

Despite their fifteen-year age difference, the two seemed incredibly happy together while appearing at premiere parties and red carpet events. Although they eventually called off their relationship, it appears to be water under the bridge. In 2020, they joined forces again by reuniting for Jurassic World.

Frank Sinatra and Marilyn Monroe

Taking it way back to the 1950s, most people are totally unaware of how smitten by each other Frank Sinatra and Marilyn Monroe were. Although they never officially dated as “boyfriend” and “girlfriend,” the best way to describe their romance in modern terms would be “situationship.”

While the “Fly Me To The Moon” crooner was known for being a big ol’ lifelong womanizer, he couldn’t bring himself to hurt Marilyn since. He saw Marillyn as particularly vulnerable and “fragile” at that time in her life. He looked after the Hollywood Icon and even planned on proposing to Monroe since he could sense her downward spiral only weeks before her tragic death.

Monroe’s ex-husband, Joe DiMaggio refused to allow Frank Sinatra to attend her funeral. “I loved her too,” Sinatra allegedly confessed. “No one can say I didn’t love her, too.”

Winona Ryder and Johnny Depp

The Edward Scissorhands co-stars — Johnny Depp and Winona Ryder — had a passionate engagement shared from 1989-1993. The Pirates of the Caribbean star was so enamoured with Ryder that he famously got a tattoo which said “Winona Forever.”

Although they ended their engagement, they still speak fondly of each other whenever they get the chance. The Stranger Things star even defended her former fiance in the 2022 Amber Heard-Johnny Depp defamation case. According to Ryder, Depp was her first true love.

Matthew Broderick and Jennifer Grey

Although Matthew Broderick and Jennifer Grey famously played siblings in the 80s hit classic Ferris Bueller’s Day Off, the two were romantically involved behind the scenes. According to Grey, they kept their relationship a secret while filming and then went public following the movie’s release.

The pair dated for a short while in the 1980s, yet called it quits following a tragic car accident which left both traumatized.

Later, Broderick would go on to marry Sarah Jessica Parker. Interestingly enough, the Dirty Dancing star got engaged to Johnny Depp just a few months later!

Aubrey Plaza and Michael Cera

Did you know that the Scott Pilgrim vs. The World stars — Michael Cera and Aubrey Plaza — dated? The pair almost tied the knot as a part of a practical joke while in Las Vegas. Both comedic actors are known for their lovably awkward/introverted personalities. So it’s not all that shocking that they’d gravitate towards one another.

At one point, they actually planned on getting married for the sole purpose of getting divorced. (It turns out their real-life personas are just as strange as their on-screen characters. And honestly, we love them all the more for it.)

Molly Ringwald and Anthony Michael Hall

While in The Breakfast Club, Molly Ringwald’s character wins the heart of bad-boy Bender. But behind the scenes, the beauty only had eyes for the geek. After starring in the John Hughes classic, Molly Ringwald and Anthony Michael Hall dated while at the height of their Brat Pack fame.

Although they insist it was a “puppy love” sort of dynamic, they’ve carried a torch for each other and are friends to this day. Aww!

Mila Kunis and Macaulay Culkin

Before the That ‘70s Show actress tied the knot with her former co-star, Ashton Kutcher, Mila Kunis was in a long-term relationship with Home Alone’s Macaulay Culkin The pair dated for close to a decade.

Despite both being massive Hollywood stars, they decided it was best to keep their relationship on the down low and refused to spill the deets about their personal lives for the tabloids. What we do know, though, is that Kunis ended their long-term romance in what she confessed on the Armchair Expert podcast to be a “horrible” breakup. Ouch!

Timothee Chalamet and Madonna’s Daughter, Lourdes

Before Timothee Chalamet became one of the most smashing boy celebs in the world, the Call Me By Your Name star was in a relationship with Madonna’s daughter, Lourdes Leon. The pair dated while attending high school together at Laguardia. How cute!

Nowadays, the Dune star is in a relationship with Kylie Jenner. Meanwhile, Lourdes is following in her mother’s footsteps by pursuing her own music career.