So many Hollywood marriages and relationships are over and done before the ink on the gossip mags is dry, and in a lot of cases the splits aren’t a huge surprise. Relationships in the limelight are notoriously difficult to maintain—just listen to a Taylor Swift song—though there are a few couples who have stayed together for decades. Still, when certain celebrity pairings happen they become ultimate couple goals, which makes their fans take their breakups almost personally. It’s easy to become emotionally invested in the idea of happily ever after for them. And do we have to pick a side? Is it weird to root for a reunion? Here are 17 celeb couples who loved, and then lost.
The charming Parks & Recreation star and Arrested Development star started dating in 2000 and instantly seemed like a well-suited match. The powerhouse comedy duo got married in 2003, and had two children together before splitting in 2012.
This quirky couple seemed liked a perfect fit. They met on the set of the movie Take Me Home Tonight in 2007 and got married in 2009. There was an Instagram post about him braiding her hair that made fans swoon and it seemed like they would go the distance, but the duo separated in 2017.
The dancing duo met on the set of the movie Step Up in 2006 (way before Magic Mike), and got married in 2009. The hot couple had a daughter before separating in 2018 and divorcing in 2019.
Gen-X kids were thrilled when the Edward Scissorhands stars started dating in 1989. He got a tattoo that said “Winona Forever,” which seemed like the most romantic gesture, before they split up in 1993. (It now says “Wino Forever.”)
He was the dreamy older star of American Gigolo and Pretty Woman and she was the hottest supermodel on the planet. It was a beautiful ’90s romance, like something out of a movie. The two met in 1988, married in 1990 and divorced in 1995.
Still hoping this one works out, actually! The Dodgeball stars met in 1999 and got married a year later in Hawaii. They have two kids together, but announced their separation in 2017. But the two have been spotted multiple times together since looking adorably normal. So either they have the most amicable split ever, or there are still some sparks there. Fingers crossed.
When Bruce and Demi met, she was engaged to Emilio Estevez. After ending her engagement, Bruce and Demi had a whirlwind courtship, got married, and had their first daughter all in what seemed like the blink of an eye. The pair were together for another decade (and had two more children) before shocking the tabloids with their divorce in 2000. But even though their split was sad at first, the two have gone on to demonstrate how to co-parent and be friends post-divorce. They’ve supported each other through all their other relationships, and even had some family quarantine time together during the COVID-19 pandemic.
The hot young couple met at her 21st birthday party in 1997, two years before they steamed up the screen in Cruel Intentions. They married in 1999, when she was six months pregnant with their first child. They had another child, but announced their separation in 2006.
Arguably, this couple is the one that people are most rooting for. Glances and body language during their meetings have been analyzed for clues on whether they’d reconnect after 15 years apart. The gorgeous duo (with some enviable hairstyles) started dating in the late ’90s, got married in 2000, and appeared to be the most perfect couple ever until 2005 when they split.
The Motley Crüe frontman and the Dynasty star got married in 1986, and the two made a hot rock ‘n’ roll couple until 1993. It was crushing when he left her for Baywatch star Pamela Anderson.
Back when reality TV was still in its infancy, Nick Lachey and Jessica Simpson starred on Newlyweds, a show that followed the 98 Degrees member and the pop princess fumbling through the early days of marriage. The show made it three seasons from 2002-2005, and their marriage lasted about the same length of time.
Jennifer Lopez always grabs headlines with her dating life, but there was something special about the time from 1999-2001 when she dated Diddy (known as Puff Daddy at the time). They were even together when she wore that infamous plunging Versace dress to the 2001 Grammys.
Watching their relationship unfold was like watching The Notebook in real life. So while the two were only a couple for two years (2005-2007), their very cute romance gave fans hope that art would continue to imitate life.
Technically, this very handsome couple consciously uncoupled? But still, the Coldplay frontman and the Goop founder and actress met in 2002, married in 2003, had two children and were together until their separation (whatever you want to call it) in 2014.
Watching The Crown, its easy to see that this couple was doomed from the start. However, in 1981 when the nursery school teacher became a princess in the most epic wedding, it was like watching a real-life fairytale unfold.
The No Doubt frontwoman and the Bush singer got together and made some beautiful music for a while. The two met in 1995 on tour and dated on and off until they wed in 2002. They had three kids together and separated in 2015.
In the mid-’90s, Ellen DeGeneres made TV history by coming out as gay on her sitcom Ellen. Shortly after that, she met Anne Heche and the two became one of the first mainstream LGBTQ couples. While the two only dated three years, at the time, their relationship was groundbreaking.