Once upon a time in 1999, a young blonde pop star named Jessica Simpson met another young blond-ish pop star, Nick Lachey, at a Teen People party, and they immediately fell in love. Lachey even wrote a song about their passion — that would be “My Everything” — and then he and his new bride signed up to film their love for an MTV reality show called “Newlyweds.” But instead of finding “happily ever after,” Lachey and Simpson found grounds for divorce in 2005 after three years of marriage.
In 2001, every teenager with access to MTV and Teen People wanted to find the Britney Spears to their Justin Timberlake (or vice versa). With those two ruling pop music, not even their questionable fashion could mar the public’s love for their romance. Sadly, matching denim outfits wasn’t enough to make this last: The couple broke up in 2002, and many listeners believe Timberlake’s “Cry Me a River” is about his relationship with Spears.
Johnny Depp and Winona Ryder had amazing chemistry on- and off-screen, from “Edward Scissorhands” to the tattoo parlor, where Depp had “Winona Forever” inked on his arm. Alas, although we adored their courtship, Depp and Ryder weren’t meant to be.
Madonna’s four-year marriage to Sean Penn was one of the wildest rides of the ’80s, and that’s saying something, but we agree with her words after their divorce in 1989: “I do believe we all have soul mates,” she told People magazine. “I don’t believe that we necessarily end up with them.” After their split, both Madonna and Penn moved on to new relationships (several times).
Lenny Kravitz and former “Cosby Show” star Lisa Bonet seemed tailor-made for each other, right down to their love of hippie style. The pair met at a New Edition concert in 1985 and married in 1987, welcoming daughter Zoe a year later. “We were very young, and it was wonderful,” Kravitz recalled in 2013, 20 years after their marriage came to an end. Now, “Zoe’s mom and I are best friends,” Kravitz said. “It’s interesting because that’s how the relationship started.” Bonet is now married to actor Jason Momoa.
One of our other favorite ’90s couples again includes Depp, who dated model Kate Moss from 1994 to 1998. A pairing with that much heat and great hair should never fall apart.
David Arquette and Courteney Cox were so adorable together, they could be endearing in a horror movie, as they were in 1996’s “Scream.” It was a shock when, after 11 years of marriage, the two announced they were breaking up in 2010. The couple, who have one daughter, Coco, have remained friends.
When “Milkshake” singer Kelis caught Nas’ attention at an afterparty for the 2002 MTV Video Music Awards, the artistic couple quickly became the hottest pairing in hip-hop. Unfortunately, the sparks flying between the two combusted in 2009, when Kelis — seven months pregnant with the couple’s son, Knight — filed for divorce after four years of marriage.
Aaron Carter misses the way things were. The singer tweeted in March 2014 that he’ll spend his life “trying to better myself to get back to” his ex Hilary Duff, calling her “the love of (my) life.” Duff and Carter dated as teens on and off from 2001 to 2003, and just the thought of them reuniting makes us nostalgic.
The reason we’re wistful for the days when Ryan Gosling was dating Rachel McAdams is simple: If the two people who starred in “The Notebook” can’t make it work, who can?