Turn of the millennium couples don’t get much hotter than this. Back in 1999, and , both now 52, were two of the world’s biggest sex symbols. Leto was adored by millions of teenagers – and plenty of grown adults — after finding fame as blankly brooding Jordan Catalano in My So-Called Life, while Diaz was a globally popular cover girl following the huge success of era-defining movies like The Mask and There’s Something About Mary. On paper, they were a great match — and for a few years they were in reality too …
How it began
Diaz was 26 and a few months out of a serious two year relationship with actor (he even once described her as his “muse”). Leto, less than a year older, was also single after his own LTR with TV actress . Perfect conditions for a perfect couple to form: Leto apparently slipped his number to Diaz at a Hollywood party after being introduced by mutual friends.
Despite both being certified A-listers, they managed to keep their romance largely under the radar, described by The Telegraph at the time as “Hollywood’s most photogenic, but least photographed couple.” When they were spotted together, though — perhaps chilling out at the beach or browsing at the bookstore — they usually looked deeply in love. They were just way too cool to take it public; despite being at the height of their careers, they never once posed together on the red carpet.
How long it lasted
Even though you might barely remember it, the relationship was a pretty long one — almost four years! The couple moved in together but always denied any of the inevitable rumors about an engagement. “I don’t think it is necessary to walk down the aisle in a white dress to maintain a relationship,” Diaz told The Mirror. “It’s great to have a partner, but I don’t see how a piece of paper means anything at all. I wouldn’t be unfulfilled if I didn’t marry.”
How it ended
The pretty pair split in 2003. No official reason was given.
After the split, it wasn’t long before Diaz moved on with another major heartthrob of the era, , who she dated for four years from 2003, while Leto’s next high-profile relationship was with , who he dated for a few months the following year.
It wasn’t until 2015 that Diaz did decide a piece of paper meant something after all, when, aged 42, she married Good Charlotte’s and went on to have two children with him, daughter Raddix, 4, and baby son Cardinal, who was born in March 2024.
Leto, meanwhile, has remained a bachelor but was in an on/off relationship with model for several years before they finally split for good in 2022.
What they said about each other
The fiercely private couple rarely spoke about each other, or even really acknowledged that they were together, but Diaz did once say, pretty adorably, “I don’t really want to talk about him. Just know that I love him more than anything.” She also described the actor as her “best friend”, adding “The relationship grounds me, makes me feel like I have a home.” Leto, on the other hand, said he “would rather not talk about it.” Very Jordan Catalano.
What they say now
Neither party has talked directly about the other since, but Diaz has spoken openly in interviews about how her marriage to Madden is different from every previous relationship because he treats her as an equal. “Somehow my husband has just been able to kind of show me what it’s like not to have that [inequality] be a part of a relationship,” she said. “I had boyfriends before, and there’s a really, really distinct difference between husbands and boyfriends. I never experienced that before. I’d never been loved in that way.”
Leto, though, just says he’s not very good in relationships because he’s “too obsessed with creative ambitions and goals.” He also told Details magazine that he’s not really the marrying kind. “I don’t really believe in settling down,” he said. “That term implies that the current path I’m on isn’t valid. It’s not always about living your life the way people have lived before you.” Once again … very Jordan Catalano. He really is a method actor.
Key relationship take-outs
It might feel like a distant memory now, but these two were serious about each other, with Diaz even taking a career break at the height of her fame to spend more time with Leto after shooting three movies in a row. “I wanted to spend more time with my loved ones,” she said in 2002. “When you look at your life, you don’t want to take anyone or anything for granted. If you’re just working, working, working, and you’re not getting anything else back, then it’s not fulfilling.”
Ultimately, though, it feels like this relationship was that classic, intoxicating late twenties rite of passage that teaches you how to be a grown-up —but ends up letting you know what you do and don’t want in the future. “I’ve heard a lot about the rules, about men being from Mars and women being from Venus, but I don’t subscribe to that sort of thing,” Diaz told The Independent in 2002, not long before the couple split. “My rule is that there are no tricks in this game. I believe in honesty and communication and in treating people the way you want to be treated. Love should be unconditional.”
