Before marrying the 41-year-old Good Charlotte rocker in January 2015, the 47-year-old actress was a magnet for tabloids thanks to her romances with fellow A-listers. Her first famous relationship was with her There's Something About Mary co-star Matt Dillon, whom she dated from 1995 to 1998. In a 2006 interview with Parade, Dillon candidly reflected on their relationship.
"I fell in love [with Cameron Diaz]," Dillon said. "It's a very powerful thing when you feel that way about somebody. Cameron was a muse for me. I hadn't been in any deep emotional relationships."
But he also hinted at staying "too long" in the relationship.
"You roll from relationship to relationship because you're afraid of being alone," he said. "When I was lonely, I'd get into relationships just to alleviate the loneliness. I stayed in some too long. You need something to fill the emptiness. It can be another person, drugs, prestige or whatever. I've tried those things. They don't do the trick."
After her breakup from Dillon, Diaz had a very private relationship with Jared Leto from 1999 to 2003. Following their split, she got into a high-profile romance with Justin Timberlake after the two met when she presented him with the award for Best Burp at the April 2003 Nickelodeon Kids' Choice Awards. Two months later, she joined him on his tour with Christina Aguilera.
Diaz commented on their nine-year age difference in an interview with W magazine in 2004.
"It's not like this is the first time in the history of human relationships that people were drawn to one another because of who they are, not what age they are," she said.
In 2002, Diaz talked about her dating life when asked about starring in multiple rom-coms by The Independent and acknowledged that the films were "unrealistic about love."
"I've heard a lot about The Rules, and about men being from Mars and women from Venus, but I don't subscribe to that sort of thing," she said. "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."
But at the end of the day, Diaz and Timberlake weren't meant to be. They called it quits in January 2007 with a joint statement, noting that they had "continued love and respect for one another." Still, their split wasn't without drama. Shortly after, People reported the two got into a public fight at Prince's Golden Globes after-party that year, after Timberlake was spotted chatting with his now wife, Jessica Biel.
"When I met Jess, it was undeniable how beautiful she is," Timberlake wrote about meeting Biel at a party. "I made some sort of sarcastic comment, really dry. Nobody got it except her. She laughed, and I noticed, all of a sudden, and in the way where you wonder if a person's like you, if they have a very dry, dark sense of humor, too."
"I'm kind of really interested in that girl," he recalled. "There was just something about that girl. Kind of interested in that girl. Goddamn it. I had to psych myself up. I had to remind myself that I was me -- giving myself a pep talk, shadowboxing with myself, rubbing my own shoulders."
"Then the Golden Globes came up, and that's when we planned on seeing each other," he continued. "We were both still seeing other people, keeping ourselves safe from getting hurt, from really putting ourselves out there. It took a bit for both of us to admit to ourselves that we were really, really into each other."
"You know, when you're adults it can happen, when people move on in their lives," Diaz said of working together after their breakup.
Timberlake also told ET, "We still think the world of each other and had a great experience together, and now we have a great experience together in a different way."
And by 2010, Diaz was already part of another super-famous couple when she started dating baseball legend Alex Rodriguez. The two caused an internet frenzy when she was snapped feeding him popcorn at the 2011 Super Bowl.
"Oh gosh, I can't even count how many times I've gotten on a plane for love," she said. "It's not unusual in this business; my lifestyle demands it. I'm always traveling for [whispers] c**k. You've got to go where it is."
Still, she did not acknowledge that she was in a relationship with Rodriguez when asked.
"I've been in relationships since I was 16 years old," she said. "In the past three years I've made a conscious decision not to be in a relationship for as long as I want. I've stayed away from all the traps out there for me to just fall into something that will potentially lead me down the same road. ... I want to have a relationship with myself right now."
Though they never confirmed they were dating, according to multiple reports, the two split in September 2011. Rodriguez did have kind words about her during an April 2012 interview with The Insider.
"I don't like talking about my relationships. But I will tell you about CD: She's probably one of the greatest human beings I've ever met, and just an amazing light," he said.
That month, Diaz reflected on her love life in an interview with InStyle and said she had no regrets.
"I would never have guessed that I would end up dating any of the guys I've dated -- never!" she said of her famous exes. "I would rather have my heart broken a thousand times than never to love at all. I have so much love to give -- I'm not empty of love, I'm full of love."
Meanwhile, Diaz was definitely gaining confidence as she entered her 40s. In an October 2012 interview with Esquire, she said she was more content with herself at 40 than she was in her 20s and 30s.
"I'm so excited. Getting older is the best part of life," she said. "Like, I know more than I've ever known. I have gratitude. I know myself better. I feel more capable than ever. And as far as the physicality of it, I feel better at 40 than I did at 25."
She also said she wasn't looking to get married, though she didn't close the door on it.
"It's hard to say. It just wasn't the thing I was drawn to," Diaz said of tying the knot. "I certainly didn't want it in my 20s. Or my 30s."
In 2014, she again told Esquire, "I like being 41. I love it. So much s**t just falls away. Fear, mostly. It's the best age. That's when a woman knows how to work things, or she doesn't care about that anymore. You just stop being afraid. You don't worry about what men think. You just don't worry that time registers anything awful."
In May 2014, Diaz shocked fans when she began dating Good Charlotte rocker Benji Madden, whom she met through his sister-in-law, Nicole Richie. After just seven months of dating, the two got engaged that December.
"You have to find someone in the same place as you are. Timing is everything," Diaz told Cosmopolitan that month. "If you get into a relationship where you want something the guy doesn't want, it's never gonna work. You're never going to get him to be in that place. No matter how old you are, finding the guy who's in the same place as you are and wants to show up is the only way a relationship works, period."
"Here's the thing: You make the same mistake over and over again until you learn your lesson," she added of her exes. "We girls sometimes do the thing where we pick the same person over and over again -- they look and seem different, but deep down, they're the same. And that's on us."
"It was one of those things where everyone tells you, 'You just know when you know,'" she said. "I was like, 'What does that mean? Oh, I get it. You just know when you know.' Like, you're my husband."
She also said her relationship with Madden made her completely forget her dating past.
"You know, nothing matters now that I have my husband," she said. "Like, I don't even remember any of that. All of that is like, that's the thing, that's how I know he's my husband... No one compares. Everything else just like washes and slips away. You realize like, 'Oh this is like the real thing is. This is what real love is. This is what real commitment and devotion is. This is the person you build your life with.'"
"That was the biggest thing I've done in my 40s, and it opened me up in different ways," she shared. "It's pretty awesome. I didn't think it was something I'd do, and I don't know if I'd have done it if I hadn't met my husband. It was a surprise."
"I never knew what love was until I found you," she wrote. "How did I ever live without your love, your friendship, your brilliant mind, your genius sense of humor, and your enormous, loving, beautiful heart?"
"Thank you for being my best friend, my teacher, my partner in life," she continued. "You inspire me every day with your courage and devotion. Thank you for all the support and encouragement in this book and everything in life. I love you forever and ever."
The feeling was definitely mutual. Madden has publicly gushed about Diaz in a way that her past famous exes haven't. In honor of her 44th birthday in August 2016, Madden Instagrammed a sweet message for his wife.
"Happy Birthday to my beautiful Wife, You're my best friend and I'm so thankful for you, sometimes I just want to tell the world," he wrote. "Generous, Kind, Compassionate, Selfless, Humble, Thoughtful, Patient and Loyal. Just a few of the qualities I would use to describe who you are, consistently, everyday."
"Thanks for being you, I'm a lucky guy," he added. "Here's to many more. I love you @camerondiaz."
Since meeting Madden and getting married, Diaz has taken a step back from her acting career and the spotlight, her last film project being 2014's Annie. In 2018, she declared she was "retired" in an interview with Entertainment Weekly.
"I started [experiencing fame] when I was 22, so 25 years ago -- that's a long time," she later pointed out in an essay for InStyle in August 2019. "The way I look at it is that I've given more than half of my life to the public. I feel it's OK for me to take time for myself now to reorganize and choose how I want to come [back] into the world. If I decide to. I don’t miss performing."
"You know, I think the 40s are the best decade," she added. "You just get to be real with yourself, and you can also make necessary changes because you have the experience of looking back on four decades. Looking at patterns and seeing what things really work. You get to let go of giving a s**t about anything. You're done! Don't care. I really don't. It's such a relief."
"I just want to build better, stronger friendships with the people who are in it with me. Of course, that includes my husband," she wrote. "Getting married to him was the best thing that ever happened to me. My husband's the best. He's the greatest human being, and he's my great partner. Marriage is certainly hard, and it's a lot of work. You need somebody who's willing to do the work with you, because there's no 60-40 in marriage. It's 50-50 period. All the time."
A month later, Madden couldn't contain his joy when it came to his new life, Instagramming, "My Wife and Daughter fill me up with so much gratitude. Everyday, I feel so lucky. Just wanted to say it out loud!!! Much Love & Best Wishes."
In April, Diaz spoke about her new life as a mother for the first time during an Instagram Live with Who What Wear CEO Katherine Power, calling motherhood "the best, best, best part" of her life.
"I love being a mother," she said. "I'm so grateful and so happy and it's the best thing ever and I'm so lucky to do it with Benj and we're having the best time. I'm thrilled. I can't believe it."
She praised Madden as a father, sharing, "He's so good. He's such an amazing father. I'm so lucky he's my baby's father. He's incredible. He puts her down and I go into the kitchen and I pour myself a nice glass of red wine. I start my cooking, I put on my show, whatever it is."
"Forever grateful to my wife for making me a Father, and taking such good care of us everyday," Madden wrote. "Best Mom and Wife and Friend. Whether waking up extra early to take care of everyone (3 humans and a dozen animals) or doing all the research and reading to make sure we try our best to be good parents for our daughter, she’s a force of nature and I’m very grateful."
"These guys who want younger girls? You don't want them -- you know why? Guys who want younger girls, are like, developmentally, they're like, not advanced," she said. "They don't want the challenge of a woman who knows who she is or who she wants, or you know, they have the opportunity to not develop themselves. It's like a regression, emotionally. And they want to stay in this place where they don't have to do the work."
Meanwhile, it certainly appears Diaz and Madden are currently living blissful lives as parents and partners.
"In the last seven months I've entered the best phase of my life: motherhood!" she told Rolling Stone in July. "So it's been all about my home and family. And I am trying to participate in a thoughtful way in the larger and most important conversation that our society is currently engaged in."
"Well, since we have a little one, we are really jamming out to some dope Sesame Street jams," she added. "We got 'Baby Shark' in the mix, and of course Benj has written at least a dozen songs for her. So we are doing serious upbeat and often a cappella jams over here."
"I just decided that I wanted different things out of my life," Diaz explained. "I had gone so hard for so long, working, making films, and it's such a grind. And I didn't make any space for my personal life. And then I decided to stop making movies and really focus on my personal life, my personal relationships with my family, my friends. And then Benji and I met each other and we got married pretty much immediately because we both knew that we both had to do it."
"I think you just build a life when you're in your 20s and 30s, and into your 40s, as you know, it's completely different," she continued. "But here I am in my 40s, I'm completely starting over. I decided at the beginning of my 40s to completely start over after I had a whole life that I did something at a high level."
Diaz said she had "peace" in her soul now that she was finally taking care of herself.
"It is a funny journey that got me here," she shared. "But I think that what I realized is that where I am now, I've just become comfortable with not knowing what is going to happen. I have total faith that things are going to work out."
For more on Diaz and Madden, watch the video below.