All the Men in Cameron Diaz’s Life: From Keanu to Benji

Although she is now happily married to Good Charlotte’s Benji Madden, Cameron Diaz certainly had her share of Hollywood romances. However, some of these relationships were more serious than others, some were just hookups, and some were just rumors. For example, despite her amazing on-screen chemistry with Ashton Kutcher, the two were never in a relationship – contrary to popular belief.

Cameron Diaz / Benji Madden, Cameron Diaz / Cameron Diaz, Justin Timberlake / Cameron Diaz, Matt Dilon.
Source: Getty Images

The starlet dated actors, directors, and athletes, but she really has a thing for musicians. Diaz has had plenty of high-profile romances with singers like Justin Timberlake, Jared Leto, and her eventual husband, Benji Madden. She was also linked to athletes like Alex Rodriguez and surfer Kelly Slater.

You may have forgotten she dated some of these men, and a few of her brief romances may surprise you. So, without further ado, this is Cameron Diaz’s relationship history.

Benji Madden: 2014-Present

Cameron Diaz began dating Good Charlotte’s Benji Madden in May 2014. They actually met through Nicole Richie, Madden’s sister-in-law. The love birds were engaged for just 17 days before they tied the knot in a Jewish ceremony on January 5, 2015.

Benji Madden and Cameron Diaz attend an event.
Photo by Donato Sardella/Getty Images

In January 2020, the happy couple announced an addition to their family. They welcomed their first bundle of joy, their daughter Raddix Madden. The couple is still together and seems to be happy. Madden even has a tattoo of Cameron’s name on his chest. Now, that’s true love right there.

Elon Musk: Briefly in 2013

Technology entrepreneur, investor, and engineer Elon Reeve Musk − who is also the lead designer of SpaceX, co-founder, CEO, and product architect of Tesla, Inc. − still finds time to date. With his scientific mind and wild simulation theory, he walks the fine line between genius and crazy.

A portrait of Elon Musk.
Photo by Britta Pedersen-Pool/Getty Images

Rumors began to swirl that Musk was dating actress Cameron Diaz back in 2013. The pair met after Diaz bought a car from Tesla Motors, according to The Sun. Apparently, the two kept in touch after the meeting and had a short-lived romance. Musk would fly to Los Angeles frequently to visit her.

Alex Rodriguez: 2010-2011

Cameron Diaz dated Alex Rodriguez, but her romance with the former New York Yankees player was also a brief one. The two were together for just about a year in 2010 and 2011. It was actually one of the starlet’s most high-profile relationships. The two seemed happy together before it suddenly ended.

Alex Rodriguez and Cameron Diaz pose for a picture together.
Photo by George Pimentel/Getty Images

After their breakup, Rodriguez said: “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.”

Adam Levine: Hooked Up in 2010

If you haven’t been living under a rock for the last two decades, you definitely know who Adam Levine is. Whether you like him in Maroon 5 or watch him on The Voice, this guy certainly doesn’t have a problem with the ladies.

Adam Levine attends an event.
Photo by Axelle/Bauer-Griffin/FilmMagic/Getty Images

Well, the singer apparently dated Cameron Diaz back in 2010 when the pair were spotted out together. Other reports claim it was just a hookup. It’s true; just because two people are seen hanging out together, it doesn’t necessarily mean they are dating.

Keanu Reeves: 2009-2010

The beloved Canadian actor Keanu Reeves has become a household name. With all his incredibly successful movies and impressive resume, this guy has become a Hollywood legend. It’s no surprise that the movie star had all the beautiful girls swooning for him, including Cameron Diaz.

A portrait of Diaz and Reeves on a movie set.
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It’s unclear whether the pair were actually dating. They were seen together in 2009, and reports claim the two were very touchy-feely. But that’s pretty much all we know. Since they were never spotted together again, we can assume this was just a hookup.

Paul Sculfor: 2008 to 2009

Cameron Diaz dated British model Paul Sculfor back in 2008. This one was also short-lived, and the pair broke up in 2009. Many photos surfaced of the pair kissing and cuddling. They are clearly okay with a little PDA (public display of affection). Apparently, the only reason they broke up was because of their living situations. Long-distance isn’t easy.

A picture of Diaz and Sculfor standing on a balcony.
Photo by Chris McGrath/Getty Images

Reportedly, the model “dumped” Diaz because the blonde beauty refused to move to the U.K. “Paul and Cam were really into each other, and even marriage wasn’t out of the question,” a source close to the couple said, adding, “But Paul wasn’t getting much modeling work in the States.”

Gerard Butler: Hooked Up in 2008

Gerard James Butler is a talented British actor. The Scotland-born star is also famous in America, known for his roles in The Phantom of the Oprah, 300, and P.S. I Love You in a career that spans decades. He was also rumored to have a brief fling with Diaz in 2008.

Gerard Butler attends an event.
Photo by Amanda Edwards/Getty Images

And when we say fling, we mean they were just hooking up. It was nothing serious, but it was apparently a little more than a one-night stand. Although they were seen together for a little while, they prioritized their busy schedules and called it quits.

Sean “Diddy” Combs: 2008

Rapper Sean Combs, otherwise known as P Diddy, had a romance with Cameron Diaz, according to Us Weekly. The pair started going out in 2008 and broke up in 2012. That’s a pretty long time. Diddy admitted that Diaz was “the one who got away.”

Diaz and Combs arrive at an event.
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During a night out, when people started talking about Diaz and her now-husband Benji Madden, the rapper reportedly said: “If I could turn back time, things would be different!” He then added, “she’s the sexiest girl in the world.”

Bradley Cooper: Late 2007 – Early 2008

Reportedly, back in late 2007 to early 2008, Diaz dated the very attractive actor Bradley Cooper. The Academy Award-winning star has dated plenty of beautiful starlets in his day, and it looks like Cameron Diaz was just another one.

A picture of Bradley Cooper and Diaz during an event.
Photo by Jeff Vespa/WireImage/Getty Images

It probably wasn’t a serious relationship because they never announced it. Again, just because they were seen together doesn’t automatically mean they were dating; maybe they were just buddies. “I think she’s great,” Cooper later told PEOPLE. “We’re good friends.” So, there you have it, folks: just friends.

Kelly Slater: Briefly in 2007

In 2007, rumors and speculation started to surface about Diaz dating pro-surfer Kelly Slater when the two were spotted surfing together in Hawaii. There was also a rumor about the actress flying to Hawaii after her breakup with Justin Timberlake. Apparently, the surfer was helping her get through the difficult time.

A portrait of Kelly Slater by the beach.
Photo by Adam Pretty/Getty Images

However, like many people spotted out together, Slater told PEOPLE that they were “just friends,” even though they were seen having dinner, playing golf, and surfing together. I don’t know about you, but I grab dinner and hang out with my friends all the time. It doesn’t mean we’re dating.

Tyrese Gibson: January 2007 – January 2007

It was clear that it was over between Cameron Diaz and Kelly Slater when she was seen kissing Tyrese Gibson at a pre-Oscars party, thrown by Harvey Weinstein, Tamara Mellon, and Tracey Edmonds. A Gatecrasher spy caught the two stars lip-locking at the L.A. club Xenia: “They made out right in front of me on the dancefloor.”

Tyrese Gibson poses for the press.
Photo by Kevin Mazur/Getty Images

However, Cameron Diaz denied the rumors and claimed that she was not dating him. Considering they were together from January 2007 to January 2007, I’d say the two were not that serious. And people kiss their friends sometimes; it’s called “friends with benefits.”

Jude Law: 2006-2007

Back in 2006 and 2007, rumors surfaced that Cameron Diaz was dating acclaimed English actor Jude Law. Apparently, the pair met on a movie set, and sparks flew instantly. Their sizzling on-screen chemistry continued when cameras stopped rolling.

Diaz and Law pose for the media.
Photo by Jun Sato/WireImage/Getty Images

According to reports, “They had a lot of fun while making The Holiday, and this is the key to their relationship.” Diaz herself kind of confirmed these allegations when she admitted she “fell in love” with the actor after working with him. The passionate romance lasted about a year.

Justin Timberlake: 2003-2006

Back in the early 2000s, Cameron Diaz and Justin Timberlake had a highly publicized romance. According to PopSugar, the pair met at the Nickelodeon Kids’ Choice Awards in 2003 and started dating shortly after. The couple was inseparable! At one point, the actress joined Timberlake on tour. They were together for years.

Diaz kisses Timberlake on stage.
Photo by Chris Polk/FilmMagic/Getty Images

But in 2007, their whirlwind romance came to an end. They both released a statement that said, “We have, in fact, ended our romantic relationship, and have done so mutually and as friends, with continued love and respect for one another.” They worked on two movies together after their breakup: Shrek 3 and Bad Teacher.

Robbie Williams: Briefly in 2003

Cameron Diaz must have a thing for foreign accents because she also dated English singer, songwriter, and entertainer Robbie Williams… allegedly. Reports claim that the pair had a brief fling in 2003. Interestingly, William said that the actress saved his relationship with his now-wife Ayda.

A portrait of Robbie Williams.
Photo by Mark Thompson/Getty Images

On an episode of Robbie and Ayda’s podcast, (Staying) at Home With the Williamses, the musician shared that a conversation with Cameron Diaz is what turned around his relationship with Ayda after a break in their relationship. I guess it’s safe to say that the exes are still friends.

Jared Leto: 1999-2003

Many people may forget that Cameron Diaz and 30 Seconds to Mars singer Jared Leto had a romance. Their relationship lasted quite a while, from 1999 to 2003, according to Us Weekly. There were even engagement rumors flying at one point. But the couple eventually broke up; apparently, Leto wasn’t ready to settle down.

A photo of Jared Leto and Diaz during an event.
Photo by Jeff Kravitz/FilmMagic/Getty Images

After the split, the musician was linked to many other Hollywood starlets, such as Scarlett Johansson, Paris Hilton, Miley Cyrus, and Angelina Jolie. During an interview, Leo explained why he hasn’t been able to commit: “I’m too obsessed with my own creative ambitions and my own goals.”

Edward Norton: Hooked Up in 1999

Acclaimed Hollywood star Edward Harrison Norton is an award-winning actor, successful filmmaker who has made his way around the industry. When he decided to pursue acting, his talent was evident, and he quickly gained recognition. Like many stars, he dated his share of Hollywood ladies.

A picture of Edward Norton and Diaz during a party.
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In February 1999, rumors about Norton and Diaz flew. People reported a lot of PDA from the pair at a Super Bowl party, which only added fuel to the fire. Of course, the fling was done by winter 1999 when the actress started dating Jared Leto.

Matt Dillon: 1995-1998

Back in 1995, Cameron Diaz and Matt Dillon were cast in the same movie together: There’s Something About Mary. The movie, of course, became one of Diaz’s most memorable films, but she also found love on the set. Short-lived love still counts! Although their on-screen chemistry was evident, it didn’t last in real life. The pair split right after they finished filming the movie.

Matt Dillon and Cameron Diaz pose for the press.
Photo by David Giles/PA Images/Getty Images

After the breakup, Dillon told People: “I was dissatisfied with where I was as a man, with my relationships, with my career… I thought my career was who I was. It wasn’t until later that I discovered I was more than that… Cameron was a muse for me.”

Vince Neil: Briefly in 1995

Cameron Diaz also fated a guy named Vince Neil. The name might not ring a bell, but you’ll probably recognize him as the lead singer of a little band called Mötley Crüe. Well, this guy has his own dating history, but one of the starlets he had his arm around was Cameron Diaz.

Diaz and Vince Neil attend an event.
Photo by Ron Galella, Ltd./Ron Galella Collection/Getty Images

The pair began dating in 1995, and they were an unlikely couple, to say the least. This was all the way back in the nineties when these types of relationships made more sense… I think. Although people thought the relationship was random back then, given the fact that the actress has a thing for musicians, it’s not so surprising when you look back now.

Carlos De La Torre: 1990-1994

Before becoming a famous actress, Cameron Diaz had a romance with video producer Carlos De La Torre, whom she met during a commercial shoot. Diaz told People, “I spent the entire day trying to get him to talk to me,” when they first started working together.

A picture of De La Torre and Diaz at a restaurant.
Photo by Ted Soqui/Sygma/Getty Images

The day after the shoot, De La Torre finally decided to give the starlet a call, and the two of them hit it off right away. The two started dating in 1990 and even moved in together. Unfortunately, it wasn’t meant to last forever, and the couple split in 1994.

Who Is Cameron Diaz Married To?

With all her failed relationships in Hollywood, Cameron Diaz finally struck gold when she met her now-husband, Benji Madden, in 2014. The two have become one of the most private couples in Hollywood, trying to keep their personal lives to themselves. Although they chose to fly under the radar, they did give us an inside look into their whirlwind romance.

Josh Madden, Lionel Richie, Nicole Richie, Joel Madden, Cameron Diaz, and Benji Madden attend an event.
Photo by Donato Sardella/Getty Images

From a small wedding ceremony to romantic getaways, the relationship between the actress and the singer is surprisingly beautiful. Their strong bond is undeniable, and with a little bundle of joy thrown into the mix, things keep getting better for this happy couple.

Here’s the scoop on how Cameron Diaz and Benji Madden make their marriage last.

Cameron Diaz Wasn’t Sure About Marriage

Cameron Diaz wasn’t always sure if marriage was for her. She dated a string of Hollywood men and was never in a truly committed relationship. However, it seems like the actress just hadn’t found the right guy to settle down with… until she met Benji Madden, that is.

Cameron Diaz Visits “The Tonight Show Starring Jimmy Fallon.”
Photo by Theo Wargo/Getty Images

During a 2016 interview with Harper’s Bazaar, a little over a year after walking down the aisle, Diaz shared her thoughts on marriage: “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.”

They Were Introduced by Nicole Richie

Remember when Paris Hilton was dating Benji Madden, and Nicole Richie was dating his brother Joel? Well, as it turned out, Paris and Benji didn’t work out. But Nicole Richie still wanted to set up her man’s twin… and she clearly had Hollywood friends.

Richie and Diaz walk the street together.
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Richie and Diaz were great friends, and she thought they would get along great, so she connected them. “I’m going to take responsibility for everything!’” Richie confessed in an interview with Watch What Happens Live. “I approve of anything that’s going to make Benji happy.”

Love at First Sight

Love at first sight is one of those phrases that only happens in movies – not in real life. When you think you might have found love at first sight, it usually ends in heartbreak if you’re not in a rom-com. But some lucky people get that fairy tale kind of love.

A picture of Diaz and Madden on a night out.
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Cameron Diaz and Benji Madden are one of those lucky couples. As soon as they saw each other, there were sparks in the air. The actress told Andy Cohen, “The first thing I said when I first met my husband was ‘he’s hot.’” That’s definitely a great first impression.

How Long Have They Been Together?

Cameron Diaz and Benji Madden are known for their privacy. They like to keep their relationship and personal life private, so many fans aren’t even really sure exactly how long these two have been together. How long were they dating before tying the knot?

Cameron Diaz attends an event.
Photo by JB Lacroix/WireImage/Getty Images

In 2014, news broke about the pair, and the couple confirmed their relationship and made it public. This means they have been together for almost eight years! Cameron Diaz has stepped out of the spotlight since then, so she really seems to have shifted her focus to her family life.

An Intimate Wedding

Every girl imagines her wedding day, but when if you’re an A-lister, you can make those wedding dreams come true. Many celebrities dream of a fancy Kim Kardashian wedding, with the most beautiful flowers, stunning dresses, and rich and famous guests bringing you the most wonderful wedding gifts.

Madden and Diaz take a picture at home.
Source: Instagram /@benjaminmadden

But not this Hollywood couple. According to Us Magazine, Diaz and Madden exchanged vows in the actress’s Beverly Hills home. “We got married in our living room in front of friends,” Diaz revealed to Andy Cohen. It was an intimate ceremony, but some big names close to the couple were there, including Drew Barrymore and Gwyneth Paltrow.

A Quick Ceremony

The quiet and intimate wedding also didn’t last until the early hours of the morning. We’ve seen brides turn into monsters trying to make sure everything is perfect for their big magical day, but Diaz was the furthest thing from a bridezilla. The party meant nothing to her; in fact, she didn’t really have one.

A picture of Benjamin Madden on their wedding day.
Source: Instagram /@benjaminmadden

Only 96 people showed up for the low-key nuptials, and instead of a long party, the short ceremony was over 15 minutes. Diaz had Drew Barrymore and Nicole Richie as her bridesmaids, and that’s all that mattered. She later described the wedding as a “beautiful” and “heartfelt” few minutes.

Marriage Isn’t Always Easy

No matter how much love and passion two people have, relationships are never as picture-perfect as they may seem. Every family has its share of issues and solving them together is key! Cameron Diaz acknowledged that marriage can be difficult during an honest and authentic interview with Ellen DeGeneres.

A picture of Madden and Diaz on a cold and windy day.
Source: Instagram /@benjaminmadden

She explained that being a wife has forced her to understand specific things about herself that may be difficult to accept: “I learned all these things about myself I wish I never learned about myself, and I wouldn’t have known them if I didn’t get married.”

Privacy Is Important to Them

If there is one thing that Cameron Diaz and Benji Madden cherish, it’s their privacy. Ever since they got together, Diaz has stepped out of the spotlight, and Good Charlotte also took a little break from mainstream music. They decided there were more important things than fame.

Cameron Diaz tries to cover her face from the media.
Photo by Robert Kamau/GC Image/Getty Images

The pair keep the intricate details of their marriage hidden from the media as a personal choice to protect their family. “The less outside elements or influence that there is, the better for anyone,” Madden revealed. “That’s our vibe.”

Opposites Attract

You know what they say, opposites attract! It’s no secret that people tend to be attracted to people different than them. Sure, it’s important to have shared interests, but different personalities can really make for a beautiful relationship.

Benji Madden performs on stage / A photo of Cameron Diaz surfing.
Photo by Corey Perrine, Getty Images / Frazer Harrison, Getty Images

Cameron Diaz and Benji Madden couldn’t be more different, but that’s what brings balance to their marriage. The starlet explained that being different is the reason they complement each other so wonderfully: “We are both just weird enough for each other.”

What Is Cameron Diaz Doing Now?

As we mentioned, Diaz has stepped out of the spotlight. The movie starlet used to take over our screens, but it seemed like she suddenly disappeared. We haven’t seen her since she portrayed Miss Hannigan in the 2014 version of Annie.

Diaz poses for the press.
Photo by Karwai Tang/WireImage/Getty Images

The actress hasn’t made any on-screen appearances since, and she is in no rush to get back to acting. Instead, she has turned her focus to her health and the wellness industry. Whenever she has spare time, she prefers to spend it with her husband, not a movie set. She certainly has her priorities in check!

Celebrating Their Love

A couple celebrates their anniversary in order to mark another year together. It’s an important day to signify what should have been the greatest day in your life and your undying love for your significant other. Needless to say, some people take their anniversary more seriously than others.

An elevated view over Florence, Italy.
Photo by Gary Yeowell/Getty Images

Cameron Diaz and Benji Madden definitely make sure to honor their relationship and commitment to each other properly every year. They always do something to celebrate. In 2018, the couple spent their anniversary in Italy, where they traveled around the romantic city of Florence and shared a nice quiet dinner.

They Have an Equal Relationship

One of the things that can destroy a relationship is a power complex. Control should never be part of a relationship, and there should always be a feeling of mutual love and respect. That’s one of the reasons Cameron Diaz is happy in her marriage.

Diaz attends an event.
Photo by Kevin Mazur/WireImage/Getty Images

Diaz explained that when it comes to Benji, she feels like his equal, not an object – the way many women are often made to feel. “My husband has been able to show me what it’s like to … be an equal,” she said. “And I’ve learned so much from him. I look at him every day, and he inspires me.”

Diaz Is Close With Benji’s Family

It’s not uncommon for married women to not get along with their in-laws. You know how some moms can get. They have that mentality of “no one is good enough for my perfect son,” which kind of makes everything awkward. But if you do get along with your in-laws, it will make your life much easier.

A picture of Joel, Cameron and Benji Madden.
Photo by KMazur/WireImage/Getty Images

Luckily for Diaz, she has a wonderful relationship with Madden’s entire family. This includes her sister-in-law Nicole Richie and her father, Lionel Richie. Diaz and Nicole are often spotted hanging out or going shopping together.

They Are Not Afraid of a Little PDA

Many couples try not to show their affection in public, especially celebrities. They know it’s going to spark rumors and become headline news. Although they do enjoy their privacy, Diaz and Madden don’t shy away from PDA.

Benji Madden and Cameron Diaz attend a basketball game.
Photo by Noel Vasquez/GC Images/Getty Images

The two have been seen kissing. They have also been photographed at an Italian restaurant in Los Angeles where they enjoyed a romantic date, and according to E! News, they “looked more in love than ever!” They love each other and don’t see a reason to hide it. I mean, they are already married. It’s not like they have to worry about dating rumors.

Brings Out The Best in Her

Marriage is a double-edged sword. It can bring out the best in you, or it can bring out the worst in you. When it comes to Diaz, marriage certainly brought out the best in her. A source revealed to PEOPLE that the actress feels “very fulfilled” since she created a life with Madden.

A picture of Madden and Diaz at the airport.
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However, we don’t have to rely on these sources. Diaz herself is never shy about discussing the positive impact that getting married had on her life. It’s the most important thing to her, and she says so in interviews all the time.

Cameron Diaz Feels Complete

With all the happiness and positivity that being a wife has brought to her, Diaz feels like her life is now more complete. Before getting married, she thought she knew what she wanted, and she was content. Meeting Benji and getting married challenged all that… but in the best way possible.

A screengrab of Cameron Diaz’s video at home.
Photo by World of Wonder/Getty Images

“She has become a new person with more self-confidence and grounding,” another source revealed. “Cameron needed something different in her life, more substance and a relationship where she felt loved.” We’re very happy for her!

Diaz May Have Helped Gwyneth Paltrow With Her Undercover Wedding

As we know, Diaz has a very intimate wedding ceremony. PEOPLE reported that she may have used her own private wedding as inspiration to help her celebrity friend Gwyneth Paltrow plan her nuptials to Brad Falchuk.

Paltrow and Diaz pose for a picture together.
Photo by Dave M. Benett/Getty Images

Although the media knew that Cameron Diaz and Benji Madden were going to get married, the actress still managed to keep their ceremony private. The source speaking to PEOPLE said that she passed her planning strategies to Gwyneth Paltrow. You have to be very sneaky when you want a low-key wedding in Hollywood.

Benji Madden Feels Grateful for His Wife

Cameron Diaz isn’t the only one to gush about her spouse. Madden is well-aware of how blessed he is to be married to the actress and wouldn’t trade her for the world. Once in a while, he even shows his love on social media.

Benji Madden smiles as he poses for the press.
Photo by Axelle/Bauer-Griffin/FilmMagic/Getty Images

On Diaz’s 45th birthday, Madden took to Instagram to pay tribute to his wife and admitted how lucky he is to have her: “I feel like I am the luckiest guy alive,” he wrote in the caption. “You got me till the end, baby!” Aww.

They Found “The One”

Not everyone believes in soulmates. It’s like a fairy tale we dream of as kids, but most of us grow up and realize it’s just a fantasy. However, some very few lucky people believe in this fairy tale type romance after meeting their soul mate.

Benji Madden and Cameron Diaz attend a basketball game.
Photo by Noel Vasquez/GC Images/Getty Images

Diaz and Madden were no different. They didn’t believe in soulmates until they met each other. During her interview with Andy Cohen, the actress revealed that her connection with Madden is “the real thing,” and he’s the only person she can see herself building a life with. “That’s how I know he’s my husband… no one compares.”

Expanding Their Family

In 2019, the rumor mill claimed that Diaz and Madden were expecting twin girls, but as far as we know, there was no truth to the tabloid reports. Apparently, the couple wasn’t planning on becoming parents. In 2014, when she first started dating Madden, Diaz told PEOPLE that she was never really “drawn to” being a mom.

A photo of Cameron Diaz during a press conference.
Photo by Tommaso Boddi/Getty Images

However, it turned out that kids actually were in their future. As we mentioned, both of their mindsets changed a lot since tying the knot. By December of 2019, the couple welcomed their first child, Raddix Madden.