11 Celebs Who Married Their Best Friend (12 Whose Relationship Made Them Enemies)

Hollywood isn’t just about big blockbuster films, groundbreaking TV series, and critically acclaimed performances. It’s also about the relationships, marriages, and divorces. Famous Hollywood couples draw in a great deal of attention and are always in the headlines. Fans and the media care deeply about celeb couples and everything that goes on between them. From the dating phase to starting a family, a famous couple is under the intense media spotlight. There is always a great deal of pressure on the couple. The paparazzi follows them around, the media can’t stop reporting on them and fans have high expectations of a fairytale love story.

There have been a plethora of famous Hollywood couples. They fall in love on a grand stage with the world watching. Some famous couples are lucky enough to have fallen in love with their best friend. These couples became friends first before they took their relationship to the next level. These couples are still together and growing stronger. However, that isn’t the case with every couple. Some famous couples seemed like they’d last forever. Instead, the relationship falls to pieces and they went from lovers to bitter enemies. Here is a look at 11 Celebs Who Married Their Best Friend (12 Whose Relationship Made Them Enemies).

23 Rob Kardashian & Blac Chyna (Enemies)


Rob Kardashian has been in several high profile relationships. In most cases, they ended on bad terms and Rob took to social media to vent. However, one break up, in particular, left him bitter and furious even a year after it was over. Rob is a member of the famous Kardashian-Jenner family and appeared in the popular reality series Keeping Up with the Kardashians. Rob was in a highly publicized and toxic relationship with model Blac Chyna.

The relationship was complicated from the start since at the time Chyna’s ex Tyga was dating Rob’s half-sister Kylie Jenner. Eventually, the family and Chyna put their differences aside and the couple seemed happy. After three months of dating they became engaged. Their daughter Dream was born in November 2016. Not too long after, Rob and Chyna announced they decided to split up. Rob apparently took the break up hard and things seemed to get worse. A year later in 2017, Rob posted a series of explicit pics of Chyna and accused her of straying from him when they were together. He has since deleted the pics and his bitter rant. Chyna said, “I was devastated, of course. I’m like, ‘How could somebody, like, post these pictures of me?’ This is a person that I trusted. I just felt betrayed.” In late 2017, the drama continued as Rob sued Chyna for assault.  (People)

22 Carey Mulligan & Marcus Mumford (Best Friends)


Some famous celeb couples are friends for a few years before dating. However, none of these couples can hold a candle to the friendship between Carey Mulligan and Marcus Mumford. Mulligan and Mumford have known each other since they were kids. Mulligan found a great deal of success as a singer and actress. She has appeared in several films, such as, Drive, Shame and The Great Gatsby. Mumford is best known as the lead singer for the band Mumford & Sons. They have released several popular albums and singles that reach the top of the charts.

Mulligan and Mumford had been friends during their childhood after meeting at Church camp. They became pen pals and wrote back and forth. However, they lost touch with each other as the grew older. They reconnected as adults after both found a great deal of fame and success. They first became friends but soon started dating. They worked together on the 2013 Coen Brothers film Inside Llewyn Davis. They married shortly after completing work on the film. They dated for a few months before getting married in April 2012. The relationship continues to get stronger and stronger. The relationship is so successful because of the strong friendship. They have two children together.

21 Madonna & Guy Richie (Enemies)


Madonna is one of the best selling solo artists of all time. She toured the world and dominated the Billboard charts. She was dubbed the “Queen of Pop” and was constantly making headlines throughout the 80’s and 90’s. She's one of the most controversial Hollywood stars of all time. In 1998, she began to date director Guy Ritchie. Two years later, they married at Skibo Castle in Scotland. They have one son together, Rocco Ritchie, and adopted a Malawian boy, David.

In 2008, Madonna filed for divorce citing irreconcilable differences. The divorce was finalized by the end of the year but that was only the beginning of their court battles. The two Hollywood celebs have often been on bad terms with each other. In late 2015, Rocco joined his mother on her tour but abruptly left after they had a falling out. Instead of returning to the U.S. he stayed with his father in London. Madonna and Ritchie were locked in a brutal nine-month trial for custody of Rocco. The judge ruled in Ritchie’s favor and decided that Rocco will be based out of London. Madonna was unhappy with the ruling and took to social media to voice her displeasure. Madonna and Rocco have since reconciled.

20 Mila Kunis & Ashton Kutcher (Best Friends)


Mila Kunis and Ashton Kutcher both had their first big breakthroughs in the popular sitcom That 70’s Show, which aired from 1998 to 2006. In fact, they played on-again, off-again love interests Jackie Burkhart and Michael Kelso. However, they were only friends off camera. After the series, they both went their separate ways and in were high profile relationships.

In 2012, both stars were single and had stayed in touch over the years. Mila said, “When we first ran into each other, we'd always kept in touch on like AIM…so we always kept in touch since after '70s. We'd pop up on each other's thing and be like ‘Hey, oh my god! How are you? How's life?’ ‘Like everything's good!’ ‘Great!’ [I wasn't thinking about him romantically], no, not at all!” (EliteDaily) However, they reconnected when Ashton attempted to set up Mila with his friend. Ashton and Mila started a causal relationship with the intention to date other people. Ashton said, “It was funny because I’d just done this movie called No Strings Attached and she just did a movie called Friends With Benefits and we legitimately lived out our movies, which was virtually the same movie.” (DailyMailUK) They soon realized they wanted to be more than just friends with benefits and the relationship blossomed. They married in 2015 and have two children together.

19 Ariana Grande & Jai Brooks (Enemies)


Ariana Grande is one of the most famous pop stars in the world. She sold millions of records, tours all over the world and often tops the music charts. Her personal life and relationships are of great interest to her fans and the media. In 2012, Grande was on the verge of superstardom when she began a long distance relationship with Australian Youtuber Jai Brooks. However, they broke up in 2013 and Brooks unleashed on his ex. He took to social media to rant about Grande allegedly being with Nathan Sykes. Brooks wrote on Twitter, “Yes, it does suck. Yes, I was left for another man.” (HollywoodLife)

Despite the long rant, Grande and Brooks actually got back together not long after. However, the couple still had their problems. In 2014, Grande was by her dying grandfather’s bedside but Brooks was nowhere to be seen. Grande was hurt by the fact that he wasn’t there for her. After her grandfather’s passing she wrote, “I thank my loves for being so in tune to what is good and right for me and my heart. I hope you will surround yourselves with people who will be there for you thru the bad times, not just the good.” (DailyMailUK) Not long after, Grande ended the relationship permanently.

18 Jessica Alba & Cash Warren (Best Friends)


Jessica Alba is widely considered one of the most beautiful celebs of all time. She often ranks very high on every hottest and most beautiful list. Many men around the world dream of marrying her but only one guy got to. Alba is best known for her role on the TV series Dark Angel. She has gone on to have a very successful film career. In 2005, Alba starred in the superhero film Fantastic Four and later in its sequel, Fantastic Four: Rise of the Silver Surfer. In 2004, Alba met the son of actor Michael Warren, Cash Warren, while filming Fantastic Four.

They started out as friends briefly before it went to the next level. According to OK Magazine, “Jessica said they had a ‘very, very, very short’ time as friends before they got together romantically and tied the knot in 2008.” They married in May of 2008 and now have three children together. The relationship grows stronger each day. Despite being friends for a brief time there were always feelings between them. Alba said, “I just knew when I met him that I was going to know him forever. It was weird. He instantly felt like family.” She added, “I'd never felt like that with anyone. We got each other. We're kindred spirits.” (OKMagazine)

17 Justin Timberlake & Britney Spears (Enemies)

Justin Timberlake and Britney Spears are two of the most recognizable stars in the world. At one point, these two megastars crossed paths well before either achieved any level of fame. In their younger days, both were cast members of the Disney Channel series The Mickey Mouse Club. Later, Timberlake gained worldwide fame as a member of NSync and Spears became the “Princess of Pop.”

In 1999, they had everyone buzzing when they started dating. However, the teen sensations suddenly broke up in March 2002. The break up was apparently hard on Timberlake and he felt the need to address it in a song. He made headlines when he released the single “Cry Me a River.” The single was viewed as addressing the relationship and taking a subtle dig at Spears. In the song, he implied that Spears had been unfaithful. The video confirmed it was about Spears because it featured a Britney Spears look-a-like. According to Spears, Timberlake informed her ahead of time about the video and she could have stopped it. She said, “I think it looks like such a desperate attempt, personally. But that was a great way to sell the record. He's smart. Smart guy.” (RollingStone)

16 Lea Michele & Corey Monteith (Best Friends)


Lea Michele and Corey Monteith first became friends before falling in love with each other. They remained a couple until Monteith’s sudden passing. Lea Michele and Corey Monteith became household names after starring in the popular Fox musical comedy Glee. They portrayed love interests Rachel Berry and Finn Hudson. They first became friends while working on the series. At the time, Michele was in a heavy relationship with Theo Stockman. Rumors began to circulate that Michele and Monteith were more than just friends.

In 2012, they went public with their relationship. Their friendship grew into a real love story. Michele said, “I don't even remember a time when he wasn't my boyfriend. No one knows me better than Cory. No one knows what it's been like to go through this more than he does. Feeling like you have that net underneath you allows you to jump higher and go farther. He makes me feel like I can do anything.” She added,“For the first time in my life, I feel really, really settled and happy. I feel like the luckiest girl in the world.” (MarieClaire) Sadly, Monteith tragically passed away in 2013. Michele was devastated by his sudden death, as were his many fans.

15 Naya Rivera & Big Sean (Enemies)


Most Hollywood couples break up on bad terms and in grand fashion. However, a bad break up means months of trash talking. Naya Rivera had her big breakthrough with her role as Santana Lopez on the popular Fox musical Glee. Rapper Big Sean has released several popular albums, such as, Finally Famous, Hall of Fame and I Decided. They started dating in April 2013 and were engaged by October that year. In September 2013, Rivera dropped the single “Sorry” which featured Big Sean.

However, the relationship ended as quickly as it started. In April 2014, Rivera and Sean ended their relationship and engagement. However, soon the real story behind the break up became public knowledge. Rivera claims she caught Sean hanging out with Ariana Grande. Adding insult to injury, she found out about the end of the relationship on social media. In her autobiography Sorry Not Sorry: Dreams, Mistakes and Growing Up, Rivera details fighting with Sean for days and then coming to his home. She said, “I've got a key to your house. I walk in, go downstairs, and guess what little girl is sitting cross-legged on the couch listening to music? It rhymes with ‘Smariana Schmande.’” Rivera added, “I learned that I was no longer getting married from the Internet, and at the same time as the rest of the world.” (DailyMailUK)

14 Will Smith & Jada Pinkett-Smith (Best Friends)


Will Smith and Jada Pinkett-Smith are one of the most recognizable couples in the world. There isn’t a person in the world that doesn’t know that world famous Smith family. Will is one of Hollywood’s most bankable movie stars and Jada had her own fair share of success. Will first gained widespread fame with his starring role in the hit NBC sitcom The Fresh Prince of Bel-Air. Will and Jada first met on the set of Fresh Prince in 1994. She auditioned for the role of Will’s girlfriend but didn’t get the part as it went to Nia Long instead.

However, there was chemistry between Will and Jada but it didn’t evolve into a relationship right away. In fact, they first became close friends in the following months. Jada said, “I met him when I was 19 at an audition for The Fresh Prince of Bel-Air. After we had known each other for many years, we went out for dinner one night [with mutual friends] and I saw that he had grown from this lanky kid to this really responsible man. We started courting each other and our friendship turned into romance.” (GlamourUK) They eventually started dating and married in 1997. They have two children together, Jaden and Willow, who have both followed in their famous parents' footsteps.

13 Sofia Vergara & Nick Loeb (Enemies)


Sofia Vergara is best known for her role in the hit ABC sitcom Modern Family. She has been nominated for several awards for her role in the series. In 2012, Vergara became engaged to her then-boyfriend Nick Loeb. During that time, they had three embryos frozen. The agreement was that nothing could be done with the embryos without the consent of both.

In 2014, Vergara called off the engagement with Loeb. Later in 2014, she began dating Joe Manganiello and they married in 2015. Vergara and Loeb were then locked in a battle over the embryos. Loeb attempted to sue Vergara but later dropped that lawsuit. The next day, the embryos filed a lawsuit against Vergara. According to E! News, “The fertilized eggs were listed as plaintiffs "Emma" and "Isabella" in the suit, and it was requested that Loeb receive custody of the embryos in order for them to live and ultimately inherit a trust fund that was created in their names. The documents stated that Vergara has ‘effectively abandoned and chronically neglected’ the embryos by ‘refusing to consent to their development or care.’” (E!News) The judge ruled in Vergara’s favor and the lawsuit was dismissed.

12 Gwen Stefani & Blake Shelton (Best Friends)


Gwen Stefani and Blake Shelton have wildly successful careers. They were both major stars long before they started dating. Stefani first rose to fame as a member of No Doubt before embarking on a successful solo career. Shelton is one of country music’s biggest stars. In 2011, Shelton became a judge on the then brand new reality competition series The Voice. He’s appeared as a judge in every season of the series. Stefani became a judge for the seventh season replacing Christina Aguilera.

At the time both Stefani and Shelton were married to other individuals. However, they became good friends while working together on the series. At the same time, they were both going through very public divorces. It was a tough time for the both of them but they supported each other as friends. Soon the relationship started to blossom and rumors swirled that they were becoming more than just friends. They continued to deny there was anything going on but in reality, the friendship was going to a whole new level. In November 2015, they finally went public and confirmed they were dating. A rep for Stefani said, “Gwen and Blake are long-time friends who have very recently started dating.” (ET) The couple’s relationship is built on a strong foundation of friendship.

11 Russell Brand & Katy Perry (Enemies)


Russell Brand and Katy Perry were once in a high profile relationship that garnered a great deal of media attention. The pop idol and comedian started dating in 2009 and quickly became engaged. They married in 2010 in India but the relationship soon started to have problems. A year after getting married, Brand filed for divorce citing irreconcilable differences. However, Brand stirred up some controversy when he ended the marriage by text message. They claimed that the relationship was strained because of their intensely busy schedules.

Brand has had some unkind words for his ex-wife. In the documentary Brand: A Second Coming, he openly discussed the relationship. He said, “I'm associated with the very thing I detest: vapid, vacuous, plastic, constructed, mindless celebrity. That's the very sea we're swimming in, ‘Oh, who's he?’ ... ‘He's married to Katy Perry.’” (DailyMailUK)  He also noted that he didn’t like being with one person and would think of other women when being intimate with Perry. Perry hasn’t made any harsh comments like Brand but did speak on the end of the marriage. She said, “He didn't like the atmosphere of me being the boss on tour. So that was really hurtful, and it was very controlling, which was upsetting.” (USMagazine)

10 Sarah Michelle Gellar & Freddie Prinze Jr. (Best Friends)


Sarah Michelle Gellar and Freddie Prinze Jr. are one of the most adorable couples in Hollywood. They’ve been together for almost 20 years and the relationship keeps getting stronger. Part of the reason is the relationship is built on a strong foundation of friendship. They first met in 1997 while shooting the popular horror film I Know What You Did Last Summer. They became close friends while shooting the film and remained friends for several years.

However, that friendship soon turned into much more and they eventually became a couple. It wasn’t until 2000 that they officially started to date. They married on September 1, 2002, in Mexico and now have two children together. However, they both realize how important it was they were friends first. Prinze said, “We were just friends. That's one of the reasons I think our relationship has always been so good. We were just friends for a good two years before we ever went on a date. She knew what kind of guy I was. She knew what my morals were, what my priorities were and vice versa. We already kind of knew all the faults in the other person." (E!News) The relationship gets stronger and stronger each day.

9 Mel Gibson & Oksana Grigorieva (Enemies)


Some relationships end in such an epic fashion that it’s easy to forget the relationship existed. Mel Gibson has starred in blockbuster films and directed epic movies. However, he was once in a relationship that had an ending more epic than any of his films. In 2006, Gibson and his first wife Robyn announced their intention to separate. In 2007, Gibson was linked to Russian pianist Oksana Grigorieva. In 2009, Robyn filed for divorce and pictures of Gibson with Grigorieva began to circulate. Gibson’s divorce was finalized in 2011 but that was only the beginning for Mel. In 2009, Gibson and Grigorieva had their only child together, Lucia.

In 2010, news broke that Gibson and Grigorieva were breaking up. Later in the year Grigorieva filed for a restraining order against Gibson to keep him away from her and their daughter. Gibson filed a counter restraining order against Grigorieva. The following month, recordings of Gibson making slurs, physical threats and offensive comments were leaked online. According to People, “The Jan. 6, 2010 incident led to a domestic violence investigation against Gibson, dueling restraining orders and the continuation of their custody dispute over the course of the summer. But the most shocking twist occurred that July, when an audiotape in which Gibson can be heard unleashing a profanity-laced tirade against Grigorieva hit the Internet.” (People)

8 Jay Z & Beyoncé (Best Friends)

Jay Z and Beyoncé are one of the most powerful and influential Hollywood couples. They’ve both been a dominant force in the music industry for decades. Individually, they’ve released chart-topping albums and singles that broke records. However, news of their relationship trumps anything either star has ever done. There has always been a great deal of media attention around the couple. However, they’ve always been very secretive and keep a low profile when it comes to their personal life and family.

They have been vague about the relationship and how they first met. However, Beyoncé revealed that they were friends for about a year before they started dating. She said, “I was 18 when we first met, 19 when we first started dating.” That would indicate they met around 1999 or 2000. In 2001, both were featured on the cover of Vanity Fair with a whole host of other stars. Ten years after the shoot Jay Z said, “We were just beginning to try to date each other.” (VanityFair) They started dating in 2002 after collaborating on the single “03 Bonnie & Clyde.” They married in 2008 in a private ceremony and now have two children together. They’ve had their problems over the years but have worked through them.

7 Zayn Malik & Perrie Edwards (Enemies)


It’s safe to assume that if anyone ever ends a relationship by a text they should brace for the fallout. Zayn Malik had to learn that the hard way. Malik first rose to fame as a member of the boy band One Direction. In early 2012, Malik began dating Perrie Edwards who is best known as a member of the girl group Little Mix. They became engaged in 2013 but Malik broke if off in 2015. A few months later he began dating supermodel Gigi Hadid.

Malik made headlines when news broke that he ended the four-year relationship and engagement by sending a text message. Not only that but he sent the message while Edwards was out partying with friends. According to the Daily Mail, “Perrie was celebrating Black Magic's success with Jesy Nelson, Jade Thirlwall and Leigh-Anne Pinnock when Zayn's shock text reportedly came through. A source told The Sun newspaper: ‘This was meant to be Perrie's big night, but it turned into a disaster. Zayn's timing could not have been worse.’” (DailyMailUK) Later, Malik retweeted a poll that asked which single is better between Fifth Harmony’s “Worth It” and Little Mix’s “Black Magic”. This was viewed as a subtle jab at Edwards and resulted in #ZaynHasNoChill trending. The break up was tough on Edwards who had some critical words for Malik in the song “Shout Out To My Ex.”

6 Blake Lively & Ryan Reynolds (Best Friends)

Blake Lively & Ryan Reynolds are regarded as one of the most beautiful couples in Hollywood. Lively is best known for her role in the popular drama Gossip Girl. Reynolds starred in several popular films and currently portrays Deadpool in the Deadpool franchise. Reynolds and Lively met in 2010 on the set of the film Green Lantern. It was released on June 17, 2011, to negative reviews and feedback. The film was a major disappointment to audiences and Reynolds. However, one good thing did happen because of the movie. Lively and Reynolds became close friends during filming.

They remained friends once filming was complete. Reynolds said, “We were buddies then. I remember it was funny because for about a year after Green Lantern had come and gone and all that stuff, we were both single.” Their relationship is like a romantic comedy come to life. They realized they had feelings for each other while on a double date. Reynolds added, “We went on a double date. She was on a date with another guy, and I was on a date with another girl. That was the most awkward date probably because we were just like fireworks coming across.” (EliteDaily) They married in 2012 after dating for a year and now have two children together.

5 Taylor Swift & John Mayer (Enemies)


Taylor Swift is known for taking heartbreak and turning into a hit single. She has written about many ex-boyfriends and relationships that didn't work out. Taylor Swift is one of the best selling female artists of all time. She has won numerous Grammy Awards and released several chart-topping albums, such as Speak Now, Red and 1989. John Mayer has also released several popular albums and won a Grammy Award for “Your Body Is A Wonderland”. Both Mayer and Swift are known for dating a long list of Hollywood stars.

Swift and Mayer dated from December 2009 to February 2010. Swift was only 19 at the time that she was dating the much older Mayer. They were only together for a short time but the bitterness lasts much longer. They broke up by the end of 2010 and not on good terms. Swift released a song discussing the breakup, “Dear John”. It included the lyrics, “Don't you think nineteen's too young to be played by your dark, twisted games, When I loved you so.” Mayer responded. “I was really caught off-guard, and it really humiliated me at a time when I'd already been dressed down. I mean, how would you feel if, at the lowest you've ever been, someone kicked you even lower?” (RollingStone)

4 Prince William & Kate Middleton (Best Friends)


Prince William & Catherine, Duchess of Cambridge truly do have a fairy tale love story complete with a grand and spectacular wedding. Not only that but William and Kate will likely one day be the King and Queen of England. Their relationship has always garnered a massive amount of media attention. Speculation ran rampant for months that they were dating and they made major headlines when they got engaged. Their wedding was broadcast all over the world and the birth of their children was front-page news.

Their love story has been told numerous times but some might forget that they actually started off as friends. According to royal biographer Katie Nicholl, William, and Kate first met before they attended St. Andrews University. Nicholl said, “This was really fascinating for me. I was speaking to some of her friends at Marlborough School, which was where she went before St. Andrews, and they said, ‘Uh uh, she didn't meet him at St. Andrews. She met him before she got there…through some of her friends. They knew Prince William and Prince Harry.’” (USMagaizne) In 2001, they reconnected at St. Andrews and became close friends. In fact, they were roommates while at school. The friendship soon blossomed into a relationship. They married in 2011 and have three kids together.

3 Kanye West & Amber Rose (Enemies)

Rose blames Kardashian for the end of her relationship with West. Rose said in 2012, “(Kim’s) one of the main reasons why me and Kanye are not together. She’s a homewrecker!” West stayed quiet on the subject until he responded a few years later. In 2015, West said, “If Kim had dated me what I first wanted to be with her, there wouldn’t be an Amber Rose. It’s very hard for a woman to wanna be with someone that’s with Amber Rose. I had to take 30 showers before I got with Kim.” (Complex)

2 Kim Kardashian & Kanye West (Best Friends)

Individually, Kim Kardashian and Kanye West are two of the most controversial celebs. However, when they got married and combined their powers they became one of the most controversial celeb couples of all time. Reality star Kim Kardashian and rapper Kanye West are always making headlines. They’ve both been in highly publicized relationships that dominated the news for months. However, their relationship has managed to garner even more attention and headlines.

Kim and Kanye have been friends for years long before they started dating. In 2012, fans and the media were buzzing when Kim and Kanye revealed they were an item. They married in October 2013 on Kim’s birthday. They have three children together and are one of the most influential couples in Hollywood. They started off as friends for years before dating. In fact, Kanye even referenced being Kim’s friend and having feelings for her on the track “Theraful”. The lyrics included, “And I'll admit I fell in love with Kim, 'round the same time she had fell in love wit' him.” They soon went public with their relationship. Kim said, “Kanye and I have been friends for years, and you never know what the future holds or where my life will take me.” (Today)

1 Kim Kardashian & Kris Humphries (Enemies)


Kim Kardashian and Kris Humphries were in one of the most famous and shortest marriages in Hollywood history. There have been a few marriages that were shorter but none ended in such spectacular fashion. However, Humphries did become world famous for his marriage to Kardashian. They married in grand fashion in October 2011. The build-up to the wedding was documented in Keeping Up with the Kardashians. The wedding ceremony itself was featured in a special two-part television event. Kim even released a fragrance, Kim Kardashian Love, in conjunction with the wedding.

However, after only 72 days of marriage Kardashian filed for divorce. After the divorce was finalized, Humphries noted he was suspicious that Kim was interested in Kanye West. They were accused of faking the whole marriage for ratings but they both denied that. In 2017, Kim pointed out that she felt pressured at the time to get married because of her age. She said, “I'm 30 years old, I better get this together, I better get married. I think a lot of girls do go through that where they freak out thinking they're getting old and have to figure it out, all their friends are having kids. It was more of that situation.”(DailyMailUK)

Sources: elitedaily

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