In Love, Engaged, Forgotten – These Hollywood Stars Were Together Once

Hollywood as love roulette: one man’s joy is another’s sorrow – and vice versa. This is especially true when choosing a partner for the stars. You can lose track of things in the dream factory.

The possibilities in Hollywood are almost endless. And that doesn’t just apply to singing and acting careers. Because Hollywood not only brings romances to the big screen but also brings celebrities together in pairs in real life. After all, there are many ways to find potential partners: Joint shooting, award ceremonies, parties, and charity events. In the chaos of love in the dream factory, you can lose track of things. Who went with whom again? Who married whom before or after?

Charlize Theron & Keanu Reeves

Charlize Theron & Keanu Reeves

In 1997 they stood together for the first time in front of the camera for the film On behalf of the devilCharlize Theron and Keanu Reeves. Both Hollywood stars are considered shy and reserved – maybe that’s why a close friendship has developed between the two. You never wanted to risk an affair, there were still rumors. In 2011 they then confirmed that they were a couple. However, the relationship did not last long.

A never-ending love story?

On Reeve’s birthday, Theron posted a photo together on Instagram on September 9, 2020, and wrote: “I love this beautiful person so much. Happy birthday, Keanu. You’re simply the best. ”The Post caused quite a stir in the international tabloid press.

Winona Ryder & Matt Damon

Winona Ryder & Matt Damon

Also, Winona Ryder, who, incidentally, was engaged from 1989 to 1993 with Johnny Depp and Matt Damon have never made their relationship public really. However, the two always appeared together at events and parties for three years. At a Hollywood New Year’s Eve party at the turn of the year 1998/99, it is said to have sparked a lot between Ryder and Damon. In 2000 the “unofficial” couple separated again.

Johnny Depp & Kate Moss

Johnny Depp & Kate Moss

After breaking up the engagement to actress Winona Ryder in 1993, Johnny Depp indulged his love of models again: Before he called the French singer Vanessa Paradis his “soul mate”, he was in a relationship with the British top model Kate Moss for four years. For ex-girlfriend Ryder Depp had “Winona’s” tattooed, which he changed to “Wino forever” during his relationship with Moss. In 1998, however, Moss also parted ways with the well-known movie star.

Alanis Morissette & Ryan Reynolds

Alanis Morissette & Ryan Reynolds

Hollywood beautiful Ryan Reynolds and US singer Alanis Morissette were a couple for five long years. However, the engagement was never followed by a wedding, and the couple did not even set an appointment. Gut feeling – because in 2007 the alleged dream couple separated by “mutual agreement”. In 2008 Reynolds got engaged to US actress Scarlett Johansson and went through the full program this time. The marriage still didn’t last.

Blake Lively & Penn Badgley

Blake Lively & Penn Badgley

Blake Lively and Penn Badgley were not only a couple in the hit US series Gossip Girl, but also briefly in real life. In 2011, however, Lively met and fell in love with the recently divorced Canadian actor Ryan Reynolds while filming Green Lantern. The couple married in 2012 and now have three daughters. For Reynolds, love is now going well, with Lively he is overjoyed.

Matthew McConaughey & Sandra Bullock

Matthew McConaughey & Sandra Bullock

During the filming of The JuryMatthew McConaughey and his film partner Sandra Bullock, who played law student Ellen Roak, get together in 1996 and become a couple. Their relationship lasts five years. It wasn’t until 2007 that McConaughey fell in love again and married the Brazilian model Camila Alves in 2012, with whom he had three children. However, he and Bullock are still good friends.

Ryan Gosling & Sandra Bullock

Ryan Gosling & Sandra Bullock

Sandra Bullock comforts herself with newcomer Ryan Gosling after separating from Matthew McConaughey. In 2001 the two announced that they were a couple – not without headlines. Because Bullock is over 17 years older than Hollywood beau Gosling. Their relationship lasts two years.

Ryan Gosling & Rachel McAdams

Ryan Gosling & Rachel McAdams

During the filming of Like a Single Day in 2004, Ryan Gosling met and fell in love with US actress Rachel McAdams shortly after separating from Bullock. From then on, the two of them hit the headlines again and again with smooching scenes – for their film kiss in the Nicholas Sparks drama, the two even win the MTV Movie Award for the best kiss scene. In 2007, the wild kissing is over, the engagement is broken up spontaneously.

Ryan Gosling & Eva Mendes

Ryan Gosling & Eva Mendes

Ryan Gosling has always been said to have a penchant for older women. After his relationships with Bullock and McAdams, the Hollywood blatant press has found its acceptance confirmed. Gosling is dating US actress Eva Mendes after filming together for The Place Beyond the Pines – she is older than him again. Bradley Cooper can also be seen on the left in the picture, which was taken at the film premiere of “The Place Beyond The Pines”.

Ashton Kutcher & Demi Moore

Ashton Kutcher & Demi Moore

Hollywood beauty Ashton Kutcher also has a preference for older women: in 2003 he met 16-year-old Demi Moore. The two married in 2005 and also maintain a friendly relationship with Moore’s ex-husband Bruce Willis. In 2011, Moore announced the breakup amid reports of Kutcher’s affair circulating. January Jones, US actress, and Mad Men star was dating Kutcher back in 2001. When she announced her pregnancy in 2011, Moore’s ex-husband was traded as a potential father.

Mila Kunis & Macaulay Culkin

Mila Kunis & Macaulay Culkin

US actress Mila Kunis was in a relationship with Kevin home alone child star Macaulay Culkin for eight years. She and Ashton Kutcher had known each other since we were teenagers from filming the US sitcom The Wild Seventies. Their long friendship turned into love in 2012. In 2015, Kunis and Kutcher even got married and now have children together.

Kirsten Dunst & Jake Gyllenhaal

Kirsten Dunst & Jake Gyllenhaal

In 2004, US actors Kirsten Dunst and Jake Gyllenhaal appeared together as a couple at the Vanity Fair Oscar Party in Hollywood. After only two years, the two separated – at least Gyllenhaal quickly found a replacement.

Natalie Portman & Jake Gyllenhaal

Natalie Portman & Jake Gyllenhaal

The two were inseparable: Natalie Portman twisted Brokeback Mountain -Star Jake Gyllenhaal, 2006 let the head. They were considered Hollywood’s dream couple but separated after only a year of the relationship. Gyllenhaal was then in a relationship with US actress Reese Witherspoon from 2007 to 2009.

Nicolas Cage & Lisa-Marie Presley

Nicolas Cage & Lisa-Marie Presley

For four years, US actor Nicolas Cage and the only daughter of the “King of Rock’n Roll” Elvis, Lisa Marie Presley, were a couple. In 2004, the two were romantically and media-effectively married in Hawaii under the palm trees – after only three months, the divorce followed. Presley gave “irreconcilable differences” as the reason.

Madonna & Sean Penn

Madonna & Sean Penn

You, a mega pop star, and he, one of Hollywood’s most celebrated actors. Madonna and Sean Penn are rightly considered one of the most glamorous couples of the 1980s. For four stormy years, the two were in a relationship and even married. The wedding turned into a media event, like Andy Warhol, Cher, and Tom Cruise was among the guests. In 1989, Madonna files for divorce because Penn is said to have threatened her with fists. Penn called the marriage a “big mistake” much later. Nonetheless, the fronts are clear today and the two are friends, so they were photographed together at a gala in 2016.

Brad Pitt & Gwyneth Paltrow

Brad Pitt & Gwyneth Paltrow

They were once considered Hollywood’s dream couple and even wanted to get married. The US actors Brad Pitt and Gwyneth Paltrow were engaged from 1995 to 1997, but they never had a dream wedding. Paltrow parted ways with Pitt shortly before. She officially stated that the reason for separation was that she was not yet ready for marriage. As a sought-after Hollywood beau, Pitt did not stay alone for long and eventually married Jennifer Aniston. After an ugly divorce, he married Angelina Jolie.

Gwyneth Paltrow & Ben Affleck

Gwyneth Paltrow & Ben Affleck

After the engagement to Brad Pitt broke up, Gwyneth Paltrow met and fell in love with US actor Ben Affleck in 1998. Together, the couple even shot the romance film Bounce – A Chance for Love. After almost three years, they ended their relationship in 2000. Another three years later, Paltrow was ready for marriage: On December 5, 2003, she married the singer Chris Martin, the frontman of the British band Coldplay.

P.Diddy & Jennifer Lopez

P. Diddy & Jennifer Lopez

At that time, Jennifer Lopez was still relatively unknown, but in 1999 she caught the successful US rapper, P.Diddy. Accompanied by superstar Sean “Puffy” Combs and dressed in a daring designer dress, J.Lo drew everyone’s attention at the 42nd Grammy Awards in 2000. Their relationship lasted only two years, but Father Diddy confessed in 2009 that J.Lo was the love of his life.

Jennifer Lopez & Ben Afflack

Jennifer Lopez & Ben Afflack

Shortly after separating from US rapper P. Diddy, Jennifer Lopez and Ben Affleck fall in love. The pop diva already had two divorces when she got engaged to Affleck in November 2002 after only a few months. The tabloid press celebrates the couple under the name “Bennifer”. J. Lo confesses in an interview much later: “It was a sincere love between us.” The relationship between the singer and the actor did not last. In 2004 Lopez married the singer Marc Anthony.

Jim Carrey & Renee Zellweger

Jim Carrey & Renee Zellweger

This couple falls into the “in love – engaged – forgotten” category: But Jim Carrey and Renée Zellweger were also once a couple. The two actors met and fell in love in 1999 while filming the film Me, Myself & Irene. The press celebrated Carrey and Zellweger as the Hollywood dream couple. The two were together for about a year and even briefly engaged. When the joint film was released in 2000, the couple split up.

Paris Hilton & Nick Carter

Paris Hilton & Nick Carter

At that time, hotel heiress and party girl Paris Hilton changed her men like her socks: From December 2003 to July 2004 she was with ex- Backstreet boy Nick Carter. After seven months, the two supposedly split up “amicably”. Carter had his famous “Paris” tattoo tied – into a skull and the slogan “Old habits die hard” (German: “Old habits are difficult to shed”).

Britney Spears & Justin Timberlake

Britney Spears & Justin Timberlake

Even Britney Spears this has been confirmed by both but never – was said to have even an affair with Nick Carter. The absolute musician dream couple of the Millennials were probably Britney Spears and Justin Timberlake. The two singers had known each other since childhood from the US TV show Mickey Mouse Club. Their separation in 2002 made international headlines. To this day, both should not be easy to talk to each other. Shortly after the split, Timberlake landed a world hit with Cry Me a River. In the song, he should have processed the relationship with his ex.

Britney Spears & Colin Farrell

Britney Spears & Colin Farrell

The separation from childhood sweetheart Justin Timberlake was not easy for Britney Spears either. At the zenith of her career, the young pop princess is said to have had countless short affairs with other celebrities. These include Boyz-N-Girlz United singer Robbie Carrico, Limp Bizkit frontman Fred Durst, and actor Jared Leto. Even Colin Farrell to the better half of 2003 briefly Spears have been.

Justin Timberlake & Alyssa Milano

After breaking up with Britney Spears, Justin Timberlake wasn’t a sad child either. So some relationships with celebrity women followed until he settled down with US actress Jessica Biel in 2007. In 2002 the successful singer was with Charmed star Alyssa Milano. According to her statements, she was his big crush, but the relationship between the two did not even last a year. Today Milano is happily married, too, but indulging in memories on Instagram.

Justin Timberlake & Cameron Diaz

Justin Timberlake & Cameron Diaz

Justin Timberlake throws himself into the next relationship shortly after separating from Milano in 2003. This time there is a blonde at his side again – and none other than US actress Cameron Diaz, who is enjoying great international success with comedies like Crazy About Mary with Ben Stiller and the two remakes of Charlie’s Angels. For a good three years, the couple enchanted the public not only with glamorous appearances on the red carpet but also with crisp pictures of surf excursions together. They ended their relationships in 2006, but are still good friends today.

Alyssa Milano & Eric Dane

Alyssa Milano & Eric Dane

Hollywood’s love roulette continued to turn for Charmed star Alyssa Milano. After separating from Justin Timberlake, she met actor Eric Dane on the set of the US mystery series 2003. Dane leaves the series after a few guest appearances. The magic between him and Milano also evaporated quickly.

Tom Cruise & Cher

Tom Cruise & Cher

Cher was already at the peak of her career. Tom Cruise was just getting started in Hollywood. The 39-year-old pop diva and the 23-year-old young actor are said to have met at a charity event in the White House. Decades later, Cher unpacks in 2006 with US talk show host Oprah Winfrey about the Techtelmechtel. It was just wonderful, she was so crazy about Cruise.

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Tom Cruise & Nicole Kidman

Tom Cruise & Nicole Kidman

For Hollywood standards, their relationship lasted an unusually long time:  Tom Cruise and  Nicole Kidman were the dream couple for eleven years. But in 2001 the love ended suddenly. Cruise filed for divorce. But her Turtel appearance at the 45th Cannes Film Festival, where you could still admire Kidman in 1992 without botox and with her natural, red curls, will not be forgotten.

Nicole Kidman & Lenny Kravitz

Nicole Kidman & Lenny Kravitz

After the divorce from US actor Tom Cruise, Nicole Kidman discovered her passion for musicians. Hard to believe, but true: Australian rocker Lenny Kravitz is dating in 2003. Because of Kravitz’s alleged infidelity, the relationship between the two quickly breaks down. The Oscar winner separated from the rocker in 2004 and married country star Keith Urban shortly afterward. Lenny Kravitz, who was with Kylie Minogue among others in the early 1990s, still gets along great with his ex Kidman, as pictures from 2016 prove.

Diane Kruger & Josh Hartnett

Diane Kruger & Josh Hartnett

Their relationship has also been completely forgotten: in 2004, German actress Diane Kruger and Hollywood beau Josh Hartnett fell in love. They met on the set of Longingly. The relationship only lasted a few months, despite public turtles.

Vanessa Hudgens & Zac Efron

Vanessa Hudgens & Zac Efron

Very young and successful: the two young actors Zac Efron and Vanessa Hudgens got off to a flying start with the internationally successful Walt Disney production High School Musical. When filming the first part, there was a lot of spark between the two. Not only on screen but in real life too, teenagers languished. From 2005 to 2010, Efron and Hudgens, the lovers of Hollywood.

Vanessa Hudgens & Josh Hutcherson

Vanessa Hudgens & Josh Hutcherson

Shortly after separating from Zac Efron, Vanessa Hudgens again has a sought-after young actor by her side. Your relationship with Hunger Games star Josh Hutcherson should remain a secret for now. Hutcherson just can’t keep his feelings in check and 2011 publicly confesses his love for Hudgens. Too hasty, it turns out, because their relationship only lasts a few months. Even after the breakup, the couple is still promoting their joint film The journey to the mysterious island in a very professional manner.

Edward Norton & Salma Hayek

Edward Norton & Salma Hayek

In the mid-1990s, US actor Edward Norton was dating Kurt Cubain’s widow Courtney Love. In 1996 they met while filming together, but quickly separated because they were fundamentally different personalities. Norton found a like-minded partner in Salma Hayek. Frida took Norton therefore not only a role but also helped her in the revision of the script in Hayek film.

Angelina Jolie & Jonny Lee Miller

Angelina Jolie & Jonny Lee Miller

It seems like an eternity and a few marriages ago: After almost two years of relationship, US actress Angelina Jolie married her British actor Jonny Lee Miller in 1996. The two first met in 1995 on the film set of Hackers – In the FBI network Times. The divorce followed in 1999, but Jolie and Miller have remained good friends to this day and still enjoy posing together in front of the camera. Allegedly, Sienna Miller is said to have taken Jolie’s husband off at the time. Years later it is said Jolie is said to have taken Brad Pitt off Jennifer Aniston. That’s how it goes in Hollywood …

Sienna Miller and Jude Law

Sienna Miller and Jude Law

In the tabloid press, the couple was more than present at the time, but their relationship now seems to be forgotten. There was a constant back and forth between Sienna Miller and Jude Law. Sometimes the actors were together, sometimes they weren’t. The relationship chaos lasted for almost ten years. Miller and Law met – and love – on Alfie’s set in 2004. From then on, the two had an “on-off” relationship – until 2011 finally – finally – was over.

Channing Tatum & Amanda Bynes

Channing Tatum & Amanda Bynes

During the filming of the teen romance, She’s the Man, Hollywood beau Channing Tatum and Amanda Bynes met in 2006 – and apparently, they hooked up too. The two not only cuddled and smooched on the big screen but also at the after-show party of the film premiere. The relationship between the two does not last long, as Tatum met Jenna Dewan while filming his next film Step Up. He married her three years later.

Taylor Lautner & Lily Collins

Taylor Lautner & Lily Collins

Between Phil Collin’s daughter and Twilight star Taylor Lautner, it should have crackled in 2011. Lily Collins and the acclaimed up-and-coming actor met while filming the thriller Abduction. The result: a brief romance that did not go unnoticed by the tabloid press. However, they have never publicly confessed to their affair.

Debbie Lentz
Accomplished Global Supply Chain executive with significant experience in the consumer products and retail industries with large brand name firms in the public and private sectors. Strategic and operational, drives change and creates efficiencies through integration of end to end process improvement focused on enhancing the customer experience and fostering company growth. Collaborative leader with high integrity who builds talented, results-oriented teams.

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