Look Back At 50 Of Hollywood’s Most Famous Romantic Entanglements!

All the best actors and pop stars in Hollywood don’t rise to fame with just talent. Other than their best-selling albums and their award-winning performances, they also have their private lives to share with the public. One of the juiciest topics, of course, is their love lives. The chain behind who is dating who (after who) always piques the interest of fans everywhere. We know that the degree of followers of famous love teams always seems to go beyond what is expected. Even fans choose sides when the famous love triangles come to light. In this list, we have prepared the hottest love affairs and entanglements that Hollywood has ever seen. From teen heartaches to marital problems, we’ve got it all. Most of these will ring a bell, especially if you’ve been in the loop all these years. We might just surprise you, though, because some of these catfights happened under one roof. Are you ready for some sweet gossip? Sit back, relax, and enjoy this rundown of Hollywood’s most famous romantic entanglements served sizzling hot.

Jennifer Garner, Ben Affleck, The Nanny

Jennifer Garner and Ben Affleck were a couple that made so many hearts swoon as their relationship bloomed in front of our eyes. Our hearts were broken when we heard about their separation in June of 2015. They were married for ten years before they decided to split. It was a month after rumors of Affleck having an affair with their nanny named Christine Ouzounian was said to be given credit for the divorce. In a later interview with Vanity Fair, however, Garner denied this, saying that she only heard about the issue with the nanny months after their breakup and that Ouzounian was not part of their choice as a pair. The marital problems may have run deeper, sadly.

Heidi Klum, Seal, Her Bodyguard

Heidi Klum and Seal were married for a while before scandals blew up as Seal started accusing Klum of cheating on him. In a famous interview with TMZ, he said that he thought that if only Klum waited until they were really separated before “deciding to fornicate with the help,” things would have gone smoother. They hired a divorce attorney eventually and called the marriage off. In her interviews after the split, Klum confessed to dating Martin Kirsten, her bodyguard. She said, however, that Seal’s accusations were not true. She only started dating Kirsten after her divorce was processed and then made final. We probably will never know who is telling the truth. Despite that, we hope they’re both happy now, though!

Joe Jonas, Taylor Swift, Camilla Belle

Taylor Swift always knows how to make a headline. In a popular interview in The Ellen DeGeneres Show, she told everyone that Joe Jonas broke up with her in a phone call that lasted only 25 seconds. She said that Jonas’ meeting with actress Camilla Belle should take credit for the breakup. Apparently, his attention was swiped right away as he met someone new, so he couldn’t take longer than 25 seconds to break up with his current girlfriend. The issue blew up, and everyone was talking about it. Matters got even better when Swift wrote and performed the song Better than Revenge, which featured Belle in her lyrics. Jonas got a lot of backlash from what he did to her, too.

Billy Bob Thornton, Laura Dern, Angelina Jolie

This next story is pretty straightforward. Angelina Jolie’s husband before Brad Pitt was Billy Bob Thornton, and he was also in a relationship when she fell for him. It was the late 1990s when Thornton and his girlfriend Laura Dern were living together. According to Dern, in an interview with Talk magazine, she had to leave home for a while to shoot a movie. She had no idea that while she was working, Thornton was already packing up his bags and running away with another girl. She came home to him already married to Jolie. She said she never even heard from him again. What a way to break up with your girlfriend, bud! He sure does get credit for the audacity to leave without warning.

Uma Thurman, Ethan Hawke, The Nanny

The nanny returns again. Apparently, the household help in Hollywood gets better and better as well. Uma Thurman and Ethan Hawke were married for five years when they decided to hire a divorce attorney in 2003. Hawke confessed to have been having an affair with Ryan Shawhughes, the household nanny. In fact, when Thurman moved on, Hawke actually stood his ground and married the nanny. The affair was probably a little deeper than getting naughty. They tied the knot in 2008 and now have two kids together. Now, as husband and wife, they didn’t have to sneak around the house and hide their affection for each other any longer. As for Thurman, she was free to see other people and direct her life somewhere else.

Billy Crudup, Mary-Louise Parker, Claire Danes

Billy Crudup was famous for his portrayal in Almost Famous. He was also famous for dating Mary Louise Parker from The West Wing. The power couple has been together for eight years when Crudup changed his mind about Parker. He left her for Claire Danes, an actress he met on the set of Stage Beauty, even though Parker was seven months pregnant with their son at the time. Danes was also in a relationship with musician Ben Lee when she left him to be with Crudup. The scandalous mix-up got so much attention that the media clearly made it an investment for their stories. Danes admitted to not have been mindful of the aftermath of her actions years later in an interview.

Marilyn Manson, Dita Von Teese, Evan Rachel Wood

American singer Marilyn Manson was dating Dita Von Teese, burlesque performer, back in 2001. The two got married in 2005, but after only one year, Von Teese hired a divorce attorney and called it quits with Manson. Only a very short time after, Manson was seen publicly dating Westworld actress Evan Rachel Wood. Speculations grew, and people tried to piece together what had happened between the three celebrities. Wood shared a while after that she got really affected because people called her a homewrecker for destroying the relationship between Manson and Von Teese. She said she found it hard to get over. Things obviously got messy, and we all saw what happened, but Wood said she never got insusceptible from the backlash.

Ciara, Future, The Wardrobe Consultant

Back in the hip-hop scene, Ciara was engaged to Future and was nursing their three-month-old baby boy when he broke up with her. Apparently, the two singers broke up because Ciara found out that Future had been having an affair with his wardrobe consultant Tyrina Lee. Even while she was with child, he had the audacity to cheat on her behind her back. This news coming from Us Weekly, though, was quickly denied by Future when asked about the topic. He said that he and Ciara grew apart, which was why he decided that it was better for both of them if they were no longer together. He would still need to provide his newborn child with roofing and a good stipend, though.

Kourtney Kardashian, Scott Disick, Sofia Richie

Kourtney Kardashian and Scott Disick were together for quite a long time— long enough for them to have three children together. Fate was not on their side, however, because the couple eventually split. Their children stay with Kardashian, and though the two have been seeing other people, they still keep in touch because of their kids. In the 15th season of Keeping Up with the Kardashians, the two were featured making an investment in co-parenting therapy. Meanwhile, Disick has been dating Sofia Richie since 2017. In the same episode of the show, Disick introduced her to his children. This resulted in Kardashian’s rage for not warning them. Thanks to reality TV, all this was fully documented and aired for our entertainment.

Selena Gomez, Justin Bieber, Hailey Baldwin

Pop stars Selena Gomez and Justin Bieber were a power couple for some time. Although they have been together on and off, most people just assumed they would stay that way for good. Things changed in 2018, however, when they broke up for good in late spring. Shortly after this, Bieber almost immediately started dating Hailey Baldwin and proposed to her in June of the same year. Rumors regarding the third party being the cause of the Jelena breakup surfaced, especially considering the short time it took Bieber to move on. He even placed a huge amount of investment money on the ring he proposed to Baldwin with. The diamond engagement ring was worth $500,000 and was featured on the cover page of Vogue Mexico.