10 Most Insanely Awkward Celeb Love Triangles

Hollywood can sometimes seem like a huge orgy; if you follow the tabloids, most would believe that everyone is sleeping with everyone. Although, that may be an exaggeration, there are several cases of celebs hooking up with or all out stealing the boyfriend of their friends, enemies or a perfect stranger. These stories normally end up being chalked full of titillating drama, entertaining enough to make us want to know as much as possible. However, for the parties involved it can be embarrassing, shocking and heartbreaking but worst of all, their entire career can take a hit; it is like being branded with a scarlet letter. Years after Ryan Phillippe was busted for cheating on his then wife Reese Witherspoon, he did an interview where he expressed his hatred for constantly being branded as a cheater and having to deal with interviews with reporters and talk show hosts always wanting to bring up his divorce. On the bright side, his screw up was not as long lasting as say… Chris Brown and Rihanna; these two cannot seem to stay away from one another and to make matters worse, they include their family, friends and potential lovers into their web of deceit. The likes of Drake, Karrueche Tran, Matt Kemp and even Leonardo DiCaprio have all suffered some kind of drama because of the two love birds who can’t quit one another. If you think you have seen drama yet, read on below to see a list of celebrities involved in bizarre, drama-filled, exciting celebrity love triangles. No one can bring the drama like the entertainers themselves.


10 Robert Pattinson, Kristen Stewart and Rupert Sanders

Talk about a burn; these Twilight Saga love birds were together for almost 6 years when Stewart decided to use filming a movie and getting “caught up” as an excuse to cheat on her British hunk. To top it all off, the director who she cheated with Rupert Sanders, was a married man with three children. Their public display of affection set off a whirlwind of rumors that sent off red flags for the significant others. The awkwardness of looking at pictures of your girlfriend or husband passionately kissing and feeling each other up is clearly a hard thing to swallow. Needless to say, it ended badly for both parties; Pattinson moved on to a more put together chick, and Sanders, well his wife divorced him.

9 Nikki Reed, Ian Somerhalder and Nina Dobrev

Nikki Reed and Nina Dobrev used to be pretty good friends, but unfortunately, things got weird when Reed and Ian Somerhalder (Dobrev’s ex boyfriend and The Vampire Diaries co-star) were spotted frolicking and holding hands in LA. Although Dobrev has stated that she is fine with the romance, it still must be hard to see someone who you dated exclusively for several years hooking up with someone you called a friend. The new couple has been rubbing their love in everyone’s face, starting off with matching tattoos, then adopting a dog together, moving in together, oh and now getting married. This whole thing has got to be awkward to watch for Dobrev; maybe that’s why she quit The Vampire Diaries.

8 Kendall Jenner, Justin Bieber and Selena Gomez

Recently a photo was released showing Kendall Jenner and possibly Justin Bieber, in a bed together; unfortunately, this was no accident. In fact, Kendall Tweeted the picture herself. It is safe to assume that this will draw a wedge between Kendall and her soon to be ex-friend Selena Gomez; we all know that Gomez and Bieber have had a tumultuous on again, off again relationship that continuously seems to disrupt not only their lives but the people around them. Kendall better watch out though, as Selena seems like the vengeful type ex-girlfriend who is not afraid to put her hands on someone. To make matters worse, sources are reporting that this romance has been blossoming since 2014 Coachella.

7 Demi Moore, Ashton Kutcher and Mila Kunis

Ashton Kutcher seemed to be head over heels in love with his wife Demi Moore, but it looks as though the cougar-love wore off when he re-kindled his friendship with That 70’s Show cast-mate Mila Kunis. Kutcher quickly left Moore for Kunis but he did not intend for Moore to hang on by any thread she could. This love triangle got awkward when Moore decided that she needed to meet and hold Kutcher and Kunis’ baby girl, Wyatt. In addition, Moore is apparently constantly calling and texting Kutcher asking for updates on Wyatt and she showed up to the baby’s Kabbalah blessing. This whole situation is weird but who knows, maybe Kutcher is the one who keeps inviting her over to observe his new family.

6 Shar Jackson, Kevin Federline and Britney Spears

When mega-star Britney Spears hooked up with Kevin Federline (one of her back up dancers) the world was more than stunned. Who was this guy? Where did he come from? And what was appealing about him? Well, it turned out he was actually a practically married man with 3 kids and 1 on the way (technically he was only biological father to 2 of those kids). So, where does it get really sticky? It was reported that Shar Jackon was just as shocked as the rest of the world to see her fiance booed up with the pop star, while she was a couple months pregnant. Awkward!!!

5 Laura Dern, Billy Bob Thornton and Angelina Jolie

Remember when Angelina Jolie was married to Billy Bob Thornton? You know they guy whose blood she had in a vial around her neck. That pairing in itself was awkward (Thornton even admitted to feeling like Quasimodo during their relationship); well to make things slightly more uncomfortable, Thornton was engaged to Laura Dern at the time. So every photo you see of Thornton and Jolie during the beginning of their relationship, well yes, he was yet to break things off with Dern. Dern has said she too was blown away by his infidelity, stating; “I left our home to go and make a movie and while I was away, my boyfriend got married and I never heard from him again.” That has got to hurt.

4 Karrueche Tran, Chris Brown and Rihanna

Does anyone feel bad for Karrueche Tran? Come on, time and time again she takes Chris Brown back and apparently she has not learned that Rihanna will always be waiting in the wings; and will always win. This love triangle is more like a love circle; RiRi dates whoever she wants, Brown dates Tran and when Rihanna is bored, she starts Tweeting, Instgramming and calling Brown to hang out. There have been several incidents where Brown and Rihanna have been caught in public looking slightly lovey-dovey, while Tran is on vacation or waiting at home for her misfit man. Is she not tired of being embarrassed? Sometimes even Drake gets into the mix (hence the circle not the triangle). It is just one big embarrassing mess.


3 Hilary Duff, Aaron Carter and Lindsay Lohan

Ahhh young love; it can be downright dirty, especially when your friend and sometimes cast mate steals your man. Lindsay Lohan and Hilary Duff used to be Disney channel cuties together until a young Aaron Carter broke up the friendship. Duff was dating Carter first; the relationship was well documented and had everyone questioning marriage, however, Carter must have fallen under the red-head spell because he quickly packed up after almost two years and moved right on to Lohan, sparking a feud that is still ignited to this day. Carter and Lohan started showing up to the same events as Duff together, and acting so in love it was sickening. He eventually left Lohan and tried to re-kindle what he had with Duff, but he cheated on her again (apparently with her best friend). Now both ladies are Aaron-less and quite frankly better off.

2 Reese Witherspoon. Ryan Phillippe and Abbie Cornish

America’s sweetheart Reese Witherspoon basically put Ryan Phillippe on the map; yes, he had Cruel Intentions and I Know What You Did Last Summer but let’s face it, he has not done much worth mentioning since then. His marriage to mega-star Witherspoon was a blessing in disguise for him, that is until be mucked it all up with his wandering eye. Phillippe was spotted canoodling with a then unknown actress, Abbie Cornish (still kind of unknown). Witherspoon divorced Phillippe, who quickly shacked up with Cornish until that eventually fizzled out. Was it worth it Ryan? No really, was it? Inquiring minds would love to know.

1 Drake, Rihanna and Chris Brown

Brown and Rihanna had a fairy tale relationship (seemingly) until he decided to do the unthinkable, you know the incident before the Grammy’s back in 2009. Well ever since then, Drake has been trying to pick up the pieces even as Rihanna floated between the two of them, trying to figure out if she was strong enough to leave Brown. Not one to give up and maybe a bit smitten, Drake till this day has a back and forth relationship with RiRi that has made things awkward. Drake and Brown have apparently gotten into physical altercations because of Rihanna, and scrapped a collaboration (which most likely would have been great); all this to show loyalty to one girl who has been dating around during all of this. How awkward is it to fight over a girl who is actively dating other men and trying to move on with her life?



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