We tend to think that celebrities have absolutely everything that anyone could have in life. We think that they’re beautiful, wealthy, successful, and can do whatever they want whenever they want. It’s kind of tough not to think that way, right? They definitely seem to have it all going on.
Of course, we know that celebs are still human beings, and they go through tough times like the rest of us. Money can’t stop heartbreak or loss or health issues. That’s just not the way that it goes. Sure, there are a lot of actresses and singers who have had hot and heavy romances for ages, and we always look up to those couples since we think that they are totally #relationshipgoals. But there are some stars who always seem to be single or who are always breaking up with someone and dating someone new. When it comes to which celebs can’t seem to stay in a long-term relationship, there are definitely a few that are pretty unlucky in love. Check out the 15 super successful stars who fail hard at relationships.
15. Vanessa Hudgens: Is “fed up” and jealous
She and Zac Efron had a serious thing and then a bad break-up. For a while there, though, they really seemed like they were going to go the distance. Sure, they were super young and people grow and change, but still.
Vanessa and Zac were together from 2010 until 2015. She has been dating actor Austin Butler since 2011, so her luck has turned around, but most people still think of her as having had a failed relationship with Zac. Their love story was basically the definition of high-profile. The press could never stop talking about them. What went wrong? Well, they haven’t stayed friends, since she has said that they don’t talk anymore. She told The Daily Mail that she was “fed up” with how girls absolutely loved Zac. So maybe his good looks and fame were a factor in the dissolution of their love.
14. Taylor Swift: Everybody can see the crazy
Love her or not, we have to admit that the pop star has had a lot of failed relationships. None of her relationships have worked out so far and it seems like every time we log onto Twitter or read the entertainment news, she’s dating someone new.
We all know that she writes songs about her ex-boyfriends or guys that she dated briefly. People don’t see her as being lucky in love, that’s for sure. Some of the famous exes on her list include Harry Styles and Jake Gyllenhaal. She was in a serious relationship with Calvin Harris from February 2016 until the summer of 2016, but then things went downhill. She started dating Tom Hiddleston soon after but that didn’t work out, either and they were only together for about three months. Will Taylor find love soon? Fans would definitely love to see her in love and have it last… but would she have anything to write about?!
13. John Mayer: Doesn’t respect women enough
The guitar-playing singer definitely has more of a playboy reputation than of a hopeless romantic… although, that being said, there is nothing more romantic than a guy who plays the guitar. Just saying.
John Mayer famously dated Katy Perry but it didn’t work out. There was a lot of drama surrounding that break-up, especially when she was quoted as saying that he was her best “lover.” We would think that would be music to John’s ears (yup, that was a bad music pun…) and yet he didn’t seem thrilled to hear that. When he was interviewed by Rolling Stone, he said, “I don’t have a cool enough thought for you. “I’ve hacked this game. I pay very little of the price of fame now. I get to play the music that moves me the most. I’m having the time of my life. I’m 39 — I remember 32. I don’t wanna do it again.” Okay then!
12. Jennifer Lopez: So many engagements, so little husbands
The triple threat star had several high-profile relationships but seems to be single again every few years. Who could forget when she dated Sean Combs/P. Diddy from 1991 until 2001… and then she married Chris Judd (who was her backup dancer) in 2001… and then dated Ben Affleck from 2002 until 2004? Sadly, none of those relationships or marriages worked out.
Jennifer started seeing Marc Anthony in 2004 and they broke up in 2011. That must have been pretty devastating since that romance seemed like it was for the long run. The two singers were super cute together and they even have twins together. Jennifer dated another backup dancer, Casper Smart, from 2011 until 2016. She has been linked to Drake but it’s not super clear if they were really dating or what was going on.
11. Kristen Stewart: Flip flops way too often
The Twilight star and indie movie staple had a very public break-up with Robert Pattinson when she cheated on him with her older director. Remember what a scandal that was?! There is nothing like a Hollywood cheating scandal to get people talking.
Kristen and Robert stared dating in 2009 and the scandal happened in July 2012. Since then, the actress hasn’t really been linked to anyone. But it’s totally possible that she has dated a lot of people but has stayed private about it. After all, she seems like a pretty private person and she has spoken out about not loving the trappings of fame and not enjoying interviews or press. That’s totally her right, of course, even though we tend to think that every famous person should love being famous.
10. Ben Affleck: Cheaters never prosper
Ben Affleck’s career has been going strong for a while, but his marriage to Jennifer Garner hasn’t lasted. The news that the two were splitting up was super shocking to pretty much everyone since that never seemed like something that could happen. They just seemed so happy together.
So what went wrong? There have been a ton of rumors flying around, as is usually the case with this type of thing. People have said that Ben cheated on Jennifer. Others have said that it just didn’t work out (which is super helpful… not). There has also been chatter that Ben has suffered from addiction issues for a while and Jennifer wanted him to go to rehab. We will probably never really know what happened, but one thing is for sure: Ben’s romantic life hasn’t been as successful as his acting career.
9. Britney Spears: Nobody can hold her down
Let’s face it, we all love the …Baby One More Time singer. We probably grew up listening to her super fun pop music and might even still put it on from time to time when we feel like getting nostalgic. We all loved seeing Britney Spears and Justin Timberlake as a couple back in the day, especially when they wore matching denim on that one infamous, glorious day.
But they didn’t last, and unfortunately, Britney hasn’t been that lucky in love since then. She has been married twice and each marriage was super short. She married Jason Alexander (who was her friend, not the actor who played George on Seinfeld) and it lasted 55 hours. Yup. 55 hours. Then she tied the knot with Kevin Federline in 2004 after they were seeing each other for three months. They got divorced in 2006. Brit has been linked with a few guys since but doesn’t seem to have found true love yet. We’re rooting for her!
8. Jon Hamm: Way too complicated for relationships
Most of us loved Mad Men and one person who made the show so great was Jon Hamm, thanks to his portrayal of complicated bad boy Don Draper. It seemed like everything was going well for him in his life: great acting career and amazing long-time girlfriend, Jennifer Westfeldt.
Unfortunately, the two of them broke up in 2015 after being together since 1997. Yup, that was a really long time. What went wrong? The break-up happened around the time that news broke about the actor’s troubled past, so it seems like maybe those two things were connected. In March 2015, it came out that the actor was in rehab for alcoholism, and in April 2015, it came out that he had hazed other students back in college and was charged for it.
7. Christina Aguilera: has a hard time holding on to relationships
The singer with one of the most gorgeous, amazing voices ever has been engaged for a few years now, so it seems like things are looking up romantically for her.
But she has a failed marriage under her belt and has been in a few relationships, so she is someone who has had some tough times when it comes to romance. Like we all have, of course. It just goes to show that even the wealthiest and most successful people out there can go through break-ups and divorce and hard times. They really aren’t that different from the rest of us (well, besides all the dough that they have). Christina married Jordan Bratman in 2005 and their divorce was final in 2011. She is now engaged to Matthew Rutler.
6. Justin Bieber: Bedding half of the Instagram models out there
We all love the music of The Biebs… whether or not we’re going to admit it or not. There’s nothing to be ashamed of because his music is really fun but, hey, some people still see it as a bit of a guilty pleasure.
Justin famously had an on-again, off-again relationship with Selena Gomez. They were honestly super cute together. Lots of fans totally think that he still loves her. He doesn’t seem to have had much luck in love since they broke up. They were together for basically six years from 2010 until 2016 but since 2016, it seems like they are over for good. Which, again, sucks for fans who still think that the love is in the air for the two singers.
5. Lady Gaga: Men are way too intimidated by her
When Lady Gaga dropped her most recent album Joanne, she revealed some personal things about herself, and even left the meat dresses and crazy costumes behind to show off the real her. Fans got to see a new side of her in the amazing Netflix documentary Lady Gaga: Five Foot Two as well.
The singer has had three very serious, long-term relationships that unfortunately didn’t last. In the doc, she talks about being lonely and having had trouble with heartbreak. She dated Luc Carl, who owns a bar, back in 2005, and they got back together in 2010. She was then with Matthew “Dada” Williams who works for her company Haus of Gaga. Then, most famously, she was engaged to actor Taylor Kinney, but that broke up fairly recently. Hopefully the next time is the charm for the super talented and cool singer!
4. Demi Lovato: needs to work on herself first
The singer may have an amazing career with tons of musical success, but her longest and most serious relationship ultimately wasn’t successful. The break-up must have been a big surprise to fans.
Most famously, Demi dated Wilmer Valderrama for six whole years and they announced their break up in the summer of 2017. It seemed like a pretty friendly break-up because they both said on Instagram that it was a tough choice but they felt that it was the right thing for them to do because they would be “better as best friends.” Since then, she has dated an MMA fighter named Guilherme “Bomba” Vasconcelos but that only seemed to last a few months and now it’s over. Here’s hoping that Demi’s next love story will have a happy ending!
3. Hilary Duff: Trying her best to bounce back
Hilary Duff seems like a really sweet person. She’s also really talented and is a great pop singer and does an awesome job on the show Younger. But she hasn’t had such good luck when it comes to love.
She’s divorced from hockey player Mike Comrie and is known as a single mom. She often talks about her life as a singer mother and has said that it “sucks” to be divorced. A lot of people consider divorce to be a failure since it’s obvious that it didn’t work out, but really, major props to anyone who realizes what isn’t making them happy and who takes steps to feel better. These days, Hilary is back with her ex-boyfriend Matthew Koma, so things are looking up for the star for sure.
2. Pink: Has the weirdest marriage in Hollywood
Pink has been a steady part of the pop music scene since her first album, Can’t Take Me Home, was released in 2000. She has been married to Carey Hart since 2006 and they have two kids together, but they have actually had a bit of an on-again, off-again thing. Pink has been super honest about that as well.
They got together in 2001 and then broke up in 2003… and got engaged in 2005 and officially got married in 2006… and broke up again in 2008. They finally reunited in 2010 and it seems like things are still going strong. But it definitely wasn’t a peaceful ride and it’s not the fairy tale kind of relationship that a lot of people dream of or think that celebs should have.
1. Sophia Bush: Holding onto the past
We probably all know and love Sophia Bush from her days as Brooke Davis on One Tree Hill. Talk about an amazing and classic teen drama. She has had a successful career since then, starring on Chicago PD and also doing a lot of amazing things for various charities.
But sadly, Sophia hasn’t had the best luck with dating. She was briefly married to her One Tree Hill co-star Chad Micheal Murray but they split up when it came out that he had cheated on her (ugh). She then dated her Chicago PD co-star Jesse Lee Soffer but they split up back in 2015. She has actually dated a lot of co-stars: she was also linked to James Lafferty and Austin Nichols (aka Nathan Scott and Julian Baker on One Tree Hill).
Sources: Ew.com, Theguardian.com
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