When it comes to relationships, we generally agree with the idea that nobody really knows what a relationship is like except for the couple themselves. Although that is true, both for our next-door neighbors and for celebrity couples alike, the truth is that sometimes it is possible to look at a relationship and know something is just not quite right there. Celebrity relationships can be fun topics for gossip fodder (let’s all admit we are totally obsessed with Taylor and Travis at the moment) but sometimes they can be also be downright problematic.
From relationships with age gaps that range from eyebrow-raising to downright illegal to relationships that just seem toxic or even abusive, these celebrity pairings were destined to end badly. Some of these problematic relationships ended on the covers of the tabloids, and some ended up with criminal charges, but all of them leave us wondering what the celebs involved were thinking! Read on for our judgmental round-up of celebrity relationships that were all too messy and downright problematic.
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Jerry Seinfeld and Shoshanna Lonstein
Jerry Seinfeld was 38 years old when he met Shoshanna Lonstein, then 17 and STILL IN HIGH SCHOOL, in a park and got her phone number. They ended up dating for four years, but that doesn’t make it OK in our book. Attention adults of the world, including celebs: High schoolers should only be dating high schoolers.
Taylor Swift and Conor Kennedy
We love Taylor and we generally support her dating life, especially when it results in some of our favorite songs. That said, we have to note that she also broke the rule about not dating high school students as an adult. In 2012, she briefly dated Conor Kennedy (yes, one of those Kennedys), who was still in high school.
Taylor was 22 at the time and Conor was 18, so it wasn’t illegal, just a little too much of an age gap for that stage of her life. It also led to rumors that she was only dating him because she was obsessed with the famous family, which wasn't helped when she also bought a mansion near his family shortly after starting to date him.
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Kanye West and Bianca Censori
We have no doubt that being married to Kanye West isn’t an easy assignment and, honestly, we worry about his current wife, Bianca Censori. Since getting together with the rapper, her whole appearance has changed, she’s regularly photographed in public barely dressed, and she never looks happy or comfortable. (Wearing nylons as pants might not help with that.) We hope she is OK.
Kylie Jenner and Tyga
The nice thing about the Kardashian universe is that there is always more than one problematic example for any list we are going to make. Kylie and Tyga end up here because they are yet another example of a couple who got together before everyone was an adult. Tyga is seven years older than Kylie, and the two started dating before she turned 18, after meeting at her 16th birthday party.
The two have claimed they didn’t hook up before she was 18, but nobody actually believes that, especially because he hosted her 17th birthday party at his house and got a tattoo of her and gave her a $322,000 Ferrari as a gift. That doesn’t exactly shout “just friends,” does it?
Chris Brown and Anyone
Singer Chris Brown has a long dating history, including his explosive relationship with Rihanna. Since the 2009 incident when he pleaded guilty to beating Rihanna so severely she required hospitalization, he has been accused of rape, had a subsequent girlfriend file for a restraining order after he threatened her, been accused of threatening a different girlfriend with a gun, and been involved in several fist fights and brawls, including with Drake. We’re not sure he’s capable of having a nonproblematic relationship, honestly.
Mike Tyson and Robin Givens
Another celebrity relationship where domestic violence played a role was in the marriage between boxer Mike Tyson and actress Robin Givens. The two were married for only about a year, but Tyson admitted he was violent with her and accused her of being a gold digger and trapping him into marriage.
Justin Bieber and Selena Gomez
Justin Bieber and Selena Gomez were a young Hollywood “it couple” but their relationship was messy and turbulent. The pair broke up and got back together several times before Justin married Hailey Baldwin. Both accused the other of cheating and breaking the other's heart. Both would end up recording diss songs believed to be about the other, which may be the best things that came out of their young love.
Britney Spears and Justin Timberlake
These two seemed like a couple made in pop music heaven, but anyone who has read Britney’s memoir knows that Justin was both a jerk to her during their relationship and then made himself more famous afterward by accusing her of cheating and making crass comments about their sex life. Not cool, Justin.
Johnny Depp and Amber Heard
Yikes, this one was MESSY. Johnny Depp and Amber Heard’s relationship was filled with turmoil, accusations of domestic violence and drug use by Depp, and that whole “Did she poop in the bed?” situation. We know all about it, of course, because their dirty laundry got aired out for the whole world when the two sued each other for defamation.
Blac Chyna and Rob Kardashian
Problematic relationships aren’t just for Kardashian women. Blac Chyna and Rob Kardashian’s relationship included accusations of cheating, drug use, and major fights. Rob leaked nudes of Blac Chyna as an awful act of revenge porn, and Blac Chyna even ended up suing his mother and some of his sisters. Not a happy ending for anyone involved.
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Larsa Pippen and Marcus Jordan
This one isn’t so bad compared to some of the others on the list because everyone involved is an actual adult. But it is certainly a little complicated that Larsa Pippen (Scottie Pippen’s 49-year-old ex-wife) is dating Marcus Jordan, the 32-year-old son of Michael Jordan, who was Scottie’s former teammate. Rumor has it that Michael is NOT a fan of this relationship.
Tom Cruise and Katie Holmes
Tom Cruise and Katie Holmes had a whirlwind romance (including that memorable appearance on Oprah's talk show) that led to their wedding and birth of daughter Suri. Then Katie bolted, basically overnight, and it doesn’t appear that Tom has any relationship with Suri. We’re not sure what went down and what role Scientology played, but we sure would like to know. Something problematic must have happened, but we may never know what.
Angelina Jolie and Billy Bob Thornton
When they were together, Angelina Jolie and Billy Bob Thornton were all about talking about their sex life on the red carpet, swapping blood with each other, and all sorts of PDA. They also had a 20-year age gap, and their marriage started when Billy Bob was still dating actress Laura Dern. They were a mess, but at least it seems like they had some fun along the way.
Kim Kardashian and Ray J
Kim K and Ray J dated for three years, and during that time they both cheated on each other but reconciled enough to film a sex tape. The two have hurled accusations about that famous tape ever since, with Kim claiming it was stolen and Ray J saying that Kim (and her momager Kris) were actually responsible for leaking it. There is definitely no love lost between these two.
Angelina Jolie and Brad Pitt
When they were together and happy, Angelina Jolie and Brad Pitt were perhaps the most ridiculously good-looking couple in Hollywood. But their relationship had a problematic start (there was that little detail of him being married to Jennifer Aniston at the time) and a problematic ending, as their divorce took more than seven years to settle and got very heated with accusations of problem drinking, abuse, and shady business dealings.
