Not every celebrity is hot or even attractive for that matter. There are plenty of rich and famous people who were just not blessed with good looks. And when two unattractive celebs are hooking up or dating, it can be kind of gag-worthy. This is especially true for high-profile celebrities who are in our face all the time in magazines and online. And sometimes, we just don’t want to picture it!
But a lack of good looks is only one of the many things that could make a couple to be worthy of this list. Sometimes, it is just the sheer age difference between them (I am talking as much as 60 years!), or how they portray themselves to the world (devil worshippers or hillbillies, for example). On this list of strange, mismatched celebrity couples whose relationships made us cringe for one reason or another, there are the weirdest of the weird, including murderers, people who married their own child, and even one couple who is so nasty because of the details they spilled in a tell-all episode of their reality show (hint: it has to do with STDs and a “smell”). And the most interesting part of it all is they are all famous people you are very familiar with. Celebrities are just like us — they have skeletons in the closet too, and they are far from perfect when it comes to love and dating.
Get ready to have the image of the perfect celebrity couple shattered, because these 15 very odd famous couples were all involved in crazy relationships that made us gag just a little — or in some cases, a lot.
15. The Grandpa And His Barbie Doll
In relationships, there are age differences, and then there are age differences. The latter was the case for Playboy founder Hugh Hefner and model Crystal Harris. She became his third wife on New Year’s Eve, 2012. The two had been a couple for nearly three and a half years by that point, and they were together until he died this year at the age of 91. Not only was he old enough to be her father, but he was old enough to be her grandfather, and maybe even her great-grandfather. Crystal is just 31 years old — that’s a 60-year different between the lovebirds. If you just imagine your grandfather having sex with someone who is 60 years his junior (sorry), you will see why we think these two more than deserve their spot on this list. Gag!
14. The Swastika Twins
Convicted mass murderer Charles Manson is 53 years older than his former fiancée, Afton Burton, a.k.a. “Star.” He is 82 and she is 29 (they are on the same level of creepiness as Hugh Hefner and Crystal Harris!). Star began writing to the killer as a teen and later moved across the country to be close to him. Manson was a cult ringleader who was convicted of killing seven people in 1969. Apparently, this was appealing to Star, so she uprooted her life for him. Her love for him went so far, she even tried to copy his forehead swastika on her own forehead. The two got engaged but were never married since the relationship became impossible to sustain due to things like his being in solitary confinement, where no visits, phone calls, or anything of the sort is allowed. There were also rumors that Star had only wanted to marry him to be able to use his corpse for profit once he passes. It is a twisted tale from every angle. We just take comfort in the fact that these two clowns never got the chance to actually be together intimately.
13. Maleficent And Goofy
Nowadays, Angelina Jolie is always associated with her ex-husband, Brad Pitt. Even though they have been divorced since 2016, they are still commonly referred to as “Brangelina.” But before Brad, Angie had been married twice. First, there was Jonny Lee Miller from 1996 to 1999. Her second husband was Robert “Billy Bob” Thornton, an actor known for Fargo, Bad Santa, Armageddon, and countless other movies and television shows. He is not exactly what we would traditionally think of as hot or even attractive. And let’s be honest, whoever would have thought that the world’s most beautiful woman — who is also a successful actress and humanitarian — would be with a dude named “Billy Bob?” And his looks are every bit as goofy as his name. The two made an odd pair, and they were married from 2000 to 2003. They split because, according to him, she made him feel inadequate. Basically, it is awkward to picture these two together, even though they were very much an item. Plus, they used to wear vials of each other’s blood around their necks. Freaky!
12. Most Messed-Up Couple, Ever
These two just scream “creepy.” From two different worlds, they met online — she is a 42-year-old mom of four from Sandusky, Ohio, and he is a 27-year-old attractive young man from Tunisia. The unlikely duo ended up marrying after a rocky 90 days, which was all documented on the TLC show 90 Day Fiancé. The awkwardness continued on the spin-off show 90 Day Fiancé: Happily Ever After? Mohamed had always been suspected of just using Danielle for a green card, but she also got called out for misleading him about her undisclosed finances, her criminal record, etc. And Mohammed exposed her for having an STD and a “smell” that “no man would want to have sex with.” It was pretty harsh, but he was no prize himself. It was never clear whether he truly was just using Danielle, but his relationships with other women did not help his case. Also, he has a creepy little mustache that looks like it belongs to a pubescent boy, and he is shady as hell. Together, the two made for some great entertainment, but they were a very cringe-worthy couple.
11. Teen Mom Almost Married This Huge Creeper
Amber Portwood first appeared on MTV on 16 and Pregnant when she gave birth to her daughter, Leah, in 2008. Since then, she has been on Teen Mom as one of the original girls. The show has followed her through her struggles with depression, mental illness, anger issues, custody disputes, drug addiction, prison time, and most recently, her controversial relationship with the much older Matt Baier. Matt is 18 years her senior, and a baby daddy to five (possibly more) kids, one of whom is a grown adult and was living with Amber and Matt. The two were engaged, but he is also an addict, has baby mama drama, and was constantly being accused of this and that by fans of the show who wanted Amber to ditch him. She did not trust him much, and in the end, they parted ways. It was probably for the best because he was always under scrutiny for having been a Teen Mom fan before meeting Amber, and for having tried to date her costars before her. All in all, he was pretty creepy, and although Amber has her issues too, they were bound to bring each other down.
10. Daughter Turned Bride
What is very bizarre about the relationship between Woody Allen and Soon-Yi Previn is that before they were husband and wife, they were father and daughter. Soon-Yi was his adopted daughter with his ex-partner, Mia Farrow. Thank God there is no blood relation, but still, that is pretty weird, and definitely far from normal. But the two have been married for 20 years, which is quite impressive, given the circumstances of course. She was adopted as a young child from an orphanage in South Korea. The famous director helped raise her and later married her. In an interview with Vanity Fair, Allen described how his wife really responded to and “blossomed under” his paternal influence. He said, “She deferred to me, and I was happy to give her an enormous amount of decision-making just as a gift and let her take charge of so many things. She flourished.” And let’s not forget Allen’s obsession with young Hollywood starlets like Scarlett Johansson. He definitely has a preference for much younger women, but in the case of he and Soon-Yi, their age difference is far from the only thing that makes them a disturbing couple.
9. The Satanist And The Jewish Girl
As a pretty, young, and successful actress, Evan Rachel Wood could probably have her pick of men. For all intents and purposes, she is quite a catch. So, it is somewhat surprising that she dated goth rock star Marilyn Manson for over two years, and was engaged to him for another seven months. They ultimately called it quits in 2010, and now Evan is engaged to Zach Villa, and is the mother of one. At the start of her relationship with Manson, Evan was 19 and he was 36. But the age gap was not the only thing that made them an odd pair; there was also the fact that he is a Satanist and she is Jewish. They are a strange couple, indeed, and even though Evan seems relatively normal, Manson is weird enough for the both of them. Especially now at 48 years old, the aging goth rock star and devil-worshipper is far from appealing in any sexual sense.
8. Hermit Hippie Twin And Her Old Hubby
The world-famous Olsen twins are all grown up now, and Mary-Kate is even settled down and married. Her husband is Olivier Sarkozy, whose brother Nicolas Sarkozy was once the President of France. He is a 48-year-old French businessman and banker, and when he married Mary-Kate in 2015, he not only made her a wife, but a stepmother to his two children, Julien and Margot. Perhaps the creepiest thing of all is when you see photos of the new family of four. Sarkozy towers over his wife and children, who all look the same age since Mary-Kate is so petite. Rather than a husband and father, he looks more like a single dad of three next to them. But his advanced age compared to Mary-Kate is just aspect that makes them a strange pair. There is also the fact that Mary-Kate is quite the oddball. After having been out of the spotlight for several years, she is somewhat of a recluse, and her looks and behavior have been likened to many things, like an alien, a hippie, a homeless bag lady, and so much more. It is definitely not the kind of person you would think a high-profile banker such as Olivier Sarkozy would settle down with.
7. Britney And Her Wannabe-Rapper Husband
Thank goodness these two have long been over with, because what a kooky pair they made! Britney, at the time, was plenty desirable and cute and successful, albeit she retained a little of her trashy side. Kevin Federline, her husband of two years, brought enough trashiness for the both of them. He was always being accused of using her for her money, and in the end, they split after having two sons and spending a total of more than three years as an couple. The wannabe rapper married Britney after having known her for just five months. Since then, he says he gets $20,000 a month in child support from Britney, which probably goes a long way in supporting their two sons, his two kids from a previous relationship, and his two kids with his current wife. He is a classless, six-time-baby-daddy user who is gag-worthy enough for the both of them (although she had her moments, too).
6. Party Partners In Crime
Gag me! By the time these two started dating in 2007, the world had already had enough of Lindsay Lohan without her gross relationship with Samantha Ronson being rubbed in our faces all the time. LiLo was out of control and a far cry from the cute, sweet little girl we first saw in The Parent Trap. She had such a bright future, and while she has been mildly successful, her drama, behavior, and attitude have worked against her. In 2007, at the age of 21, she began dating 30-year-old British DJ Samantha Ronson. The two partied a lot, but LiLo kept their relationship under wraps for quite awhile, until 2008 when she admitted publicly that she was involved in a “gay love affair” with a woman.
5. Kylie And Tyga’s Sibling Connection
Another celebrity relationship that made us gag was Kylie Jenner and Tyga. Why you ask? Well, Tyga, who is seven years older than Kylie and began dating her when she was 17, fathered a baby with Blac Chyna, who would later date Kylie’s older brother, Rob Kardashian. It is like some messed-up, sibling-lover switcheroo. At one time, siblings Kylie and Rob were dating two people who already had a child together. Now Rob has fathered a baby with Blac Chyna, too — meaning his kid and her first child by Tyga are siblings, and Kylie is the aunt to Tyga’s kid’s sibling. Tyga and Kylie were an item from 2014-2017, which is a significant amount of time when you are still a teenager like Kylie was. She is now pregnant with her first child, a girl, with her boyfriend, Travis Scott.
4. Rob + Blac = Dream (Somehow)
For all of the reasons that Rob Kardashian’s youngest sister Kylie Jenner is on this list, so is he. Just like Kylie, he dated someone who had a child with his sibling’s lover. That makes things so unnecessarily complicated. But there are other reasons Rob and Blac — who were dating and engaged for a little over a year — make the list that are wholly separate from Kylie and Tyga. For instance, they are not the most attractive pair. No, there is no insane age gap separating them or anything like that, but they just do not look great- individually or together. Thinking of them as a couple is not the most pleasant pictures. How on Earth they made such a cute baby (Dream Kardashian) is beyond us!
3. Scott Disick And Bella Thorne
And while were on the topic of Kardashians, here’s another one for you. There was a time when the world thought Scott Disick would be with longtime love Kourtney Kardashian forever. Admittedly, it would have been a happy Kardashian ending if the dad of three had stuck around, but also admittedly, we love the drama of his life and want it to continue. And it has! Last year, he dated actress Bella Thorne, who is 14 years younger than him and was only 19 at the time. He is not that old, but to date someone that young is creepy. On her behalf, we cringe and thank goodness that the relationship only lasted two months. However, in those two months, you know that they hooked up, and it is just yucky to think about. He is so much older, has lots of baggage and issues, and is a dad to little ones. I am sure in 15 years he would be grossed out if his daughter Penelope started dating an older scuzzy guy who is notorious for drinking, partying, and sleeping around with a much younger women. Just… ew.
2. This Quirky Duo
I gotta say, I love these two. They are hilarious and very talented. The actor/actress duo are faves of many people, but the fact that they are a funny-looking duo cannot be denied. And thus, as such, they earned their spot on this list. We got a little taste of the “sexier” side of Danny when he guest-starred on a 2004 episode of Friends as Roy the stripper, and it is not something we feel the need to see again. Ever. It’s also hard to stomach his gross persona in It’s Always Sunny in Philadelphia. Sadly, after more than 40 years together, the couple called it quits last year in a $140 million divorce. They were a quirky pair who could always bring a smile to your face, and thankfully, it seems they have been able to remain friends and keep up with their quirky ways. Just a few months ago, they were spotted dining out, and even flossing together at the table afterward!
1. Johnny’s Grunge Rubbed Off On Amber
You may not expect such a high-profile celebrity couple such as Johnny Depp and Amber Heard to be on a list like this, and yet, here they are. Maybe there was a time before when neither of them (including the grungy, dirty-looking Johnny) were thought of as “hot,” but as he’s gotten older, Johnny seems to keep getting weirder and weirder. His roles have always been unique (he played Edward Scissorhands, Captain Jack Sparrow, Whitey Bulger, the Mad Hatter, Sweeney Todd, Willy Wonka, etc.) and if anyone can appreciate a versatile actor, it’s us. But sometimes, based on his looks and behavior, it seems like he’s a quirky character in real life as well. And as for Amber, well she may be beautiful, but Johnny’s weirdness was rubbing off on her, which was very apparent in their 2016 dog-smuggling apology video that can only be described as bizarre.
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