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Celebrity

13 Seriously Sketchy Celebrity Relationships

May 4, 2015 by Andriena Baldwin
shefinds | Celebrity
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Hollywood is where anything can happen. And when it comes to stars and their dating lives, things are no different. There are couples who seem made for each other (eh, em Will Smithand Jada Pinkett). Then there are the ones we look at and say, "Now, how on Earth did these 2 get together?" From extreme age differences to being related, check out our list of relationships, past and present, that have us puzzled. [Photos: Splash News]
Kylie and Tyga at a glamorous event together

Between the age drama and the baby-mama drama, we can't say we're saddened by the recent rumors of Kylie Jenner and Tyga breaking off whatever it was they had going on. 17-year-old Kylie finally had enough after Blac Chyna, Tyga's ex and baby mama, posted photos of his text messages to her, claiming the rapper wants to get back together. Drama, drama, drama!

Courtney Love showcasing her signature style

Doug Hutchinson and Courtney Stodden have some sort of thing. Calling it a relationship just creeps us out.

Michael Lohan and Kate Major at a red carpet event

Michael Lohan and former tabloid reporter Kate Major tied the knot in 2014 (after many break-ups and make-ups). Besides the 23-year age difference, their extremely volatile relationship was documented on the fifth season of VH1's Celebrity Rehab, where all couples should sort out their issues...

Happy couple enjoying a romantic moment

Super cougar Sam Taylor Wood snagged up young hottie Aaron Johnson. What's a 24-year age difference other than a 24-year age difference, anyway?

Hugh Hefner with Crystal Harris at a party

There is a 60-year age gap between Hugh Heffner and his current wife, 29-year-old Crystal Harris. Enough said.

Linda Hogan and Charlie Hill posing together

Linda Hogan began dating Charlie Hill when he was just 19-years-old (she was 48). The couple is no longer together, and Charlie is now suing Linda for $1.5 million for treating him like a "day laborer," according to TMZ.

Mary-Kate Olsen at a fashion event

Mary-Kate Olsen and Olivier Sarkozy look like father and daughter. Need we say more?

Woody Allen and Soon-Yi Previn at an award show

Most people are pretty creeped out by the fact that Woody Allen broke-up with Mia Farrow to date her adopted daughter, Soon-Yi Previn. They also started dating when she was only 19 and he was 56.

Angelina Jolie and Billy Bob Thornton at a premiere

No one really knew what to think about Angelina Jolie and Billy Bob Thornton. But we were kind of disgusted by it.

Marilyn Monroe in a classic beauty pose

To be honest, anyone would create a weird pair with Marilyn Manson, but Evan Rachel Wood made it even more of an oddity.

Bradley Cooper at a film festival premiere

Bradley Cooper is hot, and Suki Waterhouse is young (23 to be exact). So when you think about Bradley being 40, and old enough to have been her father, things get a little weird.

Shaquille O'Neal showing off his signature smile

When Shaquille O'Neal started dating Hoopz, not only was there a gigantic gap in their age, but there was an even bigger one in their size.

Ashton Kutcher at a celebrity event

At first we thought it was a publicity stunt. But once Demi Moore and Ashton Kutcher convinced us it was love, they broke up.

 

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celebrity

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Andriena Baldwin has covered fashion, beauty, celebrity and more for SheFinds.com.

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Madonna showcasing her fashion at the Met Gala.
Taylor Swift boarding her private jet in 2024.
Jennifer Lopez flaunts bold fashion at American Music Awards.
Vittoria Ceretti and Leonardo DiCaprio at fashion event.
Emma Stone at the Annual Actor Awards ceremony.
Salma Hayek at the 12th Annual Breakthrough Prize Ceremony.
Kate Middleton during a state visit.
Ariana Grande at the Golden Globes red carpet.
Kylie Jenner in tailored black outfit at Met Gala 2025.
Taylor Swift and Travis Kelce spotted together.
Ivanka Trump and Jared Kushner at public event.
Brad Pitt and Ines de Ramon at F1 movie premiere.
Bad Bunny performing at the Grammys.
Angelina Jolie receiving the Trophee Chopard Award.
Selena Gomez at Rare Impact Fund Benefit event.
Brad Pitt and Ines de Ramon at F1 World Premiere.
Queen Camilla with Prince Harry and Meghan Markle
Travis Kelce and Taylor Swift enjoying a moment
Barack Obama and family at a public event
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