In all of Hollywood history, nothing has been more gripping to the entire world than
celebrity couples. Tinseltown has treated us to some absurd pairings, but we're dishing on some
downright cringe-worthy relationships. From Billy Bob and Angelina, to Chelsea and 50 Cent, here are
the most uncomfortable star-studded hook-ups. Between the vials of blood and their completely
over-the-top PDA, Billy Bob Thornton and Angelina Jolie had a knack for making
us all feel like we were somehow invading their private space. There was something about them
being so comfortable in their raunchiness that made the rest of the world look at them sideways.
"We kind of signed our life away to each other. Legally. And with blood."
Years after their divorce, Thornton divulged the nitty-gritty details regarding those blood-filled
vials to a room full of students at Loyola Marymount University, sharing in a chat,
"We were apart a lot because she's off making Tomb Raider and I'm making Monster's Ball. She
thought it would be interesting and romantic if we took a little razor blade and sliced our fingers,
smeared a little blood on these lockets and you wear it around
your neck just like you wear your son or daughter's baby hair in one."
When it comes to these two, romance is very much in the eye of the beholder.
This unlikely pair got together back in 1999, and while not much tea has been spilled about
the relationship, Robin Givens has gone on the record saying her time with Howard Stern was
definitely enjoyable. As Stern previously told Rolling Stone — and just about everyone else — he
isn't exactly the most gifted man when it comes to his private parts, once telling the outlet,
"I might be one of the smallest guys in the world. […] Who the f---'s going
to admit to something like that? And that's great radio.
Because it's someone being honest about their fears and emotions."
Regardless, Givens revealed that Stern was quite the gifted lover.
Claiming he was quote, "unbelievable," the actress plainly stated on Watch What Happens Live in 2019,
"Howard Stern was a magnificent lover."
Chelsea Handler admitted that she used her old talk show to meet men,
but when she linked up with 50 Cent after he made an appearance on Chelsea Lately in 2009,
all of us went... huh? While Handler wasn't vocal about the relationship as it was happening,
she later spilled the beans in 2013, telling Oprah,
"[His] persona is completely antithetical to who he is in
real life. It wasn't the most serious relationship. […] I just was like,
'I'm not gonna be dating someone who's first name is a number [forever].'"
"He's so cute and you wanna like, you know, hang from his neck."
But the relationship quickly turned sour. As it turned out,
Handler was set to interview singer Ciara, an ex of Fifty's, and the rapper thought he'd be
doing Handler a solid by informing her of Ciara's possible lingering feelings for him.
The move didn't sit well with Handler, who recalled on Howard Stern,
"I go, 'Why are you telling me this? This girl is coming on the show tomorrow,
and now I have to look at her and think you guys have some weird thing going on.'"
Handler cut Fifty loose soon after the incident. Any way you slice it, we couldn't have seen this
one coming. According to Glamour, rumors that actor Kate Beckinsale was dating SNL's Pete
Davidson first started swirling when they were caught leaving the Golden Globes together in 2019.
While nothing was immediately confirmed, Beckinsale became quite protective over
Davidson over the course of their relationship. The actress — who's also
20 years his senior — stepped in to defend Davidson against Instagram trolls, twice.
"If you have questions about a relationship with a big age difference, just ask Leonardo DiCaprio,
Jason Statham, Michael Douglas, Richard Gere, Jeff Goldblum, Scott Disick…"
Though the pair was frequently spotted together in early 2019, the fling seemingly reached a
crescendo when the couple attended a hockey game, and piled on the PDA as Queer Eye's
Antoni Porowski tried to pretend nothing was going on. But all the tongue action in the
world couldn't save this couple. And they were rumored to have broken up in April of 2019.
This is the so-called "entanglement" heard around the world. Jada Pinkett Smith stunned everyone
when she confessed on her show, Red Table Talk, that she had been in a relationship with August
Alsina while she was married to Will Smith. Rumors that Jada and Alsina were once an item
had been swirling for a while, bolstered by several references in Alsina's music.
"I actually sat down with Will and had a conversation. He gave me his blessing."
It all came to a head when Alsina spilled all the tea during an interview with Angela Yee
and claimed that Will gave him permission to start the relationship with his wife.
In an effort to get ahead of the media firestorm that soon ensued,
Jada took to her show to tell her side of the story.
"What did you do, Jada?"
"As time went on, I got into a different kind of entanglement with August."
While most people might have been okay with the pair having a fling because, at the time,
the Smiths had separated, the circumstances under which Jada
and Alsina got together made the affair controversial. Jada said Alsina originally
got close to the family while he was going through some personal issues.
As the Smiths' relationship seemingly began to devolve, Jada turned to Alsina to numb the pain.
Keeping in theme with May to December relationships,
David Foster and Katharine McPhee have a 35-year-age difference between them.
What's even more awkward, is that his oldest daughter, Allison, is 14 years older than McPhee.
"I think it's so amusing that people are amused by my love life."
Foster and McPhee met back in 2006 when the Grammy-award winning music producer served
as a mentor on season five of American Idol. While the pair didn't immediately start dating,
they remained in each other's lives ever since. Foster told USA Today in 2020,
"I've known [Katharine] for 15 years. […] It was a comfortable transition, and it's a credit to both
my wife and daughters that they've just rolled with it and they do great together. It's been
years now with no animosity and no problems, and I have no reason to believe that'll change at all."
The two got hitched in 2019 and welcomed their first child, a son, in February 2021.
Rob Kardashian + the Kim lookalike The Kardashians certainly know how to
put on a show. But every once in a while, they do or say things that just seem
a wee bit too much. Cue Rob Kardashian's hookup with a Kim Kardashian lookalike.
In a 2017 episode of Keeping Up With the Kardashians,
Rob and sister Khloe were just hanging out, when their conversation took a turn, with Khloe asking,
“Do you remember when you f----- the girl who won the Kim Kardashian lookalike contest?"
Later on in the convo, Khloe went on to question why her brother never sought to
hook up with a Khloe Kardashian lookalike. We hope the ratings were worth it.
Proving that nothing is out of reach as long as you really believe in yourself,
one lucky fan dated former Wizards of Waverly Place star Jake T.
Austin after she persistently messaged him on Twitter for years.
According to People, Danielle Ceasar spent seven years chasing after the actor before
he finally took notice. The pair met at an event in 2011, but didn't become official until 2016,
when Austin posted a since-deleted shot of the two getting cozy. He told People at the time,
"We're young and having fun just getting to know each other.
It doesn't matter how you meet someone — on set, in a coffee shop, at school or in the business.
Sometimes you connect with people at the right moment and you just click.”
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