Everyone knows you don't date your friend's ex.
But when your family hooks up with your ex, things get really weird.
From macking on siblings, to widows, to adopted daughters, these are the kind of real-life
forbidden romances only Hollywood could cook up.
Playboy magnate, Hugh Hefner, took cradle-robbing to a whole new level when he dated twin sisters
Karissa and Kristina Shannon at the same time.
In 2008, Hef found comfort in the then 19-year-old twins in the wake of his breakup from the
original Girls Next Door stars Holly Madison, Kendra Wilkinson, and Bridget Marquardt.
"Drinking with three blondes, I guess that's just a regular day for you."
"A slow one, yes."
The Shannon twins stepped into The Girls Next Door vacancy alongside Crystal Harris, who
Hef eventually wed, until his death in 2017.
According to Karissa, the twins found Hefner's first rule of the mansion a tad difficult
to follow.
She told The Sun,
"We were not allowed to have boys in the house…That was one of the main reasons we moved out.
But living there and being seen out with other guys, Hugh was tripping."
Hugh was nice enough to let them live in the guest house before eventually sending them
packing for good in 2010, after which Karissa confirmed to The Celebrity Cafe what everyone
had already speculated about this whole scandalous romance.
She said,
"It's a whole new life…I got TV shows, a lot of experience, and stuff like that.
I did a lot more covers for magazines.
I did a commercial for Guitar Hero.
There's just so much stuff and opportunities, it's just crazy."
In May 2015, Former Vice President Joe Biden's eldest son, Beau Biden, died tragically of
brain cancer.
But by March of 2017, Beau's younger brother, Hunter, confirmed that although he was still
married to his wife, Kathleen, he had begun a romantic relationship with Beau's widow,
Hallie.
And apparently the rest of the Biden clan was cool with this.
The former VEEP said in a statement via Page Six,
"We are all lucky that Hunter and Hallie found each other as they were putting their lives
together again after such sadness.
They have mine and Jill's full and complete support and we are happy for them."
"Worst thing that could have ever happened to me, happened, when Beau died."
But not everyone was excited about the new couple, least of all, Kathleen Biden, Hunter's
estranged wife.
In her divorce filing, Kathleen accused Hunter of infidelity, drug use, and squandering the
family's money on quote "his own travel [and] multiple hotel rooms on the same night, gifts
for other women, alcohol, strip clubs, or other personal indulgences".
"Isn't this something you want to get to the bottom of?"
"No, because I trust my son."
Hunter also suffered previous embarrassments when his name popped up on the leaked list
of Ashley Madison clients, though he denied ever using the site.
He was also dismissed from the Navy after testing positive for cocaine.
According to ABC, the couple broke up in 2019, before Biden married South African filmmaker
Melissa Cohen just six days after they met.
In one of the most convoluted love-triangles ever, Kylie Jenner and her half brother Rob
Kardashian have managed to turn their already reality-TV-famous brood into a spectacle of
a whole other sort.
They each dated one half of the formerly engaged couple Tyga & Blac Chyna, who also have a
son together.
"Here comes Kylie and Tyga, I kinda talked to them for a moment because this is gonna
be my future sister-in-law."
Tyga is an allegedly broke rapper who was on-again off-again with Kylie until around
2016.
Blac Chyna is a former stripper turned eyelash mogul who had a baby with Rob Kardashian,
and then promptly left him, according to TMZ.
Justin Bieber's association with the Kardashians started back in 2010 when he and Kim Kardashian
did their now infamous Graduate-themed photoshoot for Elle.
She was 29, and he was 16 at the time, so the tabloids had a field day, but Kim quickly
shot down any rumors of inappropriateness.
Kim also allegedly tried to set the Canadian crooner up with her sister, which would prove
to be something of a prophecy.
"I wanted to set him up with my sister Kendall who's 14.
He didn't wanna be hooked up with my sister, he liked me."
Cut to 2015, when Kourtney Kardashian finally moved on from her long-time boyfriend and
baby-daddy, Scott Disick, and allegedly set out to make him jealous by hooking up with
Bieber, according to Us Magazine.
Admittedly, we're dealing with 100% unsubstantiated rumors here, but in turn, Lord Disick shacked
up with Bieber's ex, Sofia Richie.
But hang on, because while the whole Justin-Kourtney drama was just picking up steam, Bieber was
spotted arriving separately to the same club as Kendall Jenner...Sound the hookup alarm!
Sadly, as far as this drama goes, Biebs is now a married man who probably doesn't care
about any of it.
Most of the dating drama involving Canadian rapper Drake has centered on his romance with
Rihanna.
The "are they or aren't they?"
between the duo has been raging since 2005, according to Vulture.
But this is about his former flame and Instagram model, Crystal Westbrooks, and the time she
publicly shaded her sister, fellow Instagram model, India Love, for hooking up with Drake.
Shady.
According to The Jasmine Brand, Crystal retracted her furious tweets, which accused her sis
of quote "hopping on her exes."
India never even confirmed their relationship, but because of Crystal's accusations and the
fact that India was constantly backstage at Drake's shows, people thought there was a
least a groupie thing happening.
"That's just not something I just talk about, so I'm just gonna keep it there."
Regardless of who did what with whom, no decent sister wants to be responsible for creating
that reputation, so Crystal quickly stepped up and tweeted,
"I reacted like an idiot to a story that I clearly knew nothing about nor was true.
So sorry baby girl, love u more than u love french fries."
Sooooo…did both sisters get down with the rapper, then agree to cover it up?
Only Drizzy knows for sure.
As soon as Bella Thorne shed her Disney persona, she almost immediately transitioned into a
social media celebrity by basically posting herself in a bikini every day to either Snapchat,
Instagram, or Twitter.
It's a guaranteed way to gain followers and has the added benefit of setting fire to any
lingering relationship with children's TV that you may have.
"Okay, but what I don't get is why exactly are you friends with me?"
In continuation of her image makeover, Bella completed the trifecta by simultaneously ditching
her long-term boyfriend, Gregg Sulkin, who also has Disney roots, revealing to her Twitter
followers that she's bi, and then posting photos of herself making out with her brother's
ex-girlfriend, Bella Pendergast while referring to her as her quote "soulmate" and "baby,"
according to Jezebel.
They were also spotted holding hands while going to a yoga class, but if they ever were
a real couple, it was short-lived.
Thorne quickly swapped her brother's ex for her own ex, Gregg Sulkin's good pal, Tyler
Posey, within a month, according to USA Today.
Trying to keep up?
Well, no worries, because Thorne ditched Posey a month later for Charlie Puth, who she's
currently no longer hooking up with either.
When basketball legend Magic Johnson's son, EJ Johnson, got his big break with his E!
reality show, EJNYC, he did not hesitate to drop a major bomb during the premiere episode.
In one scandalous scene, EJ confronts his sister, Elisa Johnson, about her new boyfriend,
a French model named Anthony.
"She literally could have picked up a garbage person off the side of the street, a crackhead,
I would have been fine.
Anything other than Anthony."
According to EJ, Anthony allegedly quote "led him on" one night at a club so that EJ and
his rich friends would treat him to VIP status.
EJ even alleges that he and Anthony kissed, but that somehow didn't faze Elisa one bit
who said, per the Daily Mail,
"My brother wants me to cut things off with Anthony, but I can't do that because I have
developed serious feelings for him."
So…Does Anthony deny any part of this story?
Because if he does, why would EJ have lied about that?
And if he doesn't deny it, is Elisa just cool with her boyfriend making out with random
dudes to get free drinks?
So many questions.
Romantic entanglements have probably caused fighting in bands since humans were banging
rocks together and dancing around a fire.
The Beatles and Fleetwood Mac, arguably two of the greatest of all time, weren't even
immune.
So what chance did a bubblegum pop outfit like The Jonas Brothers have, being infiltrated
by a hottie like model Gigi Hadid, who Nick and Joe both dated.
Fortunately, Gigi and Nick were never that serious, so it was no big deal when she and
Joe started hooking up.
So, while Gigi clearly had the potential to be the Yoko of the JoBros, that wasn't the
case at all.
Sorry, drama lovers!
It turned out, Nick couldn't have been more supportive of his big bro smoothing up on
his former flame.
He told E! News,
"I like them together.
It's a good thing.
Joe and I are best friends.
We're each other's, you know, sort of, support system and closest friends…"
Sounds legit, right?
Like…best friends are always cool with it when one of them starts swapping spit with
their ex.
Just ask Denise Richards and Heather Locklear.
Obviously, none of it matters now, because both Joe and Nick eventually married other
women, actresses Sophie Turner and Priyanka Chopra.
But it still begs the question: Did Gigi think Kevin was cute?
It always seemed like out of the Kardashian-Jenner kids, Caitlyn's lesser-known brood of Brody,
Brandon, Burt, and Cassandra Jenner were the more down-to-earth group of siblings.
But maybe that's just because they didn't get as much screen time, because on an episode
of The Brody Jenner & Dr. Mike Dow Podcast, Brody said he was his sister-in-law Leah's
boyfriend before she later married his brother, Brandon.
Alright, we should probably admit we're intentionally blowing this out of proportion, a little bit.
Leah was also a guest on the infamous podcast where she quickly clarified, via US Weekly,
"That is not true.
I met Brandon through Brody.
We went to school together when we were 11.
Okay, 11.
You don't kiss, you don't make out, you don't hold hands, you beat each other up, you play
basketball."
Brody then admitted to the exaggeration, and joked that he shot her with a BB gun.
Seriously, is it weirder to date the same girl as your brother, or to try to make people
believe you did, in a shameless effort to push an extra couple downloads of your podcast?
We're pretty sure we know the answer to that.
One last ironic twist to Brody's make-believe tale of shared sibling romance: His podcast
description claims to be a quote, "fresh take on relationship issues that young people face
today."
For what it's worth, both Brody and Brandon's marriages have ended since this whole thing.
Maybe when it comes to relationship advice: do what Brody says, not what Brody does.
"What I've learned is just to not expect too much."
This one is the mother of all family love triangles, because it dives directly into
the bizarro world of a father hooking up with his then-girlfriend, actress Mia Farrow's
adopted daughter, despite Soon-Yi's own protests to Time magazine that Woody was in no way
a quote "father or stepfather" to her.
Okay.
So that makes it not at all odd that in her early twenties, she began a relationship with
her mom's boyfriend who happened to be 35 years older than her, right?
"So much of what's filtered out about me over the years has been completely mythological.
And some of it's been true of course."
Oh, and about him not being a father or stepfather to her?
Woody has something to say about that.
In a rare 2015 NPR interview, the director spoke candidly about his relationship with
Soon-Yi, saying,
"I was paternal.
She responded to someone paternal.
I liked her youth and energy.
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.
It was just a good-luck thing."
Well so much for that quote "not at all like my dad" stuff.
But wait.
It actually somehow gets worse.
Woody went on to say,
"I started the relationship with her and I thought it would just be a fling, it wouldn't
be serious.
But it had a life of its own.
And I never thought it would be anything more."
Yikes.
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