From Kendall Jenner To Demi Lovato: 9 Celebs Who Have Dated Their Famous Mates' Siblings

It’s always an awkward situation when you and your bestie have a guy in common. It’s uncomfortable enough when it’s an ex you both share, but it can be even tougher when your mate has decided to fall for your fam. You can feel trapped in the middle or just weird that they are not the right fit.

Sounds like something out of an actual nightmare? Then you will probs feel for these celebs...

BUT FIRST, CHECK OUT THE CELEBS WHO DARED TO DATE A CIVILIAN...

1. Kourtney Kardashian

Oldest Kardashian sister Kourt was rumoured to be hooking up with Justin Bieber, who is famously super close to her younger sissys Kendall and Kylie Jenner. Neither of them ever admitted the relationship publicly but that didn’t stop Scott Disick getting peeeeeved. Thankfully the youngest sisters didn't seem to care. 

2. Kendall Jenner

The world was shocked when it was reported that Kenny and Anwar Hadid, her BFFs Gigi and Bella Hadid’s younger brother, were spotted smooching on a date. It quickly came out that he had broken up with actress Nicola Peltz and she had unfollowed the entire Hadid clan on social media.

3. Blac Chyna

Kim’s pal Blac Chyna was tight AF with the Kardashian family long before the whole Tyga/Kylie Jenner/Chyna/Rob Kardashian super awkward love square. But when she started bashing Ky it all went south until she started dating her ex-BFF Kim’s brother Rob. And tbh it all got super complicated after that.

4. Chloe Sims

After a disastrous date with Ex on the Beach’s Dean Ralph, Chloe quickly fell into the arms of her friend Yasmin Oukhellou’s brother Adam Oukhellou and the pair have been well loved up ever since. TOWIE fans saw the women have a chat about the new couple and Yasmin give Chloe her blessing.

5. Gaz Beadle

When Marnie first entered the Geordie Shore house in series seven, her cousin Sophie Kasaei was beyond shocked. Her surprise continued when it came out that Marnie and fellow roommate Gaz Beadle had a flirtation before Marns arrived. Cue the pair hooking up and drama ensuing. 

6. Malika Haqq

It got very awkward for Khloe Kardashian when her BFF Malika fell for her little brother Rob Kardashian. It was all the more uncomfortable when it appeared the Rob was playing it super hot and cold with her resulting in Malika crying to Koko about it. Yikes.

7. Cheryl Tweedy

It’s thought that at the very start of Girls Aloud, Chezza was dating her BFF and bandmate Kimberly Walsh’s little brother Adam Walsh. But the pair split due to her busy schedule. She said in 2003: “He’s like the male version of me and we’re getting along just fine. Although he’s living in Yorkshire and I’m always on the road, it hasn’t been too much of a nightmare to see him.”

8. Stanley Tucci

The Devil Wears Prada besties Stanley and Emily Blunt not only share a fear of Miranda Priestly but also a family member. Emily introduced Stanley to her sister Felicity Blunt a few years after the pair filmed the hit movie, and the pair wed in 2012. Beyond cute.

9. Demi Lovato

We’re obsessed with Demi and Nick Jonas’ friendship tbh but it must have been kindaaaa weird when Demi started dating his brother Joe Jonas on the set of Camp Rock. Nick admitted he’d felt caught in the middle of their relationship, years later in 2016: “For a couple of years there was the Joe and Demi romantic thing, so I’d be this emotional bridge for them.”

And now, take a gander at the awkward AF moments when celeb exes came face to face...