Hailey Watson
10 Hollywood Friendships That Survived Dating the Same Person
Hollywood is full of complicated love triangles and dramatic breakups, but some celebrity friendships are strong enough to survive even the most awkward situations.
When two friends date the same person, things could easily turn messy and ruin their bond forever.
However, these famous pairs prove that real friendship can overcome romantic history and jealousy, showing us that loyalty and understanding matter more than past relationships.
1. Courteney Cox and Jennifer Aniston
When Adam Duritz from Counting Crows dated both of these Friends stars, fans worried their real-life friendship might crumble.
Aniston had a quick romance with the musician back in 1995, while Cox started seeing him two years later in 1997.
But these two proved that sisterhood beats any boy drama.
Their bond from filming Friends together for ten years was way too strong to let a guy come between them.
Today, they’re still incredibly close, attending each other’s parties and supporting one another through life’s ups and downs.
Their friendship shows that when you truly care about someone, past relationships become just funny stories to laugh about later.
2. Selena Gomez and Miley Cyrus
Back in their Disney Channel days, both Gomez and Cyrus had crushes on Nick Jonas.
Cyrus dated him first in 2006, followed by Gomez’s turn in 2008 when they were all young teenagers navigating fame.
Growing up in the spotlight together created a special bond between these two stars.
They understood the pressure of being child celebrities better than anyone else could.
Even though they occasionally had rough patches in their friendship over the years, they always found their way back to each other.
Their story teaches us that childhood friendships can survive almost anything, including dating the same person during those confusing teenage years when everyone’s figuring out relationships.
3. Nikki Reed and Nina Dobrev
Reed married Ian Somerhalder in 2015, just a few years after he broke up with Dobrev, his Vampire Diaries co-star.
Fans immediately assumed drama and tension between the two women, creating rumors of a bitter feud.
However, Reed and Dobrev surprised everyone by becoming genuine friends.
They started posting photos together on social media, showing the world that women don’t have to be enemies over a man.
The trio even vacations together now, proving that maturity and respect can overcome any potentially awkward situation.
Their friendship reminds us not to believe gossip and shows that people can handle complicated relationships with grace, kindness, and understanding when everyone involved chooses peace over drama.
4. Taylor Swift and Gigi Hadid
Both of these superstars fell for Joe Jonas at different times in their lives.
Swift famously dated the Jonas Brothers singer in 2008 when they were both teenagers, while Hadid’s relationship with him happened seven years later in 2015.
Despite sharing romantic history with the same guy, Swift and Hadid became incredibly tight friends.
They’ve been spotted hanging out in New York City countless times, supporting each other at concerts and fashion shows.
Their friendship proves that timing matters more than who dated whom first.
When two people genuinely click as friends, they don’t let an ex-boyfriend create awkwardness or tension between them, especially when those relationships happened years apart.
5. Drew Barrymore and Kristen Wiig
Barrymore spent five years dating Fabrizio Moretti, the drummer from The Strokes, before their relationship ended in 2007.
Four years later, Wiig started her own romance with the same musician.
Instead of creating tension, Barrymore actually celebrated the new couple.
She publicly said it seemed perfect that Wiig and Moretti found each other, showing incredible maturity and kindness.
This friendship demonstrates that you can genuinely want your ex to be happy with someone else, especially when enough time has passed.
Barrymore’s supportive attitude proves that holding grudges or feeling territorial about past relationships only hurts yourself, while being generous and understanding creates positive energy for everyone involved in the situation.
6. Gwyneth Paltrow and Drew Barrymore
Luke Wilson dated Barrymore during the late 1990s before starting a relationship with Paltrow in 2001.
Both actresses had successful careers and moved in the same Hollywood circles, making things potentially uncomfortable.
Yet their friendship never suffered from sharing romantic history with Wilson.
They continued supporting each other’s projects and attending the same industry events without any weirdness.
Their bond shows that when friendships are built on mutual respect rather than competition, they can weather any storm.
Paltrow and Barrymore understood that Wilson’s romantic choices didn’t define their relationship with each other, proving that women supporting women is always more important than fighting over guys who clearly weren’t meant to be forever anyway.
7. Cameron Diaz and Kate Hudson
Baseball superstar Alex Rodriguez dated Hudson in 2009 and then moved on to Diaz the following year.
Media outlets immediately started reporting on a supposed feud between the two actresses, claiming they hated each other.
While things might have been tense initially, both women eventually moved past the awkwardness.
They’ve been photographed together at various Hollywood events, smiling and chatting like the drama never happened.
Their reconciliation proves that sometimes friendships need a little breathing room after romantic complications.
Hudson and Diaz show us that it’s okay to take time apart when things feel weird, but true connections can be rebuilt with forgiveness and understanding once everyone has moved forward.
8. Taylor Swift and Sophie Turner
Swift’s teenage relationship with Joe Jonas in 2008 became famous after she wrote songs about their breakup.
Over a decade later, Jonas married Turner in 2019, and they had two children together before divorcing in 2023.
During Jonas and Turner’s difficult split, Swift stepped up to support Turner emotionally.
The two were spotted hanging out in New York City, showing genuine care for each other despite the complicated history.
This friendship highlights how women can support each other through tough times, even when an ex-boyfriend connects them.
Swift and Turner prove that shared experiences with the same person can actually create understanding and empathy rather than competition or resentment between women.
9. Demi Moore and Mila Kunis
Moore was married to Ashton Kutcher for six years before their divorce in 2011.
Just a year later, Kutcher started dating Kunis, his former That ’70s Show co-star, eventually marrying her in 2015.
Despite the potentially awkward situation, Moore and Kunis have handled everything with remarkable grace.
They’ve both spoken positively about each other in interviews, refusing to create drama.
Their mature approach shows that you can respect your ex’s new partner without feeling threatened or bitter.
Moore and Kunis demonstrate that when everyone involved chooses kindness over jealousy, families can blend peacefully, especially when children are involved, creating healthy environments where everyone can thrive and move forward successfully.
10. Jennifer Lopez and Leah Remini
Both Lopez and Remini dated the same guy early in their careers, though the details remain relatively private compared to other celebrity love triangles.
What matters most is how their friendship survived the experience.
These two have been best friends for years, with Remini even serving as a bridesmaid at one of Lopez’s weddings.
They vacation together, support each other’s projects, and genuinely celebrate each other’s successes.
Their lasting bond proves that when friendship comes first, romantic history becomes insignificant.
Lopez and Remini show us that real friends stick together through everything, including the awkwardness of discovering you’ve dated the same person, because true friendship is rarer and more valuable than any romantic relationship could ever be.
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