12 Celebrities Who Dated Their Co-Star’s Sibling

12 Celebrities Who Dated Their Co-Star’s Sibling

Hollywood is a small world, and when you mix family ties, co-star chemistry, and a dash of red-carpet allure, things get even more tangled. It’s not just celebrities dating each other—it’s celebrities dating their co-star’s siblings, which adds a whole new layer of intrigue. Imagine going to work, filming scenes with someone, and then realizing your co-star’s brother or sister is now your significant other.

1. Jake Gyllenhaal & Kirsten Dunst

Back in the early 2000s, Jake Gyllenhaal and Kirsten Dunst were one of Hollywood’s favorite young couples. Their relationship began not long after Kirsten starred alongside Jake’s sister, Maggie Gyllenhaal, in Mona Lisa Smile.

It was the kind of romance that made tabloids swoon: two good-looking actors from respected film families stepping out together.

While the pair eventually split after two years, their connection is still remembered as one of those classic “young Hollywood” romances. What makes it even juicier is imagining Kirsten filming scenes with Maggie while she was dating Jake off-screen.

Family dynamics must have been interesting, to say the least, but hey—that’s Hollywood for you.

2. Chris Evans & Jenny Slate

Everyone remembers when Captain America himself, Chris Evans, dated comedian Jenny Slate. But here’s the twist—Jenny once co-starred with Chris’s brother, Scott Evans, who carved out his own acting career in TV shows like One Life to Live.

That little Hollywood triangle made the relationship even more fun to follow. Chris and Jenny had a quirky, lovable romance that fans adored, even though it was short-lived. Their chemistry was obvious, both on the red carpet and in interviews.

While it didn’t last, the connection between Jenny and Scott gave their love story a kind of “small world” feel. Hollywood really does make the dating pool feel like one giant family reunion sometimes.

3. Cameron Diaz & Jared Leto

When Cameron Diaz and Jared Leto dated in the late ‘90s and early 2000s, it was a big deal—two A-listers at the top of their careers.

What made their pairing extra fascinating is that Jared’s brother, Shannon Leto, often crossed paths with Cameron through music and film events. Shannon was heavily involved with Jared’s band Thirty Seconds to Mars, which meant Cameron was never far from the family circle.

Their relationship reportedly lasted around four years, which is practically a lifetime in Hollywood terms.

Even though they didn’t end up together, their connection highlighted how dating one person in Hollywood often means you’re also connected to their siblings, friends, and entire professional network.

4. Robert Pattinson & Suki Waterhouse

Robert Pattinson and Suki Waterhouse have become one of Hollywood’s more private yet enduring couples. But the behind-the-scenes connection comes from Suki’s creative circles overlapping with Robert’s sister, Lizzy Pattinson, who has her own career as a singer and even contributed music to the Twilight films.

That shared artistic background gave their romance a unique “family ties” angle. While Robert is best known for his moody Twilight days, his relationship with Suki has shown a softer, more grounded side of him. The fact that Suki shares some professional overlap with his sister adds an interesting layer to their romance.

It’s almost like the Pattinsons were destined to keep their world wrapped in music, film, and love stories.

5. Zooey Deschanel & Jason Schwartzman

The quirky queen of indie rom-coms, Zooey Deschanel, once dated Jason Schwartzman, long before either of them settled down.

What ties this relationship to the theme is that Jason has co-starred in films connected with Zooey’s sister, Emily Deschanel, best known for Bones. Hollywood circles often blur the lines between personal and professional, and this was one of those cases.

Zooey and Jason’s relationship didn’t stand the test of time, but it’s remembered fondly as one of those perfectly “indie couple” pairings. With their artsy vibes and musical talents, it almost felt like a match made in Wes Anderson’s universe.

Still, fans got a kick out of the fact that Emily and Jason had their own on-screen connections while Zooey was dating him off-screen.

6. Jennifer Lawrence & Nicholas Hoult

Jennifer Lawrence and Nicholas Hoult’s romance began on the set of X-Men: First Class.

While the two had undeniable chemistry, there’s an added twist: Nicholas had ties to Jennifer’s brother, Blaine, through behind-the-scenes projects and personal circles. That made the relationship more layered than just your average co-star romance.

Their on-again, off-again relationship spanned several years and multiple X-Men films. Fans were always rooting for them, hoping the Hollywood pressures wouldn’t get in the way.

While they eventually called it quits, their relationship serves as a great example of how dating in Hollywood often involves siblings, co-stars, and a whole web of connections you’d never expect.

7. Adam Brody & Leighton Meester

Long before they became the ultimate “TV royalty” couple, Adam Brody and Leighton Meester were linked through their professional connections.

Adam’s breakout role on The O.C. meant his circle overlapped with actors who had ties to Leighton’s family, particularly through her sibling’s connections in the entertainment world.

When Adam and Leighton finally got together, fans of teen dramas everywhere celebrated. Seth Cohen dating Blair Waldorf? That was the ultimate crossover dream.

Now married with kids, they’re one of the rare Hollywood couples who’ve gone the distance. The fact that their relationship ties back into family connections only makes their story more Hollywood-perfect.

8. Macaulay Culkin & Mila Kunis

Macaulay Culkin and Mila Kunis dated for nearly a decade, making them one of the longer-lasting young Hollywood couples.

What tied them into this theme was Mila’s eventual on-screen collaborations with Macaulay’s brother, Kieran Culkin, who went on to star in Succession and several indie films.

The Culkin family is practically a dynasty in entertainment, and Mila found herself firmly in the middle of it during her relationship with Macaulay.

Though they eventually broke up, the connection between her and Kieran’s projects kept the family link alive. It’s one of those cases where dating one sibling almost guarantees that you’ll see the others on screen, too.

9. Liam Hemsworth & Miley Cyrus

The Miley Cyrus and Liam Hemsworth romance saga is practically legendary at this point. What makes it fit here is that Miley often crossed paths with Liam’s brothers, Chris and Luke Hemsworth, both of whom have their own Hollywood careers.

In particular, Miley was frequently spotted at events with Chris, who co-starred with many of her own industry friends.

Their on-again, off-again relationship kept fans on their toes for nearly a decade, ending in a short-lived marriage. While things didn’t work out romantically, Miley’s connections with the Hemsworth brothers gave the relationship a fun sibling overlap.

Imagine casually running into Thor at your in-laws’ dinner table—that’s not something most of us can say.

10. Julia Roberts & Lyle Lovett

When Julia Roberts shocked everyone by marrying country singer Lyle Lovett in 1993, the press couldn’t get enough. What tied it into this theme was Julia’s brother, Eric Roberts, who often moved in the same professional circles as Lyle.

The marriage may have been short-lived, but it certainly gave Hollywood some memorable family crossovers.

Although the marriage ended after just two years, Julia and Lyle’s whirlwind romance remains one of the most surprising pairings of the ‘90s. With her brother’s career colliding with their relationship, it made for an even richer Hollywood tale.

The Roberts family was already big in the acting world, and Lyle’s music career only added to the star power.

11. Brad Pitt & Juliette Lewis

Brad Pitt and Juliette Lewis dated in the early ‘90s, back when Brad was just on the verge of superstardom. Juliette’s brother, Lightfield Lewis, had acting connections that overlapped with Brad’s career, particularly through films like Kalifornia.

That made their relationship more than just a fling—it was another Hollywood family web in action.

Though their romance fizzled out, Brad and Juliette’s pairing is often remembered as one of his most “grunge-era” relationships. They embodied that cool, edgy early-’90s vibe.

And with the added connection of Juliette’s sibling being in the acting world, it was another example of how Hollywood is basically one extended family tree.

12. Katie Holmes & Joshua Jackson

During their Dawson’s Creek days, Katie Holmes and Joshua Jackson were teen heartthrob royalty. What makes their relationship land here is Joshua’s brother, Luke Jackson, who was involved in projects that intersected with Katie’s early career path.

Although their teenage relationship didn’t last, fans still look back fondly on Katie and Joshua as one of the sweetest young couples in TV history.

The fact that it also tied into Joshua’s family makes it even more of a classic “Hollywood (and TV) sibling connection” story. Sometimes those early romances set the tone for how fans see actors for the rest of their careers.