Couldn’t keep your eyes off Kylie Jenner and Timothée Chalamet at the Oscars 2025? Here are some of Hollywood’s most unexpected couples

Blackpink’s Lisa and Frédéric Arnault is a relationship that very few saw coming. K-pop stars have rarely ever dated those who aren't fellow K-pop stars, after all. 

However, the union between Lisa—a talented dancer, rapper and actress—and Arnault, the CEO of LVMH Watches, who is also the son of LVMH CEO Bernard Arnault—quickly established them as one of the most glamorous pairs in today’s entertainment landscape. Together, they’re seen as a power couple who bridged the worlds of entertainment, luxury and fashion.

Tom Cruise and Cher’s brief romance in the 1980s became a captivating footnote in Hollywood’s rich history of tantalising pairings.

Their relationship was marked by a significant age gap—Cher was 39 while Tom Cruise was 25—and contrasting public personas. Cher has always embraced a flamboyant, bold public identity, whereas Cruise is known for his intense and serious image. This striking difference between them captivated audiences, offering a glimpse into the fascinating dynamics of love and fame in Hollywood.

Hyuna and Dawn’s romance was an unexpected one—mostly because they broke norms within the typically conservative K-pop landscape. When they publicly announced their relationship in 2018, without the prior knowledge of their representative Cube Entertainment, the firm terminated both artists’ contracts, citing that they could not “maintain trust” with the couple; the news made international headlines. 

The two were not only dating but also made music together—something that not only showcased their talent but also redefined how love can thrive in the demanding realm of K-pop. While they officially ended their relationship in 2023, fans continued to support them for their expressions of authenticity 

Kim Kardashian and Pete Davidson’s whirlwind romance captured media attention due to their contrasting public personas—Kardashian’s polished image versus Davidson’s comedic, down-to-earth vibe.

Their playful chemistry, often showcased through social media and public events, turned heads and reignited conversations about love in the digital age. Despite the eventual end of their relationship, the couple’s unique connection resonated with many.

Brenda Song and Macaulay Culkin’s enduring relationship points to love blossoming from shared experiences in childhood stardom.

The actors, who both found fame at a young age and began dating in 2017, have navigated the challenges of the entertainment industry and emerged stronger together. Their bond, characterised by mutual support and camaraderie, continues to inspire fans, demonstrating that genuine connections can thrive, even in the chaotic world of celebrity.

Comedians Bill Hader and Ali Wong definitely deserve their place on this list, despite both working in the same field. 

There is a marked contrast between their comedic styles and personas: Hader is known for his deadpan humour, while Wong’s famed for her bold, expressive on-stage persona. 

Timothée Chalamet and Kylie Jenner’s romance caught many off guard, mostly thanks to the differences in their backgrounds. Chalamet is celebrated for his acclaimed roles in indie films and among the Hollywood artistic elite, while Jenner is a mogul in the realm of reality television and beauty, deeply embedded in the glamorous side of celebrity culture. 

Despite these contrasts, romantic moments between the two at the events they attend together often make headlines—whether at the Oscars 2025 or elsewhere—a show of their undeniable chemistry.

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