What are some of the weirdest celebrity couples that surprised everyone?

Anna Wintour and Bill Nighy began their relationship reportedly in early 2023, surprising many as they had been friends for years before officially dating at the Met Gala, showcasing how connections can evolve into unexpected romantic relationships.

Carey Mulligan and Marcus Mumford's relationship began in college, and they surprisingly married in 2012 after they had dated as teenagers, illustrating how early bonds can sometimes lead to lasting partnerships years later.

Avril Lavigne and Mod Sun were once rumored to be in a relationship, surprising fans who had mostly associated Lavigne with rock star personas like Chad Kroeger; their unexpected pairing raises questions about how people from similar but distinct musical backgrounds connect.

In a twist that blended music genres, Madonna famously dated Dennis Rodman in the 1990s, highlighting how opposites attract in celebrity culture, reflecting complex personal chemistry despite public disbelief.

Zac Efron and Vanessa Hudgens's real-life romance mirrored their on-screen chemistry in "High School Musical," making the transition seem natural for fans, demonstrating how shared experiences in high-pressure environments like filming can foster romantic connections.

The relationship between Jennifer Aniston and Adam Duritz in the late 1990s surprised fans as they were very different celebrity types, bringing attention to the unpredictability of romantic chemistry across supposedly incompatible personalities.

Gwyneth Paltrow and Luke Wilson had a brief but unexpected relationship after meeting through friends, showcasing how mutual acquaintances can lead to surprising romantic entanglements, regardless of public perceptions.

Rumors of a fling between Tom Cruise and Cher in the 1980s sent shockwaves through Hollywood, illustrating that celebrity pairings often challenge conventional beliefs about compatibility in age and public personas.

Perhaps one of the most talked-about moments was between Benji Madden and Cameron Diaz, who surprisingly married just months after they began dating, leading to discussions about the fast pace of relationships in celebrity culture.

The romance between the two artists, Rosalia and Jeremy Allen White, in 2023 highlighted how creative synergy can contribute to unexpected pairings, illustrating how artists find common ground in their creative endeavors.

When shocking revelations emerged about Pete Davidson and Kim Kardashian's relationship, it raised eyebrows due to their stark personality differences; such dynamics often challenge societal norms about relationships.

In a match that puzzled many, Selena Gomez and Justin Bieber’s on-again/off-again romance showcased how complex emotions can intertwine in celebrity relationships, leading to ongoing public fascination.

The relationship between Machine Gun Kelly and Megan Fox introduced fans to a unique blend of punk aesthetic and Hollywood glamour, evidencing how different backgrounds in the entertainment industry can create unexpected partnerships.

The confirmed coupling of Robert Pattinson and Suki Waterhouse was surprising given Pattinson’s previous role in the "Twilight" franchise, symbolizing how personal evolution can lead to partnerships that defy initial typecasting.

The unexpected pairing of Ariana Grande and Dalton Gomez revealed how relationships can thrive away from the public eye, showcasing how everyday love connections can yield significant results outside of the celebrity spotlight.

The brief relationship between Justin Timberlake and Cameron Diaz showcased how friendships can sometimes bloom into romantic endeavors, reflecting a common pattern in celebrity circles—as both individuals were at peak fame during their time together.

Jennifer Lopez and Ben Affleck rekindling their romance after nearly two decades apart emphasizes how time can alter perceptions and feelings, leading to unexpected reunions that captivate public attention.

The unlikely union of stars like John Legend and Chrissy Teigen demonstrates how mutual interests in social issues and philanthropy can forge enduring connections, highlighting an important aspect of contemporary celebrity relationships.

The highly-publicized relationship between Khloé Kardashian and Tristan Thompson revealed how complexities of personal history can lead to tumultuous partnerships that both engage and confound public interest.

The pairing of Kourtney Kardashian and Travis Barker illustrates how long-standing friendships can morph into romantic relationships, suggesting a deeper level of compatibility that everyday couples might share, emphasizing the emotional safety of established bonds.