29 Forgotten Celebrity Couples That Seem Like Unexpected Matches Now

A look back at some surprising celebrity romances that flew under the radar.

Published on Mar. 6, 2026

Got story updates? Submit your updates here. ›

It's impossible to keep track of all the pieces of celebrity gossip. Relationships form, enemies emerge, and before long, much of their drama quietly fades from public attention. But every now and then, you stumble upon an old photo or headline and wonder to yourself, 'Wait... These two? Really!?' This article puts together a list of famous couples that flew under many people's radars, from Macaulay Culkin and Mila Kunis to Madonna and Tupac.

Why it matters

This story provides a nostalgic look back at some surprising celebrity pairings that were once the talk of Hollywood but have since been largely forgotten. It serves as a reminder that even the most unexpected celebrity romances can capture the public's attention, at least for a time, before fading from the spotlight.

The details

The article covers 29 different celebrity couples, ranging from Macauley Culkin and Mila Kunis to Ryan Gosling and Sandra Bullock. It delves into the details of how these relationships started, how long they lasted, and what ultimately led to their demise. Some, like Culkin and Kunis, managed to keep their romance largely under the radar for years, while others, like Angelina Jolie and Billy Bob Thornton, were tabloid sensations.

  • In 2002, Janet Jackson and Matthew McConaughey went on a single dinner date.
  • Macaulay Culkin and Mila Kunis dated from 2002 to 2011.
  • Ryan Gosling and Sandra Bullock dated from 2001 to 2003.
  • Jennifer Garner and Scott Foley were married from 2000 to 2003.
  • Evan Rachel Wood and Marilyn Manson were engaged in 2010.

The players

Macaulay Culkin

An American actor who rose to fame as a child star in the Home Alone films.

Mila Kunis

An American actress known for her roles in That '70s Show and the Black Swan.

Ryan Gosling

A Canadian actor known for his roles in films like The Notebook and La La Land.

Sandra Bullock

An American actress known for her roles in movies like Speed and The Blind Side.

Janet Jackson

An American singer, songwriter, and actress, known as the "Queen of Pop".

Matthew McConaughey

An American actor known for his roles in films like Dallas Buyers Club and Interstellar.

Got photos? Submit your photos here. ›

What they’re saying

“We must not let individuals continue to damage private property in San Francisco.”

— Robert Jenkins, San Francisco resident (San Francisco Chronicle)

“Fifty years is such an accomplishment in San Francisco, especially with the way the city has changed over the years.”

— Gordon Edgar, grocery employee (Instagram)

What’s next

The judge in the case will decide on Tuesday whether or not to allow Walker Reed Quinn out on bail.

The takeaway

This case highlights growing concerns in the community about repeat offenders released on bail, raising questions about bail reform, public safety on SF streets, and if any special laws to govern autonomous vehicles in residential and commercial areas.