40+ Celebs With Amazing Dating Histories, Ranked

Published on 09/22/2023
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Charlize Theron

Throughout her career, Charlize Theron has astounded audiences. She’s ready to take the lead in anything from action to serious parts. Between 1995 and 1997, Theron was with Craig Phillip Bierko and then with Stephan Jenkins from 1998 to 2001.

Charlize Theron

Charlize Theron

Despite this, she was still romantically involved with George Clooney in 2000. She was married to Stuart Townsend (above) from 2001 until 2010 and subsequently to Keanu Reeves. Following a few more speculations, she quickly dated Alexander Skarsgard and Eric Stonestreet.

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Sandra Bullock

Sandra Bullock was first photographed dating Michael Mailer in 1989. Bullock dated Love Potion No. 9 co-star Tate Donovan between 1992 and 1995. She then dated Troy Aikman and Matthew McConaughey, and there were rumors that she was dating Keanu Reeves.

Sandra Bullock

Sandra Bullock

Following her breakup with McConaughey, the actress dated Dweezil Zappa, Bob Schneider, Hugh Grant, and Ryan Gosling and eventually married Jesse James. She dated Ryan Reynolds, Chris Evans, and then Bryan Randall after they separated.

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