The Oscar winner and the starlet, who are expecting a child together, have a long history

By Jennifer Garcia
Updated April 13, 2011 07:40 AM
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Graham/Boot/Allstar/Globe; Mike Marsland/WireImage

They may have sent shock waves through Hollywood with news that they’re expecting a child, but Benicio del Toro and Kimberly Stewart have more of a history than most people think.

While the actor’s rep says the two are not currently a couple, “They’ve been involved for years,” a source tells PEOPLE. “But it’s always been on and off with them, and for a very long time.”

Their individual romantic histories have also played out differently. The Oscar winner, 44, has been notoriously private about his love life, while many of Stewart’s past relationships have been in the spotlight.

The 31-year-old model-actress and star of the British reality show Living with Kimberly Stewart has been engaged twice – to musician Cisco Adler and Laguna Beach alum Talan Torriero – but not married. After her split from Adler, she had her “Daddy’s little girl loves Cisco” tattoo altered to read, “Daddy’s little girl loves Disco.”

In 2008, she was linked to Jude Law after the two were photographed in a lip lock by a British tabloid.

Meanwhile, del Toro has remained one of Hollywood’s reigning bachelors. He dated actress Sara Foster in 2005 and has been linked with other young starlets, such as Lindsay Lohan and Scarlett Johansson.

But the Puerto Rico native hasn’t ruled out the possibility of settling down, telling Esquire in 2005, “I’d like to be a monogamist. I’d like to be.”

Odd Couple

The pair’s Hollywood circles rarely overlap. While Del Toro often hits hot spots like the Chateau Marmont, Stewart has led a quieter life out of the spotlight in recent years, losing the party-girl image she had when she was galavanting around L.A. with the likes of Paris Hilton and Jack Osbourne.

Del Toro’s mysterious demeanor might be what appeals to Stewart. “Make me laugh and you might be in. And never dance. I like guys who sit in the corner instead of seeking attention,” she told FHM in 2007.

While the actor’s rep says del Toro “very supportive” of Stewart during the pregnancy, don’t expect the two to be out shopping for baby together. “Kimberly makes it a point to keep her private life out of the public,” says the source. “She has been very focused on charity work.”