63119, NEW YORK, NEW YORK – Thursday June 23, 2011. Diane Kruger dazzles in a red gown at the amfAR Inspiration gala held at the Pavillion Gabriel in Paris.

Shia said his one date with Hilary Duff was definitely not worth repeating, describing it as “probably the worst date either of us have ever had.”

In his tell-all interview in DETAILS, Shia said he has undeniable chemistry with his Transformers co-star, Megan Fox, even though she was with Brian Austin Green! “It was what it was,” he said.

Shia has admitted to “philandering around” with his Transformers 2 co-star, Isabel Lucas, despite her being in a relationship with Adrien Grenier at the time!

British actress and Shia's Wall Street: Money Never Sleeps co-star, Carey Mulligan, was arguably his most serious girlfriend. After being introduced by their director, Oliver Stone, the couple dated from August 2009 to October 2010. Unlike his other ladies, Shia has never spoken badly about Carey and has said he respects her as an individual and as an actress.

Shia's most recent girlfriend, Karolyn Pho, isn't an A-list Hollywood actress or model — she's a stylist! “It's a pretty mundane, domestic, docile, lame, sort of not-that-exciting existence,” he said of the seven month relationship.

Nearly four years ago, Shia and then 19-year-old Rihanna were spotted on a date in Beverly Hills. Unfortunately for Shia, the date didn't pan out as well as he'd hoped. “It never got beyond one date,” he said in 2009. “The spark wasn't there. We weren't passionate about each other in that way, so we remain friends.”

Although it was never confirmed Shia and his Transformers: Dark of the Moon co-star, Rosie Huntington-Whiteley, actually hooked up, it was widely reported the actor has a major crush on the Victoria's Secret model and was trying to charm her during their shoot.

63119, NEW YORK, NEW YORK – Thursday June 23, 2011. Diane Kruger dazzles in a red gown at the amfAR Inspiration gala held at the Pavillion Gabriel in Paris.

Shia said his one date with Hilary Duff was definitely not worth repeating, describing it as “probably the worst date either of us have ever had.”

In his tell-all interview in DETAILS, Shia said he has undeniable chemistry with his Transformers co-star, Megan Fox, even though she was with Brian Austin Green! “It was what it was,” he said.

Shia has admitted to “philandering around” with his Transformers 2 co-star, Isabel Lucas, despite her being in a relationship with Adrien Grenier at the time!

British actress and Shia's Wall Street: Money Never Sleeps co-star, Carey Mulligan, was arguably his most serious girlfriend. After being introduced by their director, Oliver Stone, the couple dated from August 2009 to October 2010. Unlike his other ladies, Shia has never spoken badly about Carey and has said he respects her as an individual and as an actress.

Shia's most recent girlfriend, Karolyn Pho, isn't an A-list Hollywood actress or model — she's a stylist! “It's a pretty mundane, domestic, docile, lame, sort of not-that-exciting existence,” he said of the seven month relationship.

Nearly four years ago, Shia and then 19-year-old Rihanna were spotted on a date in Beverly Hills. Unfortunately for Shia, the date didn't pan out as well as he'd hoped. “It never got beyond one date,” he said in 2009. “The spark wasn't there. We weren't passionate about each other in that way, so we remain friends.”

Although it was never confirmed Shia and his Transformers: Dark of the Moon co-star, Rosie Huntington-Whiteley, actually hooked up, it was widely reported the actor has a major crush on the Victoria's Secret model and was trying to charm her during their shoot.