Famous flings: 10 fantasy celeb hook-ups

Jul 20, 2010 at 8:00 a.m. ET

Playing matchmaker can be fun.  Who doesn't love pretending to be cupid and setting up potentially compatible friends and coworkers in hopes of a love connection?  We've decided to take our set-up skills to Hollywood and make some imaginary match-ups with some of our favorite stars.  Read on for our fantasy dating pool and see if you agree with our celebrity couplings.

10Leo and Kate WinsletKate Winslet and Leonardo DiCaprio

Anyone who's seen Titanic (and let's face it, who hasn't?) has probably wished for these two to become an off-screen couple. The film that turned Winslet and DiCaprio into megastars also bonded them for life. But now that Kate is single, it would be very satisfying to see friendship blossom into romance.

9Jennifer Aniston and John Stamos

After her devastating break-up with Brad Pitt, Jennifer Aniston hasn't been able to catch a romantic break. She's dated musicians and movie stars without any luck, so maybe it's time to turn to television. John Stamos maintains a low profile, but still continues to act, be it on stage or the small screen, and he seems like he'd give Aniston some stability, rather than talking about her to various publications (we're looking at you, John Mayer). Plus they'd look great together, which is a big plus.

8Anne Hathaway and Jake Gyllenhaal

Someone else who's had poor luck in the dating department, Anne Hathaway needs a nice guy for once and we're suggesting Jake Gyllenhaal. Not only would these two look adorable together, we think they'd click on an intellectual level as well. They both choose interesting films, with well-written dialogue and seem like they'd be professional on set as well as off. And we know from recent interviews promoting Price of Persia that Gyllenhaal is a funny (as well as sexy) guy – the perfect combination for someone who's been dealt a bad hand in the boyfriend department so far.

7Ryan Gosling and Michelle WilliamsRyan Gosling and Michelle Williams

Though there have been a few rumours floating around about a possible hook-up at Cannes, these two have yet to get into a romantic collision. But we think they should. Not only are they both gorgeous, they're great actors (seen together most recently in Blue Valentine) who seem much more mature than their Hollywood peers. We can picture these two huddled together in artsy cafes, or walking hand in hand down a cobblestone street somewhere in Europe. This would be one smart and sexy pairing.

6James Franco and Natalie Portman

Seeing these two smarty pants together would be a love match on a higher level. Both see themselves as artists rather than simply, entertainers, and you can't deny the potential for chemistry. Both have an air of mystery and eyes that seem to see more than just what's on the surface.

Up next: The Top 5 fantasy celeb hook-ups >>

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