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Playing matchmaker for Pippa Middleton

Jessica Padykula is a freelance writer and editor in Toronto, Canada covering a wide range of topics for several online lifestyle publications. She is a regular contributor for SheKnows, covering travel, style, relationships, health and ...

Setting up Pippa

She may not have married a prince but Pippa Middleton has been receiving almost as much attention as her older, more officially royal sibling. All eyes are on the brunette stunner as she goes about her life and as far as we can tell, she's made for the spotlight. The camera loves her – and by the looks of things, she loves the camera. Despite the fact she's attached, we think it would be fun to set her up with some of Hollywood's most eligible bachelors. Check out our top picks.

Setting up Pippa

Setting up Pippa

Jude Law

Now that Jude and Sienna are done (again), Law is in the clear to court pretty Pippa. We think his cavalier demeanor and British charm would be a fabulous love match for this Middleton sister. He also seems to know how to show his lady loves a great time (when they were happy, he and Sienna definitely knew how to have fun). He's suave, swanky, debonair and could surely do a good job sweeping Pippa off her feet – at least until the next sexy suitor comes along.

Photo Credit:

Setting up Pippa

Prince Harry

What's the problem? Too obvious? In our defense, we just can't help ourselves – it would be too perfect for both princes to be with Middleton sisters, which is why it would likely never happen, but we can still picture these two together – double dating with the Duke and Dutchess of Cambridge. We really do think this handsome prince would be a really romantic match for the winsome and sophisticated Pippa – we can see him doting on her and the two of them jetting off to party in some of the world's hippest hot spots.

Photo Credit: Anwar Hussein/

Setting up Pippa

Garrett Hedlund

While not as famous as some other big star bachelors on this list, we're willing to bet this corn fed cutie is on the cusp of serious fame. He has already acted with some big names (Brad Pitt in Troy for one) and held his own opposite Gwyneth Paltrow in Country Strong, so we're not too worried about him being tongue-tied in the presence of the newly-minted "It girl" Pippa. His swoon-worthy good looks and the fact that he seems like the consummate gentleman make him a choice pick for Pippa's next boy toy.

Photo Credit: adMedia/

Setting up Pippa

James Franco

He may be ultra-artsy -- film school, art projects, short stories AND acting have this busy A-list bachelor on the go at all times, but we think he might just let a few things slide if Pippa showed up on his doorstep. They might seem like a pretty unconventional couple, but Franco is an unconventional guy, and never one to sidestep a challenge. We're not sure how the younger Middleton would react if Franco came calling, but we do think it would be a fascinating romance to watch. We're guessing he'd take her to art openings, poetry readings and obscure films that no one (except Franco) has ever heard of.

Photo Credit: HRC/

Setting up Pippa

Leonardo DiCaprio

The epitome of superstardom, Dicaprio is one of the biggest movie stars there is and perfect love match material for the sister of a princess. He may be used to models and actresses, but we're pretty sure Pippa could hold her own with this mega-star. Recently split from long time love Bar Refaeli, DiCaprio has been getting tight with Gossip Girl Blake Lively (hugging on a yacht in Cannes, holding hands). But either way, we think Pippa would make a great catch for one of Hollywood's most notorious playboys.

Photo Credit:

Setting up Pippa

Justin Timberlake

He sings, he dances, he acts – would that be enough for a jet-setting, spotlight-loving lady? We think these two would look great together and photograph really well. No matter where or when he's in front a camera, Justin Timberlake looks pulled together and always fashionable, much like the paparazzi-worthy Pippa. Plus Timberlake is pretty connected where the Hollywood elite are concerned so he could definitely woo her with access to all the best, most exclusive parties and premieres.

Photo Credit: Adriana M. Barraza/WENN.


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Who do you think would be a perfect match for Pippa? Let us know!

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