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Pippa Middleton News, Pictures, and Videos

Pippa Middleton Brings Boyfriend James Matthews to Dinner with Mom Carole

Pippa Middleton steps out of a restaurant with her mom Carole by her side after dinner on Thursday (January 14) in the Chelsea neighborhood of London, England.

The 32-year-old younger sister of the Duchess of Cambridge brought along her on-again boyfriend James Matthews for the dinner date.

Rumors are swirling that Pippa and James are already moving in together after recently rekindling their relationship.

The couple competed with each other and her brother James Middleton in a 50-mile swim-run race in Sweden just a few months ago.

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Pippa Middleton & Her Brother James Jet Out of St. Barts

Pippa Middleton keeps her shades on as she heads to board a private airplane on Thursday (January 7) in St. Barts.

The 32-year-old sister of the Duchess of Cambridge, Kate Middleton, was joined by her brother James as the pair headed home after their annual family holiday, though Kate was not in attendance.

PHOTOS: Check out the latest pics of Pippa Middleton

While in St. Barts, the sibling duo spent some quality time together playing tennis and grabbing lunch.

It looks like Pippa and James started their New Year off right!

20+ pictures inside of Pippa Middleton jetting out of St. Barts…
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Pippa & James Middleton Grab Lunch & Play a Game of Tennis

Pippa Middleton makes a quick exit from Nikki Beach with her brother James on Sunday (January 3) in St. Barts.

The 32-year-old younger sister of the Duchess of Cambridge, Kate Middleton, looked chic in a floral peach dress for her midday meal with her 28-year-old brother.

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Later that day, Pippa and James were spotted playing a couple games of tennis nearby.

It’s believed that the two are in town on their annual Caribbean family holiday. She and James were spotted arriving in town just the day before.

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Pippa Middleton Lands in St. Barts with Her Brother James

Pippa Middleton and her younger brother James walk off a private plane after arriving in St. Barts on Thursday (December 31).

The siblings are in town for their family’s annual Caribbean vacation, though their sister Kate Middleton was not in attendance.

It is not known if James‘ girlfriend Donna Air was in attendance on the vacation, but she did take to her Instagram account to wish her followers a Happy New Year.

“We made it to the end, Wishing you ALL a very happy 2016! #happynewyear #cantwait A fresh canvas to paint beautiful things ❤️,” she captioned the below pic.

A photo posted by Donna Air (@airdonna1) on

30+ pictures inside of Pippa and James Middleton arriving in St. Barts… More Here! »

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Pippa Middleton Has a Ladies Lunch Post-Split From Nico Jackson

Pippa Middleton cozies up in a black and white polka dot scarf as she leaves the Ivy Chelsea Garden restaurant on Saturday afternoon (October 23) in London, England.

The 32-year-old younger sister of the Duchess of Cambridge, Kate Middleton, was grabbing lunch with a group of gal pals who she could be seen hugging as she left.

PHOTOS: Check out the latest pics of Pippa Middleton

Earlier this month, Pippa split from her longtime love Nico Jackson after dating for three years.

It looks like Pippa is coping with the separation fairly well, having been spotted catching up with exes Alex Loudon and James Matthews as well as being seen out with a mystery man!

10+ pictures inside of Pippa Middleton after getting lunch…

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Pippa Middleton & Nico Jackson Split After 3 Years of Dating

Pippa Middleton and her longtime boyfriend Nico Jackson have called it quits after dating for the last three years, according to People.

The 32-year-old younger sister of the Duchess of Cambridge and the 37-year-old banker have not been seen spending too much time together as of recently, but they were spotted last on September 18 in London.

Pippa has been catching up with several of her ex-boyfriends over the last few months. She was seen having lunch with ex Alex Loudon just a few weeks ago and also spent a lot of time with former beau James Matthews during a St. Barts vacation and while competing in the Otillo race in Sweden together.

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Pippa Middleton Goes for a Friendly Lunch with Ex Alex Loudon

Pippa Middleton chats with her ex-boyfriend Alex Loudon while grabbing lunch together on Friday afternoon (September 25) in London, England.

The 32-year-old younger sister of the Duchess of Cambridge dated Alex, a former professional cricket player and broker, back in 2011 and they even attended the royal wedding together.

PHOTOS: Check out the latest pics of Pippa Middleton

Pippa and Alex broke up two months after attending the wedding and she has been dating banker Nico Jackson for the last three years.

FYI: Pippa is wearing Chatelles slippers.

30+ pictures inside of Pippa Middleton having lunch with her ex… More Here! »

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