Britney Spears showed off her toned and tanned bikini body on a trip to the Caribbean yesterday. She's making the most of her weeks off before touring Europe, and her dad and boys were there to join in on the fun. She was also looking friendly with her agent and rumored boyfriend Jason Trawick, who she's shared a beach vacation with before. It's hard to tell for sure what's going on with Brit's love life these days, but we're all for anything that keeps her and her family looking so happy and refreshed.

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Jada Pinkett Smith brought Will along to the Turner networks' Upfronts in NY earlier today. She was the life of the party in her short cocktail dress, running around and chatting with other actors like Kyra Sedgwick and Tyler Perry. Jada's starring alongside Michael Vartan in a new medical show called Hawthorne, which premieres next month. Meanwhile, Will has news of his own to celebrate — his production company just acquired the rights to a true story about an ex-Marine dealing with the aftermath of Hurricane Katrina.

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Ryan Phillippe and Abbie Cornish were back in LA on Monday after spending a few days at the Cannes Film Festival. They were spotted hitting the party scene together, but apparently Ryan also had some fun without his girlfriend. He was seen getting friendly with a few other blondes while clubbing with Ne-Yo into the wee hours. Sounds mostly harmless, but Abbie is probably happy to get back to their regular LA routine.

NPG

Kate Winslet chatted on her cellphone in NYC yesterday, while on Monday she took a stroll with some homemade artwork in her hands. After a whirlwind Winter, Kate's taking a break to spend time with her kids while Sam Mendes promotes Away We Go. The Oscar and dual Golden Globe winner is pretty close to earning herself another accolade — she's in the final four of the PopSugar 100! At the moment, she's slightly behind Reese Witherspoon but it's anyone's game so don't forget to vote for the winner and a chance to win Chanel!

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Lindsay Lohan sported a jumpsuit to run errands with her assistant yesterday in LA, but by evening she'd changed into a tank top and jeans for a trip to Samantha's house. Like other recent visits, this one turned into a sleepover following Lindsay's arrival at an already late hour. Whatever is going on with LL and Sam, it's clear their breakup hasn't been a permanent one.

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Ashlee Simpson has been all around NYC the past two days while Pete plays Mr. Mom with baby Bronx. She's in town to attend Upfronts for Melrose Place, which was officially picked up by CW for the Fall. Meanwhile, Papa Joe denied those pregnancy rumors via Twitter but Ashlee and Pete's one-year anniversary was plenty of reason to celebrate last weekend.

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