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Perpetual free spirit and princess of Hollywood royalty, Drew Barrymore, 37, recently announced her betrothal to high-end art consultant Will Kopelman, 34, prince of one of New York's poshest families. If opposites attract, their wild-child vs. white-collar upbringings may just land them in A-list happily ever after.
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Drew: Born into a film dynasty-actors John and Jaid for parents, legendary screen star John Barrymore Sr. as grandpa, and Steven Spielberg (inset) playing fairy godfather-Drew hangs with aliens in E.T. at 6, hosts SNL at 7, parties all night at Studio 54 by 10 and heads to rehab (for the first time) by 13.
Will: Son of former Chanel president Arie Kopelman and socialite mother, Coco, Will studies at The Taft School in Watertown, Conn., and cheers on the Yankees while big sister Jill Kargman hangs with school pal (and another Spielberg goddaughter) Gwyneth Paltrow.
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The rebellious Drew gets engaged (for the first time) at age 16 to socialite Leland Hayward. Spielberg sends her a quilt with a note to "cover up" for her 20th birthday after she poses nude for Playboy in 1995. A few months later she flashes David Letterman on live TV.
Will graduates from East Coast bastion Boston University and spends free time indulging in elite hobbies like shooting (targets, not animals) and watching Woody Allen flicks. After switching coasts, his 1,546-square-foot West Hollywood loft is featured as "The Best Bachelor Pad in L.A." in the May 2007 issue of Elle Decor.
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Drew racks up an impressive five engagement rings and two divorces. Her former fiancés include gross-out comedian Tom Green (top left), Strokes drummer Fabrizio Moretti (2nd top left) and Beverly Hills 90210 star Jamie Waters. Her production company, Flower Films, is also prolific, launching 2000's Charlie's Angels (top right), among other films, and landing Drew on the list of highest-paid Hollywood actresses.
Will scores a part in the film Intern, penned by his sister and costarring Kathy Griffin and Joan Rivers. He also dips a toe in the Hollywood dating pool, squiring Disturbia actress Sarah Roemer (top right) and Laura Flynn Boyle (lower right). Meanwhile, he establishes himself as an art dealer with Silicon Valley billionaires and A-list clients like Robert Pattinson and Death Cab for Cutie's Ben Gibbard.
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Drew and Will are first spotted dancing at trendy Hollywood club Music Box in February 2011. But Drew tells Jay Leno they'd met a few years prior: "We actually went on a few dates, but it just wasn't the right time." The couple reconnect at a party and fall hard. Will proposes with a 4-carat diamond (Drew's sixth sparkler) in Sun Valley, Idaho, over the holidays. The couple wastes no time starting a family, adopting a shepherd-mix puppy once fostered by Twilight actress Nikki Reed. Now rumor has it their family may be growing-with a glowing Drew seen reportedly carrying a sonogram of their would-be heir apparent. Mazel!