Will You?

updated 07/31/2000 AT 01:00 AM EDT

originally published 07/31/2000 AT 01:00 AM EDT

With those lapping waves, that cool breeze and the honey-colored sunsets, it seems the beach is the ideal breeding ground for the lovebug. And this summer the nippy critters have been biting all the way from Malibu—where MTV shock-comic Tom Green popped the question to Drew Barrymore on July 8—to Cabo San Lucas, Mexico. There, on July 15, Brooke Shields accepted a cushion-cut diamond ring from television writer Chris Henchy during a getaway weekend that was a surprise for the star from start to finish. "He put a lot of time and effort into planning this in the perfect way. I think even going to the airport was a surprise," says Henchy's friend, comedian Carol Leifer. And the pivotal moment? "He didn't tell me what she said," says Leifer, "other than 'Yes!' "

By Shields's description, Henchy, 36, is every woman's dream. "He actually indulges me if I ask a question like, 'Which shoes? Which pants? Which purse?' " the actress, 35, told PEOPLE in ' February. "I'll say, 'How do these make my ass look?' He's so honest, he'll say, 'I think the other ones.' "

Whatever the reason, the pair, who met while working on an NBC Christmas special in 1998, have been inseparable since Shields's two-year marriage to tennis star Andre Agassi collapsed in April 1999. While Agassi, 29, found a new match with Steffi Graf, 31, Shields-following the suicide of her friend and Suddenly Susan costar David Strickland and the cancellation of the sitcom-found consolation with the lighthearted Henchy, who, says his agent Rob Kim, "makes her laugh a lot."

Though they started out as pals, it wasn't long before Shields was hanging out on the set of Battery Park, the short-lived 1999 NBC sitcom that Henchy co-created, and stepping out to movie premieres with her new beau.

Says friend Randal Kleiser, who directed her in The Blue Lagoon: "This was the perfect timing and the perfect guy." So friends weren't surprised when they heard that Henchy, now a supervising producer on Spin City, had secretly commissioned Manhattan jeweler Stephen Russell to design a ring.

Which is more than Tom Green's pals can say. In fact, some mistook news of the gross-out star's engagement to the winsome Barrymore as just another prank. "I never know when things are real with him or not," says Bob Maurer, a producer on The Tom Green Show. "Then I saw everything in the papers, and I was like, 'Well, I guess it's true.' "

Staff at Barrymore's production company Flower Films found out firsthand when their 25-year-old boss flashed the Tiffany ring Green had bought her around the office. "They are such free spirits," another Tom Green producer, Wendy Prior, says of the pair, who met last November after Barrymore, a fan of the show, called to invite Green to appear in her film Charlie's Angels. "They're perfect for each other."

On the Angels set, where Green, 29, filmed his cameo as a boat captain early this year, "you could just tell she was attracted to him," says a crew member. "Everybody could." But it was during Green's battle with testicular cancer in March that their relationship really took off. While Green was in the hospital for surgery, says Maurer, "his face lit up when she walked in the room."

No stranger to betrothal, Barrymore has been previously engaged (in 1992, to actor James Walters) and briefly married (in 1994, to bar owner Jeremy Thomas). But in Green, who aired his own operation and once conned his grandmother into licking a sex toy on TV, Barrymore may have found her match. "She has such a great sense of humor," says her former addiction counselor Betty Wyman. "It doesn't surprise me that she has fallen in love with a comic." No doubt the gags have just begun. Says Green's pal, writer Tracy Grandstaff: "I can only imagine where they'll go for their honeymoon."

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