Lorraine Olivia

Look, up in the sky—it’s Lorraine Olivia, our Miss November 1990. Born in Illinois, Lorraine was based in Newark, New Jersey, though rarely on land—as a flight attendant in the late eighties, she spent most of her time 30,000 feet in the air. After brief stints with a car dealership and a pharmacy, Lorraine was hired with United Airlines, and served travelers from the Pacific to the Atlantic coasts. Her ideal passenger? “Anyone who helps to pass the time on a four-hour flight,” she jokes. “What they don’t teach you in stewardess school is how to deal with unaccompanied children who like to play with the call button!” A die-hard sports fan—her favorite pastime is baseball, and she professes an abiding love for the Cubs—Lorraine was at a post-game party in Chicago when she was approached by a Playboy photographer. “I thought I’d heard every line, but this beats them all,” said Lorraine to the photographer—but when he produced a business card, she agreed to come in for a test shoot. “I never dreamed of being a Playmate,” she says succinctly, “but opportunity knocked!” With Playboy, Lorraine did some high-flying publicity stunts, including an appearance on the “Fresh Prince After Dark” episode of The Fresh Prince of Bel-Air. (Lorraine can be seen behind Carlton in the famous conga line scene. Bunny hop!) In her free time, Lorraine is something of a sportswoman herself—she plays racquetball, tennis and golf, and never misses a chance to root for the Cubs. As for those Boys in Blue, they root for Lorraine, too—she dated 1989 N.L. Rookie of the Year Jerome Walton, and when one amorous Cubbie spotted in her in the stands, he gave her his autograph and phone number. “The cutest Cub is Mike Bielecki,” she giggles. In a man, Lorraine loves strong hands and a sense of humor, and can’t stand selfish guys, especially those who hog all the blankets in bed. If you’re not a ball player, you might get by with a good joke and a king-sized duvet.