Slumming It

Any good investigative story about a socialite requires getting said socialite out of her element. And so we're going on a dive-bar tour, beginning at Don's Club Tavern.

Ever fashion-conscious, Holly asks what she should wear. "Not an evening gown, I hope," she says.

No, I tell her, jeans will do. Even in jeans, Holly will stand out.

And as she and her husband, Rich, walk down Sixth Avenue toward Don's, she appears to be runway ready. Holly's hair and makeup have been done, and she's wearing a strapless pink minidress over her tight jeans, along with a black leather jacket and a stunning diamond bracelet. Rich is about as dressed up as he gets, in a sport coat, jeans and a navy Polo shirt.

Matthew Morris and Kevin Hodgson, Holly's stylist and personal trainer, respectively, also meet us, creating quite the motley crew. The female bartender is annoyed and impatient with the groups' drink-ordering efforts, and she keeps eyeing Holly. There are some double takes, but most of the working-class patrons ignore us and go about their pool-playing as though no one out of the ordinary is here. Tonight's reception is not nearly as cold as the last time she visited, Holly says, when she had come in after a charity event and got glares and comments like "Go back to reality."

Rich and the guys quickly retreat to the back of the bar to play shuffleboard, leaving Holly and me like sitting ducks. Within seconds, two twenty-somethings move in for the kill. One sits next to me; the other sits across the booth next to Holly. They ask us where we're from. I'm about to pretend I don't speak English when Holly answers that she's originally from Illinois. She isn't even rude to creepy men in bars! She does, however, politely inform them that she's married, at which point they back off. (Note to guys: Look at a woman's left hand before you hit on her; Holly's 4.5-carat rock is especially hard to miss.)

Before they leave, though, they offer a round of shots. So I tell them Tuaca would be great, thank you. Holly has no idea what Tuaca is, but she's game. When the guys return with extra-large shots, her eyes widen. "They're the size of Long Island Iced Teas!" she exclaims. She's afraid to down the whole butterscotch-flavored liqueur herself, so we split the drink.

Once the aftertaste wears off and the buzz begins, we join the guys at shuffleboard. Holly's not half bad -- but she's even better at pinball. Towering over the machine in her stilettos, her long hair draping over her shoulder, Holly dominates, racking up almost a million points. We're having so much fun that we forget all about the Satire, or the Carioca, or the 15th Street Tavern -- or about going to see Boy George at Serengeti, where we originally intended to end the night. Suddenly it's 11 p.m., and everyone has to get up early the next morning. It's the most relaxed I've ever seen Holly.