Jake and the ladies

They've been coming to Chicago the first weekend in December for 10 years—to shop, to catch up, to gossip, to have fun. They're sisters and old friends, all Women of a Certain Age scattered between Iowa and Tennessee most of the year, and two of them have known my family for decades.

So when I moved to Chicago four years ago, I became an honorary member of their group, the recipient of countless dinners and drinks and small gifts in exchange for my slowly expanding skills as a native tour guide.

And during last year's visit, these religious, patrician Southern women decided it would be fun to come a day early this year and explore everything Boystown had to offer. It seemed like a fun idea at the time, though I didn't think anything would come of the plan. Fortunately, I was wrong.

They always stay at a fussy little boutique hotel near the Hancock Center, and when I met them yesterday morning in the lobby, I was greeted with rousing cheers and maternal hugs (including one from my mom, who joined us this year) and an urgent request that we get hoppin' so we wouldn't miss anything fun.

We started with a train ride—a first for many of them, which meant pictures. Lots of pictures. Even pictures taken by our fellow passengers. (So now there are at least 10 people in Chicago who think I'm a tourist. ACK!)


Then we had lunch at Nookie's, my favorite upscale people-watching diner in Boystown. Friday at noon is not prime people-watching time, but the food was excellent and the ladies were duly impressed.

Then we started our shopping loop. We headed up Halsted to Beatnix, a vintage clothing store with tons of funky attitude and cheap little doodads to buy—and even a huge room of fabulous drag. Unfortunately, I'd forgotten about the card rack just inside the door. The one with cards that say things like Suck my dick in big letters. Oops. Paragons of gentility all, the ladies laughed politely—and only one discreetly turned a few shades whiter. And one of them even bought a leather whip.

Next up: The Gay Mart, purveyor of all things dustable, kitchy and sometimes naughty. We spent great amounts of time browsing the penis cards, and some of the ladies bought foo-foo candle holders and superhero keychains. Then we paraded over to Broadway to explore Equnox, the granddaddy of all foo-foo Boystown stores, where we lost a good two hours (and a ton of cash) enjoying even more greeting cards, candles, ornaments and other assorted crap merchandise. Just down the block: Unabridged Books, where all we did was coo over the selection of adorable books for children. Our final stop: DSW, the Valhalla of shoe stores where, curiously, only one of us found a pair of shoes to buy.

Exhausted, we headed back to the hotel to regroup and wait to be joined by assorted children and stepchildren who happened to be in Chicago for various reasons. Then Mambo Grill, a trendy restaurant short on seating and big on noise—but able to fill our tummies with delicious South American cuisine.

The ladies decided to cap off their night at the nearby Redhead Piano Bar, but Mom and I were exhausted. I'd fulfilled my self-imposed duty to expose our red-state visitors to the human faces and experiences and communities of gay people, and we went home to bed.

Today: Mom and I share the day together. Tonight: We have a second dinner with the ladies. Tomorrow: Hell week starts for the chorus show.