That’s the same look I’ve given older people who use the cardio machines during the morning rush hour. I’ve often ranted that anyone old enough to be retired should use the gym at 3 p.m., when those of us who have to work don’t need it. The gagging sound you hear is me, choking on my own medicine.Gray Hair = Ma’amGoing to the gym is child’s play next to braving the bar scene. I ask my friend Amy to meet me at the Cactus Club, Boston’s most popular pickup joint. "Of course I’ll come," she says. "The only thing more entertaining than watching you, the shyest woman in the world, try to hit on men will be watching you do it in a gray wig!"Blonde me is used to being let into clubs first, so I ignore the line of people waiting to get in and head straight for the velvet rope. The bouncer, who looks like he just graduated to big-kid pants, is not amused. "Ma’am, the line is over there." I’ve been ma’amed! No woman dressed in a leather miniskirt and stilettos is a ma’am, no matter how gray her hair!Inside, the bartendress serves me immediately, probably because I stand out in the sea of brunettes and blondes trying to catch her attention. My margarita is so cold I get brain freeze after one slurp. As I will my head to thaw, I lurch into the guy standing behind me. "Whoa! Are you okay?" he asks. His name is Matt; he’s a 28-year-old ad exec. And we’re off…chatting about the election, whether or not Boston is really more uptight than New York, and whatever happened to REO Speedwagon. I keep waiting for him to ask me what a mature woman like me is doing in a place like this. He has to have an older-woman fetish, right? Not exactly. "I have a thing for short hair," he says when I playfully ask if I’m his type. Oh. So my hair color doesn’t give him pause? "It looks arty, like you dyed it gray on purpose. Besides, I’ve been concentrating on your face, which is pretty, and your skirt, which is short."I’m flattered, but still not convinced that my hair is a nonissue. So I introduce myself to Jason, a 40-ish accountant with graying sideburns. He’s flattered that I’ve approached him. I ask if he’s noticed my hair. "Okay, yeah, you’re a little gray, but you still seem like someone I’d want to talk to. Besides, I liked that you didn’t feel like you had to change your hair. It’s cool when a woman is brave enough to be herself." This guy will never know how much I spend on blonde highlights.Several more men hit on me before the evening ends, and I have to concede that gray hair hasn’t stood in my way in Boston. New Yorkers will be different, I’m convinced.But no. I’m taking off my raincoat in the lobby of the Hudson Hotel bar when I’m accosted by Drunk British Guy. "Come home with me, I love older women," he spits, his eyes half closed. And then John, a 30-year-old investment banker, swoops in and tells DBG to beat it. Even when you look old enough to have been a guy’s third-grade teacher, he still feels he has to rescue you."So what’s with the wig?" asks John after we talk for a few minutes. My, aren’t we observant — and direct. "How’d you know it was a wig?" I sputter. "You keep scratching your head." Oh. Right. "Are you really gray under there?" he asks. "What if I am?" I counter. "Just curious, because you’re cute and I want to get to know you. And honestly, you don’t look over 38." What!? I’m only 29! I nearly snarf my Pinot Grigio through my nose.Later, Frank, a dashing lawyer in his late 40s, offers me a martini and his barstool. His eyes stay locked on mine — in refreshing contrast to men my age (the guys I usually flirt with), who can’t keep their eyes off my breasts. Frank pours on the compliments. "I had to talk to you. You have this great smile. Not many women in here look as happy as you do." My cheeks turn the color of Merlot. Since I’m incredibly introverted, I usually hear, "Wow, you’re a lot friendlier than you looked." And this man was drawn to me because I appeared to be having fun! Going gray has done what multiple glasses of wine and years of coaching from my friends could not: helped me relax. Furthermore, I’ve found myself talking to men of all different stripes, not just the ones who meet my rigid requirements.