Going From Blonde to GrayWomen in my family do not age gracefully. We scream at mirrors, hurl expletives at our birth certificates, and yank our skin back at the mere suggestion of sagginess. My mother sobbed on her 21st birthday, for heaven’s sake — and this apple doesn’t fall far from the family tree. So when I took this challenge to find out how the older half lives by wearing a gray wig for two days, first in Boston, then in New York, I’m nonplussed. "You mean I’ll put on my usual clothes, eat my usual food, shop in the usual places — the only difference being the color of my hair?" "Think of it as a sneak preview of your life 20 or 30 years from now," they say. I haven’t been planning to let myself go gray, ever. But I’m willing to try it for 48 hours.Boston, day one of my experiment. I’ve spent 20 minutes trying to talk myself into leaving my friend Amy’s apartment wearing this wig. Said wig is actually quite fetching, much more so than my own baby-fine mop. Sure, it draws attention to certain lines around my mouth I wasn’t aware I had, but I’m shocked to report that I actually like the way I look. It’s just that, well, this thing makes me feel like I have a cat on my head. Surely the minute I walk out the door, people will shout, "Impostor!"Okay. I’ve been outside exactly 14 seconds, and no one seems to be paying attention to the young fogy inching her way down Beacon Street. Just ahead, two shirtless construction workers hammer away on an old house. The closer I get, the less they hammer — they’ve noticed me. Could they be less subtle with their let’s-go-to-the-nearest-cheap-motel stares? Then again, I don’t speak Spanish. How do I know these guys aren’t saying, "Hey hombre, don’t you just love how women can be both beautiful and intellectually stimulating at any age?" What normally seems like harassment suddenly feels more like an affirmation. If it’s possible, I think I just enjoyed being ogled.The Invisible Gray-Haired WomanEveryone at the Boston Sports Club is huffing and puffing, frantically trying to retard the aging process. Yet here I am flaunting my gray hair, sending the message that — oh, the sacrilege! — I’m okay with looking older. Suddenly, I feel giddily rebellious, like I’m taking Communion in a see-through dress. I hit the treadmill and run a few miles, slowly, so as not to disturb my hairpiece. People are checking each other out right and left, but no one even looks at me. I guess it’s true that women become invisible after a certain age. But, contrary to what I expected, being ignored doesn’t bother me. For the first time in months, I’m actually paying attention to my workout instead of worrying that my fellow gym-goers are fixating on my back fat.For no apparent reason, my treadmill suddenly shuts down. I ask the cute blond 30-something guy to my right for help restarting it. He just shrugs and keeps running. Would you treat your mother this way, young man? Or, for that matter, your prematurely-gray-yet-undeniably-hip friend?In the weight room, trainers mill about, looking bored, so I’m surprised no one asks if I need help when I struggle with the 10-pound dumbbells. I’m usually accosted by gym staff trying to improve my form. When I finally ask a female trainer for tips, she tells me to pull in my butt, without a hint of condescension: the exact opposite of the way trainers treat me without the wig. Here’s at least one positive; service types actually respect their elders.I soar to the locker room, high on endorphins and feeling buff — until a 60-ish woman with the body of Jennifer Aniston walks by. Arrgh. I’m going to have to move into the gym if I’m ever going to look that good. When I work out in New York the following day, I get a lot more attention, most notably from a trainer who rushes over to help me lift weights, chirping, "Does your back hurt? You have the posture of a slouching 13-year-old!" I choose to take this as a compliment — it’s been a long time since anyone said I look like a teenager. Not everyone is so happy to see me. A Pretty Young Thing gives me the evil eye as she waits for my elliptical trainer. What the hell is her problem? Oh, wait. 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. Had I not had gray hair myself, I probably would have written Frank off as a lech. As it turns out, he’s the most interesting and exciting man I’ve met in a while.A Little RespectFlirting may be easier in the wig, but shopping is definitely harder. At the Boston outpost of Lilly Pulitzer, where pink-and-green is forever and women of all ages buy classic shift dresses, the young blonde salesgirl smiles and says she recognizes my sundress. (I bought it at the New York store.) But she doesn’t bother to point out the sale rack or ask if I’m looking for anything special, as she does with the college-age customer who arrives shortly after I do. When I emerge from the dressing room in a caftan that’s way too big, she says it’s the only size left and turns her attention back to the coed. I make one last effort. "Do you have anything appropriate for a bridal shower?" I ask. "Really, anything in the store," she says, after trading annoyed glances with her coworker. Of course, maybe I’m getting the cold shoulder not because of my "age," but because I look like a wig-wearing weirdo.Leaving the store, I pass a bunch of kids sucking down cigarettes. A girl with a lip ring shouts, "You’re rocking the gray hair!" and she really does sound impressed. Her friend, a white kid in a Rasta hat, chimes in, "Cool granny." That’s right, you little punk.In New York, I make the mistake of trying to shop at Scoop, the current It Girl emporium, where it takes a full 15 minutes for a salesperson — a man with fake gray streaks in his hair — to acknowledge me. I realize I would feel out of place here even without the wig, if only because I have actual flesh on my bones. So I hop the subway uptown.As I sway along, I begin to notice all the older women on the train, the same way you notice pregnant women when you’re pregnant yourself. Having gray hair, I realize, has helped me find an assertive part of myself that rarely makes an appearance. Most of the older women I know make their own rules, regardless of whether they look their age. When I put on the wig, I inadvertently mimic their aggressive-but-polite behavior. I approach men. I badger salespeople until they pay attention to me. I even send my food back when a restaurant botches my order. You might say I grow up.On to Chanel. In the unlikely event that I am nominated for an Academy Award, I want Karl Lagerfeld to design my Oscar dress. Still, I’ve never felt comfortable shopping at the store. I’ve always felt too young and unsophisticated to try on those outrageously expensive clothes. But in my wig, I look, well, richer, like I belong in an $8,000 suit. Apparently the pretty, 40-ish saleswoman thinks so too. "Can I start you a dressing room?" she purrs. I rattle off my "I need something to wear to a bridal shower" spiel, and she guides me to a nubby pink-and-gray suit. "It came in this morning. It’s the only one we have in such a small size," she whispers conspiratorially. "Wear the jacket with jeans if you’re trying to look hip, or add pearls if you’re going for a more mature vibe." I hold the suit up to my body, visions of society fund-raisers dancing in my head — the same head that appears to be shedding all over the jacket! The saleswoman delicately picks the long gray hairs off my shoulders.Mortified, I scurry to the dressing room and try on the suit. And all of a sudden, I am a hologram. From one angle, I see me. From another, I see me with slightly wider hips and slightly thinner skin, the evidence of many summers spent in the sun: I see my mother. So this is it — this is what I will look like at my child’s college graduation or my 20th wedding anniversary. This is me with my life passing before my eyes in a dressing-room mirror. And it’s passing incredibly quickly: It seems like just last week I was trying on my mother’s clothes because I wanted to look her age. Now I see it’s possible to look her age — to be her age — and not begin to fill her shoes. I have my life, full of possibility, but I wonder if I’ll ever be successful enough to afford a Chanel suit, or have a child’s graduation to attend or a wedding anniversary to celebrate. My mother has had all those things, and they’ve made her feel accomplished and loved and safe. And despite her meltdown on her 21st birthday, she’s still gorgeous, fun, spontaneous, and cool. I have a lot to live up to.