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I’ve been a beautiful woman for fifty days, and no one has compared me to a summer’s day. No one has said my lips are like rose blossoms or my throat is as smooth as alabaster.

Men don’t have time for that anymore. We live in the age of transparency. Say what you mean and mean what you say. As in:

“You are a very pretty lady.”

“I think you are very attractive.”

“You look hot.”

I’ve been approached by more than six hundred men, and that’s one of the big themes I’ve discovered in their method: cut to the chase.

The directness has its charms, but like everything else about being a beautiful woman, it has its dark side as well. One suitor tried to seduce me with this line: “I would like to stalk you.” Another said, “I am in a committed relationship but am looking for a girl on the side.” Are these guys honest? Sure. To the point? Yes. Creepy? As hell.

I’m getting ahead of myself. Let me back up. I stumbled into this experiment as a hot woman. This one wasn’t premeditated. As a general rule, I dislike female impersonation. I have too many bad associations of men in skirts—Benny Hill, Uncle Miltie, Idi Amin. But sometimes there are good—or at least excusable—reasons to pose as a female.

The reason in this case is my two-year-old son’s nanny, Michelle. She’s a stunning woman. Before my wife and I hired her, I thought that hot nannies existed only in vintage Penthouse Forum letters and Aaron Spelling dramas. But Michelle—though I’ve changed her name for this book—is real. She’s twenty-seven and looks like a normal-lipped Angelina Jolie. She’s sweet, funny, has a smile straight out of a cruise-line commercial, and wears adorable tank tops.

No one can believe quite how beautiful my nanny is. Among our friends, my wife’s sanity is questioned about twice a week. Michelle is so enchanting, my wife has actually given me permission to have an affair with her, Á la Curb Your Enthusiasm. Of course, she made the offer only because she knew there was no chance Michelle would ever be interested. Michelle is too sweet, too Catholic, too loyal, too young. It’s like giving me permission to become a linebacker for the Dolphins.

In any case, Michelle remains bafflingly single. So my wife and I decided to help her find a boyfriend. How about Internet dating? we suggested. Michelle balked. She’s shy. She’s not a big fan of e-mail. Her Internet’s down. And aren’t all the guys on those sites the kind that have a drawerful of ball gags?

We told her that’s an outdated stereotype. We’d help her out. Or I would, since my job is editing and writing. I’d sign her up for a dating site, create a profile, sift through her suitors, and cowrite her e-mails. I’d be her online bouncer, bodyguard, censor, and Cyrano. All she’d have to do is give me some input and allow a few guys to buy her lattes.

She agreed. And even started to like the idea. She wrote her own introductory essay. (“I want someone who will make me laugh at the littlest thing.”) We clicked her preferences (fish and dogs are the best pets) and uploaded seven smiley, PG-rated photos with nothing more risquÉ than an exposed shoulder or two.

At 8 P.M. on a Wednesday, a couple of hours after Michelle had gone home, her profile was approved and popped up online. I’d been anxious about this. What if it went unnoticed for weeks, gathering dust in an obscure corner of the Internet?

No need to worry. Her profile was viewed within the first three minutes. Then again a minute later. The page-view counter shot up to eight, fourteen, twenty. Not quite Huffington Post numbers but brisk traffic. And then the e-mails started pinging in. A good dozen before I went to bed. I know that technically these guys aren’t e-mailing me. Still, it’s an exhilarating feeling to be so desired, if only by proxy. (And mind you, I did type in the essay and clean up her grammar.)

:-D

“Hey baby, tell me you’re coming to London,” reads my first e-mail, from a British guy who works in advertising. Michelle has given me permission to reject the guys who are clearly wrong. An ocean qualifies as a deal breaker. I zap him back, “Sorry guvnor, no plans to come over there.” I liked my response. Polite and firm—but a little flirty. I’m getting into character.

The next day, I show Michelle a half-dozen men with potential. The cute scientist with the Prince Charles ears, the guy from Long Island with eight siblings. We respond: “How are you?” “How was your week?” We keep it light, noncommittal—and short. That’s an early lesson. I’ve always been the chaser, so I didn’t realize quite how radically the balance of power shifts when you’re the chasee. Michelle could have responded with a random string of letters and numbers, perhaps an umlaut and a backward slash, and these guys would be encouraged enough to ask her on a date.

After forty-five minutes of boyfriend shopping, Michelle leaves with my son for a trip to the museum. I spend an hour crafting personal rejection notes to yesterday’s discard pile.

Then I type:

By the way—just a friendly tip: The username sexygentleman might turn some women off. Maybe too on the nose.

Perhaps it isn’t my place to say so. But, I figured, it is Michelle’s. If a beautiful woman gave me advice—solid, well-intentioned advice—I’d pay attention.

Originally, I planned to send a personal ding letter to each of the unsuitable guys. But the volume is overwhelming. By day four, we’ve gotten close to fifty approaches. I’m starting to become shockingly picky. I have a growing list of instant deal breakers:

• If the guy uses the word lady or ladies in his opening e-mail

• If the guy lists his best feature as “butt” (ironically or not)

• If the guy uses more than two exclamation points in one sentence (One enthusiast wrote: “Hello there beautiful!!!!!!!!!!!!!”)

• If the guy misspells the first word of his introductory essay. (“Chemestry is important.”) I don’t want to be a spelling snob, but the first word?

• If the guy’s opening photo features a shot in which his head is tilted more than 20 degrees to the left or right

• If the guy has a photo of his Jet-Ski or snowmobile on his page

• If the guy is wearing sunglasses, any hat besides a baseball cap, or is bare-chested in his main photo

• If the guy refers to female anatomy anywhere in his initial correspondence (e.g., “I’m not a professional gynecologist, but, uh, I’d be happy to take a look”)

Never in my life have I had such power. It’s tremendous. Yes, at first I feel guilty about failing to respond to 70 percent of these guys. But it’s just not possible. And in a way, it makes me feel better about my life as a single man. Maybe when my calls to beautiful women went unreturned, it wasn’t because I was hideous or the women were evil. It was just a matter of time management.

;-)

I am rooting for one guy. He’s got a warm, unforced smile, and he’s humble, but not falsely humble. “I’m a geek, but a cool geek because I use a Mac,” he writes. Unfortunately, Michelle rejects him. He’s a drummer and music teacher. Her last boyfriend was a musician. She’s sworn off them.

Michelle and I respond to a lot of the e-mails together. But just as often, she tells me to go ahead and reply myself while she’s away. It’s an amazing ego massage, sending e-mails as a beautiful woman. It’s so easy. I type one moderately witty thing—not even moderately witty—and suddenly I’m Stephen Colbert. I told one guy that Michelle/I hang out at the Museum of Natural History, where there are “more nannies per square inch than any other place in America,” and he responded that he was laughing uncontrollably at work. He said Michelle is “funny, intelligent, caring AND gorgeous.”

It’s not always adulation, though. A few suitors take a snotty tone. One writes that he wants to know more about Michelle but adds, “I can tell from your profile that sometimes you’re a handful.”

That’s annoying.

I respond: “What gives you the idea that I’m sometimes a handful?”

He responds: “I am so right!”

Now the bastard has really pissed me off. I click on his profile. A John Turturro look-alike with a smug smile. His opening photo shows him with his arm around a pretty woman with large breasts, as if to say, “I hang around with hot, large-breasted women, so if you are a hot, large-breasted woman, you should also hang around with me.” He likes to “work hard and play harder.” He is “VERY spiritual.”

Michelle is not a handful. In her profile, she says that she’s very open and will let you know when she’s upset. That makes her a handful?

But I have a theory. I think the son of a bitch is employing an underhanded strategy. I edited an article a couple of years ago about a book called The Game, by Neil Strauss. It’s about a nebbishy guy who decides to become the world’s greatest pickup artist, and it became exceedingly popular with a certain type of single man. One major strategy Strauss talks about is to mildly insult a beautiful woman, lower her self-esteem, thus making her more vulnerable to your advances.

So I e-mail Handful Guy as Michelle: “Have you read The Game by Neil Strauss?”

He says, “What makes you ask me that?”

Yes! Busted.

I respond: “I was wondering if your first email was a neg.” A “neg” is pickup patois for the mild insult.

He shoots back: “No, it was playful teasing. And yes, I have read the book.”

Thus commences a flurry of e-mails arguing whether his line qualifies as a neg. Finally, he brings out his trump card: “Considering that I know most of the people in the book personally from before the book was released, I’m gonna have to disagree.”

Aha. I hit the sleazeball jackpot, a longtime pickup artist. I tell him I’m glad my womanly radar warned me against him.

He says, “I was hoping online dating would introduce me to different girls than the ones I pick up and seduce in bars, clubs and starbucks. So far not.”

It was the closest thing to an admission of guilt that I was going to get.

I write, “Just remember as you wade through the dating pool [his lame metaphor, by the way]: we women are not just here to be conquered as part of the game.”

I’m a magnet for scammers. Everyone wants down my pants. Michelle probably would have sniffed this guy out eventually, but I’m proud that I saved her from a date.

I was actually prepared for the scammers and the swagger. What I didn’t expect was many men’s tragic vulnerability when faced with a dazzling woman. One guy frets that his eyes look weird in his photos because he tried to blacken out the red-eye from the camera. He just wants Michelle to know they aren’t that weird in real life.

A martial-arts enthusiast admits flat out that he’s not worthy of Michelle but wants to let her know that “you are gorgeous.”

A forty-one-year-old classical musician writes, “Not being striking in the looks department, I am someone who needs a chance to show his intellect and soul. And I realize how hard that will be when the first impression is made by pictures and written words, but I most sincerely hope you will give me the benefit of the doubt.” You want to take these guys out for a milk shake. Or sign them up for Tony Robbins. Michelle and I send them encouraging notes: “You are a bit out of my age range, so I don’t think it will work out. But I think you’re a nice-looking gentleman.”

Still, it’s rejection, and a lot of men take it hard. “Never will we share a malbec overlooking the Rio at CÓrdoba in Argentina,” writes one Harley-riding architect. “Never will we stand together in Amsterdam looking at Vermeer’s Woman Pouring Milk. Never will I hold your hand. Never will I look into your eyes. Never will you look into mine.”

A bit over-the-top, but I know what he’s saying. I will never hold Michelle’s hand, either, aside from in a game of ring-around-the-rosy.

The power of a beautiful woman’s words is beginning to scare me. One guy begins his introductory essay, “When I was a child, I witnessed a clown jump to his death from a seven-story building. It was the only time a clown has made me laugh.”

So I write him back on behalf of Michelle: “You’re funny, but too dark for a sweet girl like me.” Both of which are true.

“Just tell me I’m ugly,” he said.

A few days later, he changed his profile to an essay about his love of Care Bears and snuggling. Yes, it was a joke, but there was an underlying sense of despair. He e-mailed Michelle that he really wanted to meet her. He needs a sweet girl. His revamped profile is only for her: “I made it in response to you.”

Men will do anything for you.

;)

Michelle has her first off-line date tonight, and I’m freaking out. It’s with the scientist guy who wears a lot of Patagonia jackets in his photos. I keep staring at my cell phone, jittery as a dad with a daughter going to the prom. Forty minutes after their scheduled meeting time, Michelle text-messages me from the Starbucks where they were supposed to get together. He never showed up. “That’s it for me and online dating,” she writes. “It really isn’t for me.”

She’s surprisingly sensitive. She should have Trump-like self-esteem, but she gets stood up once and she quits the game.

I’m furious at this Ph.D. bonehead. I spend an hour tracking down his real name on the Internet. (I know his alma mater and his specialty in marine biology.) I consider showing up outside his office and asking him why he’s got the emotional maturity of a third grader. Do you know what you’ve just blown, you idiot? Plus, in one of his e-mails, the guy said he didn’t like pancakes. What kind of asshole doesn’t like pancakes?

Then I just get depressed and insecure. What did we say that made him blow us off? It wasn’t her looks. So it must have been our banter. Did we not talk enough about reef decay in Honduras? Dammit. My walk on the feminine side is over. My vicarious single life is dead.

The next day, the scientist e-mails. He was actually at the Starbucks. He was waiting outside. And Michelle, it turns out, was waiting inside. Come on! This guy can’t even find a beautiful woman in a Starbucks the size of your average living room.

But Michelle and I are both relieved. She agrees to try again. I make another plea with her to give the smiley rocker a chance. I had e-mailed him that “I had a bad experience with musicians.” He had shot back that he’s “NOT” that guy. He’s been sending us long e-mails about his family, his career, and the magnificence of xylophones. He apologizes for the length, but “they just flow out of me.” I don’t mind. Most of these guys are too lazy to form a complete thought. A rambling e-mail is better than “u a hottie.”

Michelle says she’ll think about it.

:0

Today I get the most startling e-mail yet. It’s from a guy with the screen name “watchmeontelevision.” Who could it be? Goran Visnjic? Al Roker?

I open it up. “I must confess that I am currently involved with someone but quite frankly am looking for a girl on the side. . . .

“As you noticed I have no photo to share but I periodically represent my company on national TV. I’ll be on [show you’ve never heard of on a minor cable network]. My name is [his full name here].

“I suppose on your path to finding Mr. Right I could perhaps be Mr. Right Now. . . .”

Oh boy. Did he really use the “Mr. Right Now” line? And is he actually trying to leverage his two minutes on an obscure cable network show into sex with a hot mistress? And why did the subject line say “renaissance woman”? Is that a new euphemism for slut?

I know I should have left it there. But I couldn’t.

Me: “Intriguing. What’s it like to be on TV?”

He asks me to watch him and tell him what I think. So I TiVo it. Afterward, I e-mail to ask if he was flirting with the host. He responds with a cocky e-mail about how the host isn’t his type—but “you seem like you might be my type.”

I shoot back that I’m not sure it’s a good idea: “I feel a bit guilty about borrowing another woman’s man. Do you feel guilty?”

I was hoping to see a hint of remorse, something to humanize him.

He responds: “You know how they say the forbidden fruit is always the best.”

Nope. No remorse. I tell him again that I’m conflicted.

He says meet him this afternoon for a drink, and one of two things will happen: I’ll feel uncomfortable, or I’ll want to meet him later for a nightcap.

I say maybe, but let’s keep e-mailing. We chat about travel and our favorite foods. I ask him about the craziest thing he’s ever done.

“Being a business guy who’s ballsy enough to try to be on television, contemplating running for political office”—wait, did he just say he was contemplating running for political office?—“moving to ten states for my job, romantic fantasies. (oh, that one slipped out—do you have any fantasies?)”

Uh-oh. Here we go. There’s no way I can show this to Michelle. She would be mortified.

I should just drop it, but I don’t. Why?

To teach this cretin a lesson?

Because I’m drunk with power? I’m a beautiful woman. I can make these miscreants do anything I want.

Revenge? Against men who give our gender a bad name?

Whatever it is, it’s something male. I want to take him down.

I respond, “I think food and sex make a nice combo LOL. Some whipped cream. Cherries. Maybe some chocolate syrup.”

I just want to open the door, not get too graphic.

TV guy says, “I like your fantasies involving food and sex. . . . My fantasies are a bit more risque than that, so maybe I should hold off until you know me better.”

I write, “Send them to me. Nothing can shock me.”

A total setup.

He writes back, “Let’s start with the tamest version of my most common fantasy—taking you to a strip club on amateur night (although there is nothing amateur about your photos!). I’d like to see you strip for other men, and as we’re entering the club you have on a long fur coat and you’re wearing stiletto heels, but underneath the coat I know you’ve got on little else . . .”

It’s a well-crafted, highly detailed account that stretches a good two pages.

“. . . You walk out onstage wearing a lacy black bra from which your breasts are spilling out. You have on a black thong. . . . You rip off your bra and thong, and your gorgeous, naked body is out there for all to see . . .”

It continues with an increasingly graphic description of things she does to the audience. Then he concludes: “. . . if you’d like to continue the fantasy by telling me how you’d react . . .”

Okay. This has gone into unsettling territory. I have to end it. I take the offensive.

“I found your fantasy disturbing on many levels. It made me feel dirty, but not in a good way. I felt like you were exhibiting me to other men like a piece of meat. I am not a piece of meat. I am not a prostitute. . . . I know famous people get away with a lot because of their fame. But I think its best if we end our conversations here.”

I feel momentarily gleeful about punishing this guy. Though more than a bit like a manipulative bastard in my own right.

As it happens, I have been having a simultaneous e-mail exchange with another sketchy character. This is a guy who, in his opening e-mail, said he was a “BAD boy.” Capitalized. I ask him what makes him bad. He says he’ll do things that would take my breath away. I ask him for details.

He writes “after the nice dinner and the club . . . and after turning u on with my nice attitude and sexy thoughts, we will rush to my place where I’ll begin by kissing ur sexy lips . . . kissing my way down your stomach . . . and then your inner thighs . . . [detailed description here of the licking] also . . . i really want to see more photos.”

I write back: “I’m afraid there’s been a terrible misunderstanding. When I said I wanted details of how you’d take my breath away, I meant details such as the type of flowers you’d send me, the candlelit restaurant you’d take me to, et cetera.”

He responds: “it all started with a dinner and a night at the club. i just didn’t give u details about how romantic the dinner was. . . . no photo?”

This guy is wonderfully oblivious. As if he’d only thrown in a description of the tablecloth before the graphic licking it would have been okay.

But that’s it. No more of this nonsense. No more setting guys up and then smacking them down, even if they are cheaters. This is wrong. What am I? Fourteen? Or Chris Hansen from Dateline? I can’t be wasting my time on this stuff when I have to find Michelle a boyfriend.

I feel guilty enough to write a softening note to the TV guy— who had apologized for making me feel dirty. I write that I overreacted but added that I still couldn’t bring myself to cheat with him. I send it off. Then I noticed I signed the note “A.J.” Damn! I am dumb. I’m dumber than an aspiring politician who sends dirty e-mail fantasies over the Internet. A week or so later, he e-mails Michelle again. He addresses her as “A.J.” and begs her to “come out an play.” I don’t respond.

:-)

Michelle has another off-line date, and this time I make sure to tell him to meet her inside the bar. It’s the smiley, shaggy-haired rocker. She’s giving him a chance.

In a last-minute panic attack out of Three’s Company, I call Michelle to tell her she should say she went to a Super Bowl party last week. I had e-mailed the rocker to tell him how much fun the party was before I found out Michelle got sick and had skipped it in real life.

Again, I wait with my cell phone in hand for the postdate update.

“It was pretty good,” she says.

“Just pretty good?”

“It was great. He’s very sweet.”

I feel giddy enough to do an actual fist pump. I’m investing a lot in this guy. He’s my discovery. He’s my stand-in.

I had been worried that Michelle’s online personality would be too different from the way she acts in real life. She’s usually much shyer than the hybrid we’ve created. What if he suspects something fishy? But no, Michelle told me she actually made herself act less shy to conform to her online self.

“When I got there, he said, ’What do you think?’ And I made him turn around in a circle before I said, ’Not bad.’”

I’m psyched. I’m Henry friggin’ Higgins. Michelle doesn’t yet know if the chemistry is there, but the rocker is definitely worth a second date.

I hang up, and my giddiness soon wears off. It’s replaced by sadness. A weird sadness. Almost melancholy, like something out of a Goethe novel. I realize it’s because I’m vicariously experiencing the feelings of a crush, the excitement, the possibility, both on Michelle’s part and the rocker’s.

I’d forgotten that feeling. And it’s bittersweet, because I know that I can’t experience that sensation firsthand. I love being married—I love its depth and comfort—but I miss the crush. Unless you happen to be Mr. watchmeontelevision, you don’t get to feel the rush of the crush. I’m jealous of the long-haired rocker.

:-\

The next day, Michelle pulls up a chair to my computer to go over that day’s haul with me. A whole bunch of e-mails. One cheeseball has written, “I know that you probably get tons of e-mails from dudes trying to use coy pickup lines. But I don’t care about that. I wanna know if you’re beautiful on the inside.”

I’ve gotten more believable e-mails from Nigerian barristers. But he’s right about one thing: she gets lots of dudes complimenting her on her looks. Her pretty eyes, pretty smile, pretty dimples. She’s been called the entire “attractive” entry of the thesaurus: “captivating,” “luminescent,” “radiant.”

“How many of them do you think read the profile?” Michelle asks me. I laugh and turn to look at her. She keeps her eyes on the screen.

We click on a thirty-four-year-old who describes his job as international investigator for a corporation—whatever that means. Michelle looks at his photo.

“If we have kids, they’ll have huge chins,” she says.

“Why?”

“Because I have a big chin,” she says. I stare at her chin. It’s not big. It’s not even half the size of Reese Witherspoon’s. Now, I’m sure Redbook has run a thousand articles about how even Gisele has insecurities about her body. But beautiful women don’t confess it to men so much. Maybe Michelle is starting to see me as a fellow woman. Disturbing.

The chin issue notwithstanding, a couple of days later Michelle goes on a date with the international investigator. I get the cell phone call.

“How’d it go?”

“It was just okay.”

That’s Michelle’s equivalent of “disastrous.” A date with Muqtada al-Sadr would be “just okay.”

“What happened?”

“I was really self-conscious,” she says. “He stared at me the whole time. I couldn’t even look him in the eyes.”

The next night, a second date with the rocker, at a Thai restaurant. I wait for the call. It comes too early, just ninety minutes after the date.

“He’s nice, but there’s no chemistry, I think.”

I’m crushed. I thought there was a chance. I can help her write the notes, I can pick the guys, but I can’t control that damn chemistry.

Maybe she’ll find some chemistry with Ted from Long Island, the one with eight siblings. He’s scheduled for next week. And so is “Loveable Hal.”

I know she’ll find it with someone. Not just because the e-mails from interested men keep flooding in, unabated. But because of the men themselves. The only thing more surprising than the quantity and deviousness of the creeps is the emotional honesty and fragility of the noncreeps. It’s a side of men that other men just don’t get to see.

It’s enough to bring out the nurturer in anybody. Which is why I log on to the dating service and do a search for “depressed” and another one for “lonely.” I find this:

The next day, Michelle and I write him a note: “I just wanted to say that I think it’s great that you take care of your mom. There aren’t enough nice guys in this world. I don’t think we’re right for each other (I don’t believe in long-distance relationships), but I think you’ll be a catch for some lucky girl.”

Well, it’s something. To paraphrase another guy with a double identity, with great beauty comes great responsibility.

A few weeks later, Michelle dumped me. She let me down easy— “I think maybe I need a break from Internet dating,” she said. But I knew what that meant. I was getting the boot. I was no longer her Cyrano.

I tried to convince her to give it another shot. But when we logged on and saw a note from screen name “Violentbunny,” that was it. She was finished for good. (Violentbunny: you, sexy-gentleman, and Topnotchlover need to have a good brainstorming session.)

Michelle said she’d just wait and hope that love came to her. Which I thought was a terrible idea. But it actually did. Six months later, she started dating an old friend she knew from when she worked at a Washington, D.C., hotel. They’re still together.

I wish I’d been the one to find her love. But Michelle told me that I helped. I got her back into the dating mind-set, back to thinking about relationships. Without her great Internet Dating Adventure, she says, she’d still be single and lonely. I hope she’s telling the truth.

Regardless, my dating career is over for now. I’ve got mixed feelings. Being a beautiful woman had its perks. The nonstop positive attention comes to mind. But it was also an emotionally draining experience. The amount of rejecting I had to do was mind-boggling. Every day it was “no, no, nope, no thanks, no.” And not just to the sleazy guys. Sometimes to kind, vulnerable men. Type the wrong thing and you’ll send these fellows into a tailspin. I never before thought of the built-in guilt that comes with having a pretty face.

It was draining, too, trying to suss out the schemers. There were a huge number of people out there pretending to be what they aren’t. Including me, of course. (Incidentally, a colleague of mine goes into Internet poker rooms and pretends to be a woman, because he says his opponents assume women are worse at poker. I can’t decide whether taking advantage of sexist stereotypes is ethically acceptable.) There’s a lot of deceit, boasting, and creepiness that you’ll find in Internet dating.

But the semi-anonymity of the Internet also makes it an honesty amplifier. Men will open themselves right up, laying bare their fears, insecurities, and hopes. My months of e-dating convinced me there are plenty of mensches out there. Or maybe they’re just sleazy guys who had their sensitive sisters write notes for them.

© 2009 A. J. Jacobs