Dating Amy Read online

  Copyright

  This is a work of nonfiction, but all the names (and in some cases, occupations) have been changed in order to protect the anonymity of the characters.

  Copyright © 2006 by Amy DeZellar

  All rights reserved.

  5 Spot

  Hachette Book Group

  237 Park Avenue

  New York, NY 10017

  Visit our website at www.HachetteBookGroup.com

  www.twitter.com/grandcentralpub

  5 Spot is an imprint of Warner Books, Inc.

  The 5 Spot name and logo are trademarks of Warner Books, Inc.

  First eBook Edition: October 2009

  ISBN: 978-0-446-54380-4

  Contents

  Copyright

  Acknowledgments

  Introduction

  DATE 1: The Blind Date

  DATE 2: The Accidental Interview

  DATE 3: There’s a Penis Loose in the Cornfield

  DATE 4: The Kind of Man I Should Want

  DATE 5: The Kind of Man I Do Want

  DATE 6: Mismatched Costumes on Halloween

  DATE 7: The First-Date Breakup

  DATE 8: Picked Up a Guy Walking Down the Street

  DATE 9: Getting Some Trim

  DATE 10: But He Was So Good on Paper. . .

  DATE 11: The Money Shot of Espresso

  DATE 12: Little Twat

  DATE 13: The Mouse King

  DATE 14: The $6 Bottle of Wine

  DATE 15: My Two Biggest Assets as a Writer

  DATE 16: Fire Walk with Me Where There Are No Porta Pottis

  DATE 17: Can Men and Women Just Be Friends? Probabably Not If They’re Straight.

  DATE 18: Tiptoe Through the Tulips

  DATE 19: Unrefrigerated Sandwich: The Return

  DATE 20: Coffee Date of Sorrow, Coffee Date of Pain

  DATE 21: Didja Hear the One About the Unfunny Comedian?

  DATE 22: When Immigration Smiles at Me, I Go to Rio

  DATE 23: Lunch. Mouse. Good.

  DATE 24: Lunch. Mouse. Bad.

  DATE 25: Didja Hear the One About the Movie Star and the Midget?

  DATE 26: You Yell “Date!” and We’ve Got a Panic on Our Hands

  DATE 27: The $40 Bottle of Wine

  DATE 28: The Sophomore Date Slump

  DATE 29: The Handoff

  DATE 30: I Love Lucia

  DATE 31: A Boy Named Harry Potter

  DATE 32: The VD Outbreak

  DATE 33: Looking for Elvis

  DATE 34: Harry Potter and the One My Readers Talked Me Into

  DATE 35: Hiking in Heels

  DATE 36: Harry Potter and the Pink Corridor

  DATE 38/37: Two Dates in Reverse

  DATE 39: The Big Cheap

  DATE 40: Halloween in July

  DATE 41: “I Saw Your Name Over a Urinal in Tacoma. . .”

  DATE 42: Awkward Positions, Sexual and Otherwise

  DATE 43: Pork Loins and Pointy Ears

  DATE 44: A Bad First Impressionist

  DATE 45: Harry Potter and the Fish of Rubber

  DATE 46: Harry Potter and the Enchanted Barbecue

  DATE 47: Eric Van Halen and the Regular Barbecue

  DATE 48: Harry Potter and the Fellini Extras

  DATE 49: Harry Potter and the Last Supper

  DATE 50: Finding Mr. Write

  About the Author

  5 Spot Send Off

  For the other hopeless romantics

  and eternal optimists

  Acknowledgments

  Thanks to my agents Jenny Bent and Melissa Flashman and my editor Karen Kosztolnyik.

  Thanks also to Michele Bidelspach, Holly Henderson Root, Penny, Kurt Knutsson, ABC News, the crew from TechTV, and everyone who let me write about them.

  Special thanks to Darren Jones, who patiently helped me every step of the way, and to all the readers of DatingAmy.com, especially those who sent money, and to my parents for their unbridled encouragement of my creativity regardless of cost and inconvenience (to them, not me).

  Most of all I want to thank the men of the fifty dates—the good, the bad, and the so bad they were good—without whom this book would never have happened.

  Introduction

  More and more it seems that sex involves saddles, stilettos, and schoolgirl outfits, but my only love-life fetish is writing about it.

  Even that is new for me, because while I sometimes wear as little as possible, emotionally I am anything but an exhibitionist. My motivation for writing a book about my dating Web site was that there are just some things you can’t say on the Internet. My motivation for documenting fifty dates on a Web site in the first place was strictly financial. That’s how it started out, anyway.

  I optimistically thought I could take two wildly disparate elements—personal writing and being well paid for it—and combine them. I was sure that the Internet would give me enough exposure to land me a great job. I wanted to be wading in money while not compromising my artistic vision.

  For years, reconciling the desire for art with the desire for money had haunted my career like a needy ghost I couldn’t break up with. I had been a pop-culture writer in Los Angeles, moved to Seattle the year before, and hadn’t worked since. There just wasn’t room for yet another person to write about bands and movies and restaurants in my new city unless you knew someone, and I didn’t.

  Desperation about my career was becoming like an alarm clock whose buzzer keeps getting louder the longer you sleep in. First I worried about artistic fulfillment. I’m fascinated by men since I know nothing about them, so I pitched a fun dating column called “Single Latte” to the Seattle Times and was met with complete silence. Next I worried about getting any sort of writing work, artistically fulfilling or otherwise, and applied to be a reporter for a trade magazine about fish. After I didn’t get that job I started worrying about cash, because I didn’t have any left.

  I just knew that if I could get some notoriety I would land a great job. That’s what I told myself, anyway. My career up until then had been rocky at best. It seemed that whether I worked for a start-up dot-com or an established business, things eventually ended with me weeping and holding a cardboard box in my arms as I pushed the down button on the elevator with my elbow. Although it was never my fault, I had been laid off several times in a row and it was getting demoralizing.

  I had the same dreamy desire for the perfect blend of art and commerce in a man, too.

  I wanted a barefoot poet with tousled shoulder-length hair and skin as soft as the faded cotton shirts he wore, but he had to be great at business and have piles of money so he could support our tastes for gourmet food, fine wines, and my hobby, lying around on the couch thinking up interesting thoughts. I also wanted him to cook, share my love of horror movies, and not notice other women.

  It reminded me of the Barbie doll that I bought at an antique store two Christmases ago to auction on eBay. Her abnormally perfect body would be 39-18-33 if she were real, and researchers in Helsinki have determined that she would have 15 percent body fat. Barbie has an ever-increasing designer wardrobe, houses, cars, and the undying devotion of both Ken and GI Joe. I have an apartment, the #18 bus, and no boyfriend. My only designer clothes are from thrift stores and therefore accidental. The only thing Barbie and I have in common is a thirty-nine-inch bust.

  My particular Barbie didn’t seem to have very good taste, though. She was clad in a modest robin’s egg blue two-piece swimsuit and a black velvet choker with matching onyx-and-gold earrings. It was kind of dressy jewelry for a day of beach frolicking, even in Barbie’s confetti-and-sequins world. Her eclectic taste in accessorizing was explained when I checked the dates on her back. Her body was a vintage 1966, but her head was a decade younger: its stamp said 1976. Sh
e was a Frankenbarbie. A child somewhere had had the idea that she could make a better doll by taking part of one and forcing it onto part of another. Plop. Who cares if the choker didn’t go with the swimwear?

  I understood the unknown child’s impulse because my whole life I had mentally done that with men. If I could just take Karl the Artist’s sensitivity and unique worldview and combine them with Jason the Banker’s ability to turn any idea into money, I’d have the perfect guy. I’d better throw in Rick’s sense of fidelity, though.

  While I was certain what I wanted in a man, I had basically made it to my late thirties with absolutely no idea what I wanted in a relationship. Cross-dressing musicians, circus performers, philosophy grad students—I had always dated purely for my own entertainment. I had only had a handful of boyfriends in my whole life, and had never considered marrying any of them, but instead had dated randomly and with an open-minded verve that embraced every kind of man, regardless of income, prospects, or mental state.

  Though I had never written about relationships, analyzing them was tantamount to an avocation for me. I’m as naturally curious and tactless as yet another unknown child—the little kid in “The Emperor’s New Clothes” who points out that His Highness is stark naked. I simply cannot stand by and listen to some idiot spout off bad information, unless that idiot is me. I’m constantly debunking dating myths (or bunking them, if I agree), usually in my head but sometimes aloud if the person is spewing especially unhelpful clichés like “Love only happens when you’re not looking for it.”

  “Tasha is such a nice person, she really deserves a relationship,” someone will say. “I don’t think it’s a meritocracy, most serial killers and politicians are married,” I’ll point out. I’m a realist (when it comes to other people’s love lives anyway) and you’ll never hear me use terms like soul mate except ironically.

  Then I got what seemed like a good idea at the time: Why don’t I look for a boyfriend and document it on the Internet? I’m in a strange city, and stories about a person’s descent into madness are always popular, and, if nothing else, maybe I could find a shoulder not only to cry on but to take me out to dinner. Maybe the sheer public-ness of my search would humiliate me into finding some sort of romantic direction.

  The result of all this was Dating Amy, my literal labor of love.

  My name is Amy. I’m going on fifty dates and I’m taking you with me. . . but only if you promise not to whine “Are we there yet?”

  DATE 1 The Blind Date

  TRUE CONFESSION

  I wasn’t sure about meeting this odd man from Match.com, and, truth be told, I wouldn’t have if I hadn’t already launched the Web site and therefore needed a date to write about.

  Autumn. The snap in the air, leaves the color of flames, a holiday that includes dressing up and not buying gifts for other people—it’s my absolute favorite season. Jews consider it the beginning of the new year. I’m not Jewish, but am often mistaken for such with my pale olive skin, dark hair, and what I tell myself is a dry, Woody Allen-circa-Manhattan-style wit that doesn’t go over that well in Seattle where I live. Fall has always seemed like a time of new beginnings to me, too. It was the perfect season to launch the dating Web site that I was sure would launch my career, and I was going on my very first date for it. I felt like a sophomore girl getting asked to the homecoming dance by a senior, except that I was in my late thirties and the senior was some stranger from Match.com and we probably wouldn’t have dated under normal circumstances.

  Our abnormal circumstances were that, (1) as bold as I am about some things, I don’t believe in asking men out, and (2) he asked me out through an old ad I had up on Match.com just when I needed a date.

  DatingAmy.com was not much more than a home page that said “I flip between dating men who are like George Costanza and men who are like George Clooney. . . then quickly back again. If romance is a numbers game, it only makes sense for me to pick a biggish number.” The bizarre pressure of needing a date to write about on the Internet was standing in front of me like a fat woman in a bright orange suit holding a Drive Slowly sign as I trundled past, a single person in the diamond lane.

  Driving, slowly or otherwise, was apparently something my date did not have to worry about.

  “Sorry I won’t be picking you up,” his e-mail said. “I can’t drive. I’ll explain when I meet you. It’s not that I am a loser, though.” Hmmm, that last part would be up to me, surely. “If he can’t drive it means too many DUIs or he’s on parole,” my friends assured me. “He sounds great!”

  Like most people, I’m always nervous to meet a blind date. Unlike most people, it’s not because I think he may not like me or think I’m attractive; I’m much more worried about what I’ll think of him. Part of my hesitation—I thought pretty realistic in this case—was that he had sent a picture of himself with five cats on his head and a story from his childhood about a fish flopping in a wooden boat that was somehow supposed to be analogous to meeting me. “Maybe after we meet you can tell me what I’m doing wrong with dating,” he wrote hopefully. I was starting a list already.

  We had agreed to meet at a pub and barbecue place whose rotating sign features an apparently not-too-bright pig and cow dancing arm in arm. As soon as I stepped inside, a fortyish man with a shaved head, one dangly earring, and glasses as thick as mason jar bottoms wheeled around on his stool at the bar and asked if I was Amy. He was having a pint of beer with a lemon slice floating in it and ordered a chardonnay for me.

  Although it was Monday Night Football time, the TV in front of us was tuned to a sailing event. “Have you been watching this?” I asked.

  “Well, not exactly,” he answered.

  He went on to apologize for not picking me up but explained that he can’t drive because he is vision impaired. Really vision impaired.

  Jesus, my blind date was actually blind.

  When you’re doing online dating, it’s perfectly understandable to shave a few numbers off your age or weight and add them to your height. Less forgivable, but still in the ballpark, is putting up a picture that’s a year or two old, but how could someone omit the fact that they’re missing one of the senses? There are only five of them and sight is one of the important ones. For example, I guess I don’t really care if someone I’m involved with has a sense of taste. Sure, I’d feel bad for him and touring wine country might be less fun with him, but ultimately it wouldn’t affect me personally. Someone’s not being able to see feels completely different and like something that’s at least worth mentioning.

  “Four really gorgeous blonde girls walked in just before you did,” he said. “I told the bartender I am definitely coming here again.”

  I looked around and didn’t see any girls, gorgeous, blonde, or otherwise. Normally I would take that kind of a comment so early into a blind date as a very bad sign about where things were heading, but given the circumstances I decided to let it go.

  He mentioned the cats I had seen pictured sitting on his head. They were all his, obviously. He said that sometimes he wished that he could be lord of the manor, like in a Gothic novel, and that someone else—a servant of some sort—would attend to the demanding cats and their needs. From that point on I thought of him as Indentured by Cats. Well, as that and also as that blind guy who didn’t mention he was blind.

  “Have you noticed how people put those tacky tchotchkes by the side of the road at accident sites as a tribute to their loved ones who died there?” I floundered for a topic to try to put his handicap into perspective. “I guess nothing says, ‘We cannot accept that you were cruelly swept off the planet at such a young age’ like Beanie Babies and Mylar balloons. In Germany they make crosses and things out of the twisted wreckage of the actual cars to mark the spot.”

  “Of the European countries I like Holland the best; it’s like a second home to me,” he said, thankfully not completely picking up the conversational thread I had started. He raved about how great the Dutch are. I didn’t comment but
silently recalled an incident at a train station in Amsterdam when I changed my mind about a ticket and the agent threw a golf pencil at me and screamed, “IS THIS HOW YOU DO THINGS IN YOUR OWN COUNTRY?” Never mind that the answer to that question is, of course, yes, the experience left me scarred.

  As Indentured told me about himself, I learned that he is quite accomplished and lives a rich life, each facet of which is punctuated by beautiful women:

  He is a businessman. He’s an entrepreneur, really, as he owns his own business. He and his employees enjoy a sort of stalled adolescence akin to the guys in John Cusack’s record store in High Fidelity. Their workday consists of Yoda in-jokes, computer games that may or may not include real-life reenactments, and the hiring of cute chicks whenever possible.

  He is also a dirty old man. He told me about getting suggestive e-mails from women on Match.com who would never need to post on the Internet to get dates. “I guess it seems too good to be true that a twenty-one-year-old who is working her way through medical school by lingerie modeling is interested in me and ‘up for anything,’ but I click on the link to her Web site anyway. It’s always porn or a hooker.”

  He talked about a thirty-year-old he had beers with for five hours and how he spilled a beer on her. He called the next day and she told him he was too old and too bald and that she wasn’t attracted to him, couldn’t he see that? Despite the unfortunate word choice on her part, I couldn’t help but admire the woman’s decisiveness. Unlike me, she knew what she wanted in a man and she wasn’t afraid to say so.

  I constantly second-guess myself. Should I have given this one more of a chance? Am I too concerned with feeling chemistry right away and not allowing it time to grow? Should I lower my looks standards? How about my income requirements? Is this guy going to be the best I ever do? I mean one’s dating pool has to dry up someday and there will be a point in every person’s life when they do indeed date the best person they’re ever going to get. If they don’t end up with that person, it will all be downhill from there, by definition. And so on.

  The blind man told me all about speed dating, where singles sit at tables for two and everyone talks for seven minutes, then a buzzer goes off and they switch partners until everyone has “dated” everyone else. He said that there were ringers when he did it—again, girls so beautiful they would never have to do something like speed dating. He complained to the hostess of the event that it was unfair. He had taken a cab there and the only good-looking women were her friends and not really available. He argued that it was discrimination against the handicapped. It took me a beat to realize that by “handicapped” he meant other than socially, since as the owner of a business he had built from the ground up and a social life replete with beautiful women, he was doing better than most of my guy friends and they can all see.