Awful First Dates

by Sarah Wexler

  Hysterical, True, and

  Heartbreakingly Bad

  SARAH Z. WEXLER

  sourcebooks

  casablanca

  Copyright © 2012 by Sarah Z. Wexler

  Cover and internal design © 2012 by Sourcebooks, Inc.

  Cover design by Bryn Ashburn Cover illustration by Mary Lynn Blasutta Internal art by Lena Green

  Sourcebooks and the colophon are registered trademarks of Sourcebooks, Inc.

  All rights reserved. No part of this book may be reproduced in any form or by any electronic or mechanical means including information storage and retrieval systems—except in the case of brief quotations embodied in critical articles or reviews—without permission in writing from its publisher, Sourcebooks, Inc.

  All brand names and product names used in this book are trademarks, registered trademarks, or trade names of their respective holders. Sourcebooks, Inc., is not associated with any product or vendor in this book.

  Published by Sourcebooks Casablanca, an imprint of Sourcebooks, Inc.

  P.O. Box 4410, Naperville, Illinois 60567-4410 (630) 961-3900 Fax: (630) 961-2168 www.sourcebooks.com

  Library of Congress Cataloging-in-Publication Data

  Wexler, Sarah Z. (Sarah Zoe)

  Awful first dates : hysterical, true, and heartbreakingly bad / Sarah Z. Wexler. p. cm.

  Includes bibliographical references and index.

  (pbk. : alk. paper) 1. Dating (Social customs)--Anecdotes. I. Title.

  HQ801.W652 2012

  306.73--dc23

  2011035362

  Printed and bound in the United States of America.

  VP 10 9 8 7 6 5 4 3 2 1

  Here's to great couples, who give me hope, and to great singles, who also give me hope.

  CONTENTS

  Introduction

  Chapter 1: Mr. Monopoly Money

  Chapter 2: Mr. "It's Five O'Clock Somewhere"

  Chapter 3: Mr. Sexual Super-Freak

  Chapter 4: Mr. Not-Quite-Single

  Chapter 5: Mr. Fascist

  Chapter 6: Mr. Fast Forward

  Chapter 7: Mr. TMI

  Chapter 8: Mr. Maladjusted

  Chapter 9: Mr. Critical

  Chapter 10: Mr. Out-To-Dinner Disaster

  Chapter 11: Miss "It's Not You, It's Me. No, Really."

  Conclusion

  Acknowledgments

  About the Author

  Awful First Dates: Hollywood Dispatch

  "I was a smart dating girl. I always had enough money for a cab from wherever I was. I didn't have any problem breaking a date. Like I'd say, 'You know what, this date is really not working out. Don't worry—i f you don't pick up the tab, I will, and I'll take a cab back to my house.' If you say it like you mean it, the dates can't be bad— they just end."

  —Wendy Williams

  Awful First Dates: Hollywood Dispatch

  "Most of my dates have been pretty messed-up."

  —Taylor Momsen

  INTRODUCTiON

  Recently I was interviewing Cindy Crawford for a magazine article, and as much as I wanted to focus on hearing about the ingredients in her new skin- care line, I couldn't stop thinking about the bad date I'd had the night before. A really bad date, especially one you'd had high hopes for, can rock your self-esteem and leave you feeling hopeless, not only about dating, but also about love—and on a dramatic day, about humanity in general. So at the end of our chat, I asked her if she had ever been out with a toad. She thought for a moment and then told me she's "never been on a really bad date." Right. Of course she hasn't. When I asked Jennifer Lopez the same question, she told me, "I was never a dater. I had a boyfriend from the time I was sixteen until I was twenty-three, and then I got married. I never did the date scene—I was lucky."

  Cindy Crawford, Jennifer Lopez: this book is not for you.

  It's for the rest of us. For those of us who think we are perfectly normal (or at least normal-ish), yet somehow keep meeting guys who are drunk, weird, rude, pushy, or critical, who lack basic human communication skills, who are not actually single, or who try to hump our legs before we even order appetizers. Our theme song is a mash- up of Three 6 Mafia's "It's Hard out Here for a Pimp" and Beyonce's "Single Ladies (Put a Ring on It)," something adding up to "It's Hard out Here for All the Single Ladies." And is it ever. Even if you're happily paired off now, you probably went on a bad date, or have friends telling you their weekly Saturday-night horror stories, so this book is for you too. It's for all of us who've gone on bad set-ups, bad Internet dates, dates where you wish your whole life was filmed so you could turn to the camera in a private aside, mid-date, like Ferris Bueller or Zack Morris or Michael Scott, and mouth, "Really?" This book is for all of us who have gone into a date hoping to find Mr. Right and instead met Mr. Cheapskate, Mr. Drunk-Before-Noon, or Mr. Told-Me-I'm-Fat.

  The thing is, I can't entirely hold Cindy Crawford's comment against her, because I used to be in that camp. Not that I mean I was a superhot international supermodel who had boys gawking at me in Pepsi commercials or anything, but just that I didn't always have trouble with men; I wasn't always going on bad dates. In fact, until my midtwenties, I'd always been someone's girlfriend. I'm not sure I'd even been on a date—I just met someone and he became my boyfriend, the way that so many young people do. Dates with complete strangers were for people on The Bachelor or in romantic comedies. Instead, I've basically been paired up since the third grade (seeing Beethoven with Michael Duarte, the kid with the blonde bowl cut and the really cool purple Umbros—swoon!). I was in one relationship for three years in high school, another for four years in college (it ended when I studied abroad and found an international boyfriend), and the one after that lasted for three years. I never let one guy go until I'd lined up the next sucker—er, suitor.

  Which is why it shocked everyone when I decided to break up with a boyfriend without a backup guy waiting in the wings. Nope, I was ready to try something fun and casual—going on dates! It seemed so cosmopolitan. I couldn't wait to get a manicure, glide on some red lipstick, and meet a stranger in a candle-lit restaurant for a glass of wine. After all, there had to be millions of single men in my new home, New York City. But first I had to meet them. In college, people met prospective dates in class, in intramural sports, or the next morning when they woke up in the same bed after a keg party. But postacademia, it gets tougher to date people you know, unless you make a move on a coworker, your mailman, or the guy who delivers your Chinese food. And not having a network of vouched-for men means a lot of random set-ups and Internet dating sites. Which means strangers, basically. And as I quickly learned, it also means lowering your expectations. Instead of those romantic candle-lit dinners, I got a guy whose idea of a picnic spread, after a five-mile hike, was pulling out a half-full baggie of trail mix.

  I spent the next three years going on first dates—and a couple seconds, and even a few fourths. By the end, I had my routine down: blow-dry my hair, lacquer on the eye makeup, pop in a mint, and be on my way. Ever since

  I approached the wrong guy at a coffee shop, thinking he was my Internet date, I always got to the meeting place early so it would be up to him to recognize me. If anyone would have to be embarrassed before the date even started, it would be him. While I'd wait, I'd sit and text my male friend the info I had about my date, like his username or where he told me he worked (my friend requested this, I think, because he watched too much Law & Order: SVU).

  But once the guy would show up and we'd get to talking, my funny, sprawling stories—about a horrible coworker, my psycho former roommate, snorkeling in Barbados—became reduced to pat one-liners I recited to man after man. I went on so many dates, answering the same questions so many times, that I would sometimes
pause, midsentence, not remembering if I'd just made the joke about my boss to this guy five minutes ago or if that was the guy I saw on Tuesday. It was exhausting, disheartening, and occasionally a good time, but nothing stuck. Either I didn't like him, or he didn't like me, or we mutually disliked each other. I just couldn't seem to find the win-win opposite of that. I wasn't asking for love at first sight—just like after first date.

  So I kept trying. Somehow I got the idea that it was about controlling outside variables, and so for the next seven first dates I went on, I chose the same restaurant. Still nothing. Then I widened my scope. I went out with a special-ed teacher, a veterinarian, an investment banker, a divorce still hung up on his ex, a coworker, one of my former college professors, a cop, a musician, a lawyer, an architect, a Peace Corps volunteer, and a few fellow magazine writers and editors. I suffered countless awkward good-byes on street corners, including one where the guy looked at the spray bottle on my keychain, which my dad bought me as a housewarming gift when I first moved to New York, and asked if I would Mace him if he tried to kiss me. (He did. I should have.) I tried to keep a straight face when the haughty Shakespearean actor confessed his day job for the past decade: donning the furry head of the city's back-flipping baseball mascot.

  I realize it wasn't all the guys' fault. I mean, I'm not exactly Cindy Crawford or J.Lo (but my mom tells me I'm close!). I'm sure I scared off more than a few potential suitors by talking about how I dressed my dog up as a lobster for Halloween and then tried to get him to stand in a sauce pot for a photo op (he's a St. Bernard). Or the time I tried to go wineglass-for-wineglass with a high-tolerance Brit and ended up gracelessly stumbling off my barstool on the way to the bathroom. I'm sure a few guys went to the bar and recounted to their friends the awful first date they'd had the night before—with me.

  Still, there were lots of men who proved on date one that they were far from Mr. Right. One told me my career aspirations were naive and that I'd be unemployed within the year. Another used a wheelchair but didn't seem concerned that I lived on a fourth-floor walk-up. One guy appeared promising until he announced midway through our chicken tikka masala that he'd just gotten a grain of rice stuck between his throat and his nasal passage, and then proceeded to emit a series of dreadful snorting sounds, I assume to dislodge it. It stuck around. Probably longer than I did.

  These stories became my friends' favorite conversations. At dinner parties and weddings, I was often put on the spot with, "Tell them the one about the divorced guy who compared you to his ex-wife all night and then the restaurant to the hall where he got married!" My friends loved sharing their own dating disasters, and I heard stories that were embarrassing, awkward, and usually hysterical. We spent hours rehashing and analyzing not-great dates—what his weirdness meant, and whether he deserved a second chance or we should block him on Match.com.

  I realized that single people want to hear every horrible first-date story because it's reassuring that it isn't just happening to one of us—i t's part of the process for all single folk. Coupled-up people like hearing about bad dates too, probably because it makes them elated that they aren't still single. So whatever your romantic status, you probably like hearing about other people's mishaps. As it turns out, awful first dates may be awkward, shocking, or downright painful. But in the end, they're good material.

  It seemed there was a whole community of women who wanted a place to bitch about dates gone wrong. So I made a website, www.awfulfirstdates.com, and posted a few of my stories. Then my friends started posting their stories, and within a few weeks, more than a thousand anecdotes poured in from all across the United States, England, Canada, and Australia. I decided to keep them anonymous so more people would be willing to share what they'd been through, and also not to incriminate the bad daters. The best—er, worst—of those stories, plus dozens of new ones, became the basis of this book. I've edited them, added a title for each, and then organized them into thematic categories based on the way things went wrong (the guy drank too much on the date, was weird about money, was actually married, etc.). Though there were a few stories that were tough to categorize or fit into multiple categories because the guy combined a slew of sleazy mistakes, it's shocking that there are basically only eleven different ways to screw up a first date.

  In my career as a magazine writer, I often get the opportunity to chat with hot famous people. And unlike Cindy Crawford and Jennifer Lopez, I found that most of them have had the bad luck to go on a not-so-stellar first date. Hearing from some of the world's most successful and attractive actresses, musicians, and fashion designers that even they've experienced dating disasters is kind of inspiring, especially considering that many of them are now in happy relationships. Laughing with Gossip Girl's Leighton Meester about a date she went on with a rich boy who was so spoiled he once got angry at his maid and reacted by throwing his laptop in his pool gives me hope; she is beautiful, talented, and successful, and yet still has to contend with the kind of guys who make you swear you wouldn't mind joining a nunnery. Or Salma Hayek, a talented multilingual producer, actress, and all-around gorgeous woman, who told me about a first date she went on...with the man who ended up becoming her husband and father to her child. That's the thing about bad dates: they happen to almost all of us. And though Hayek is part of the rare few for whom a bad date turns into a good relationship, even a painfully awful date can eventually make us laugh.

  Awful First Dates: Hollywood Dispatch

  "I went out with an actor who said he'd come to see me in the play I was in and then we'd go out afterward for a drink or dinner. Then he called to downgrade it to nothing after, just him coming to my performance. He showed up at intermission."

  —Kim Cattrall

  Chapter 1

  MR. MONOPOLY MONEY

  In the movie Kissing Jessica Stein, Jessica is a single New Yorker who's set up on a first date with a nerdy accountant-type who can barely make conversation. When the check comes, he gets out a calculator and starts tabulating both shares of the bill: "We split the salad," he says, "but as I recall, you ate a little bit more, including more of the arugula, which is one of the more expensive greens. I didn't have any of the goat cheese; I'm allergic. You have exact change?"

  It used to be so simple: the guy paid. Dinner, movie, whatever—on a first date, both parties knew that the check would automatically go to the man. (Of course, this system probably sucked for men, especially broke ones.) Then, along with female empowerment came female date confusion—who should pay? Even if you've had a great dinner, it inevitably makes for an awkward dance when the check comes. Should he pay, because that's the longstanding tradition? Should you offer to pay to show that you're an equal who values her independence and isn't just looking for a free meal? Should whoever asked for the date pay? Should you offer to split it, or does that show you don't like him? Will he feel like you owe him something if he pays?

  It's also difficult to decide what's worse: a flashy guy who tries to overcompensate by throwing money around on a date, or a guy who can't afford to spot you a Starbucks. More often, women have to deal with broke-as-a-joke men, or at least ones who don't want to spend their money treating a date. Those may be the worst kind, where the guy clearly has money—he just isn't convinced you're worth spending it on, a fact he doesn't hide all that well.

  It's not that the guy's financial situation is precisely the problem, or that you should start requiring a credit check before you agree to meet for drinks. I've certainly dated more than a few starving-artist types and had a great time. But the thing is, if they're not going to spend even ten bucks on your date, that's fine, but it means they need to

  be creative about planning an outing to a park or hitting a museum on free-admission day—some way to show you that if they weren't willing or able to spend money on the date, they spent time thinking about it and planning it. Instead, what many guys seem to do is to set up a traditional date, and then bust out a coupon or gift card, or do worse—like strai
ght-up asking the woman to pay up.

  Sure, Mr. Monopoly Money may eventually want to fall in love—but for tonight, he's just meeting up with you in hopes of a free dinner.

  CALL HIM MONEYBAGS

  After he asked me out, it took him over two months to finally arrange something, but fair enough: we're both busy people. He picked a fancy restaurant, and I thought over dinner we bonded well. When the bill came, I politely offered to pay half, which he accepted. But then he pulled out a 50 percent off coupon he'd printed out and told me, "This covers my half."

  BIG SPENDER

  He asked me out to dinner, then picked a fancy-schmancy restaurant. He ordered hors d'oeuvres, steak, champagne; I was impressed a grad student could afford such extravagances. When the bill came, he visibly jumped at the total. I'd only ever seen this reaction as a joke, but he was dead serious. Speechless, he slid the bill over to me to share his shock. Since it was hard to ignore the color draining from his face, I offered to split it. He thought about it for a while and concluded: "Well, um, well...no. No. You're...worth it? Yeah. You're worth it." It didn't sound like he was too convinced.

  RECESSION BONUS

  I was happy to see there was a really good-looking student sitting near me in one of my graduate classes, so I asked him out. He wanted to go to a bar, and I told him I don't drink…which he took as a sign that I needed to spend the rest of the night hearing the highlight reel of his various drunken escapades. One involved him paying for sex, and he boasted, "The price of prostitutes has been dropping because of the bad economy."