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Awful First Dates: Hysterical, True, and Heartbreakingly Bad

Awful First Dates: Hysterical, True, and Heartbreakingly Bad

by Sarah Wexler

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"He spills out a pile of pennies all over the table, telling me he fished through the couch for change to pay for his big night out."

From the guy who chews on rocks to the one who has his mom tag along, Awful First Dates is filled with hilarious, cringe-worthy, holy-crap-did-that-really-happen?! stories from celebrities like Lauren Conrad and Michael Kors,


"He spills out a pile of pennies all over the table, telling me he fished through the couch for change to pay for his big night out."

From the guy who chews on rocks to the one who has his mom tag along, Awful First Dates is filled with hilarious, cringe-worthy, holy-crap-did-that-really-happen?! stories from celebrities like Lauren Conrad and Michael Kors, you'll laugh, you'll cringe-and most importantly-you'll feel better about some of the date's you've been on!

•He ate an entire bowl of dip with his fingers.

•He said, "I think we should hang out in the woods and just groove on each other."

•About thirty minutes in, he paused, took a sip of win, and then said, "So, can we go have sex now?"

Sarah Z. Wexler, a freelance writer, lives and goes on first dates in New York City.

Editorial Reviews

From the Publisher
"...the best anecdotes have been collected and put into this hilarious little book! We were seriously laughing out loud at some of the crazy things guys did - who would think it's acceptable to bring their mom to a first date?! ...but the coolest part of the book are the celebrity anecdotes between each section. It's nice to know that even gorgeous celebs like Lauren Conrad have the usual problems in their love life!" - Seventeen.com

"Wexler's collection of vignettes from real women is also sprinkled with worst-date-ever anecdotes from celebs like Jessie J, Salma Hayek, and Kelly Rowland. You'll laugh, you'll cry, you'll cringe, because the stories are authentic, hilarious, and sometimes painfully close to home...But, true romantics, fear not. Awful First Dates is not a treatise on why all the single ladies should just throw in the towel, and it manages to strike a surprisingly hopeful note in the end. Because even in the face of such eye-watering miseries, there's always a chance that the next date will be better." - Huffington Post UK

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Read an Excerpt


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 Beyoncé’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 divorcé 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—it’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 Date: 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

Meet the Author

Currently a staff writer for Allure, Sarah Z. Wexler has also written for Marie Claire, Wired, Esquire, and the Washington
Post Magazine, just to name a few. She has interviewed countless celebrities, and has had her fair share of awful dates–including one involving a pretentious Shakespearian actor resigned to life as a baseball mascot.

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