Have Him at Hello by Rachel Greenwald - Excerpt

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H AV E H I M A T H E L L O
Confessions from 1,000 Guys About
What Makes Them Fall in Love . . .
or Never Call Back
Rachel Greenwald
T hree Ri vers Press

NEW YORK
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Copyright © 2009, 2010 by Rachel Greenwald
All rights reserved.

Published in the United States by Three Rivers Press, an imprint of the
Crown Publishing Group, a division of Random House, Inc., New York.
www.crownpublishing.com
Three Rivers Press and the Tugboat design are registered trademarks of
Random House, Inc.
Originally published in hardcover in slightly different form in the United

States as Why He Didn’t Call You Back by Crown Publishers, an imprint of
The Crown Publishing Group, a division of Random House, Inc., New York,
in 2009.
Library of Congress Cataloging-in-Publication Data

Greenwald, Rachel.
Have him at hello / Rachel Greenwald.
1. Single women—Psychology. 2. Men—Psychology. 3. Dating (Social
customs) I. Title. II. Title: Have him at hello.
HQ800.2.G74 2009
646.7'7—dc22 2008050509
ISBN 978-0-307-40654-5
Printed in the United States of America
Design by Cindy LaBreacht
10 9 8 7 6 5 4 3 2 1
First Paperback Edition
www.ThreeRiversPress.com

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Have Him at Hello

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ឭ CHAPTER 3
What He Said
Top Ten Date-Breakers

During a First Date
This chapter reveals the most common date-breakers men
described that occurred during a first date and what you
should do about them.
As you read the reasons why men didn’t call women
back, keep in mind that the goal here is not to scare you
away from dating, give you a litany of regrets about the
past, or place any blame. At all. The goal is to figure out
what illusionary triggers are keeping the men you’d like to
see again from getting to know the real you.
One of the key insights I gleaned from my one thou-
sand interviews is that if a man doesn’t call a woman back,
it’s because by the end of the first date he perceives her as
fitting an unflattering female stereotype. A woman says or
does a few small things (the date-breakers) that lead to
this stereotype. Even though we all know what the word
| 27 |
28 | Rachel Greenwald
“stereotype” means, pause for a moment to really absorb this defi-

nition: a stereotype is an oversimplified, exaggerated image of a group
(such as “Football players are stupid” or “French people are un-
friendly to tourists”). People use stereotypes to quickly catalog the
world around them in the absence of in-depth knowledge. In the
dating world, men use stereotypes to efficiently evaluate women
given the limited information they can glean during their first date.
You know what I’m talking about because women equally stereo-
type men on first dates. You wonder: is he the Mama’s Boy? The
Player? The Workaholic? What’s crucial here is for you to recognize
the most common stereotypes men attach to you based on seemingly
trivial date-breakers—so that you can avoid them next time.
And what’s important to remember is that because of the rea-
sons described in chapter 1 in the New Dating World section (e.g.,
a better match being only a mouse-click away), men are trying to
rule out—not in. So they are overly focused on determining if you
fit a negative female stereotype, rather than a positive one. I’ve cho-
sen the most vivid examples from my Exit Interviews to illustrate
each stereotype, but use these examples to extrapolate what you
might be doing, even if in less pronounced ways. If you don’t recog-
nize yourself in the preliminary description of each section, I en-
courage you to keep reading to the end, because familiar behavior
may become apparent. The “Sound Familiar?” questions at the end
are designed as a final checkpoint for accurate self-assessment.
While I’ve numbered the reasons men gave according to fre-
quency, the importance of each reason is not inherently reflected by
its ranking but rather by whether or not it describes you. If a reason
at the bottom of this list seems more relevant to your dating style,
that’s actually the most important item you should focus on.
The notes section at the back of this book provides the raw fig-
ures of the 4,152 reasons given by the one thousand men about why
they lost interest in a woman.
Have Him at Hello | 29
#1 DATE-BREAKER
The Boss Lady

It felt more like a business dinner than a date.
—Carl, age 28, Philadelphia, PA
I get enough aggression at work all day. When I

come home, I want to be with someone softer, more
nurturing. —Jacob, age 31, New York, NY
Her attitude was like, “This is how it’s going to be”

instead of “This is what I’m thinking but I’d like to hear
your thoughts too.” —Kiran, 52, Seattle, WA
The top date-breaker men reported came down to one thing: dom-
inant behavior. Many men basically said the date failed because
they’d rather hire her than date her. They may respect her intelli-
gence and admire her capabilities, but that doesn’t necessarily mean
they’re attracted to her. They weren’t saying they wanted someone
simple, needy, or uncomplicated, but they didn’t want to feel tense,
belittled, or neglected in their personal relationships.
The term “boss” here reflects men’s attitudes that certain
women seem argumentative, competitive, controlling, not feminine,
too independent, not nurturing, or some combination of the above. In
other words, some women give off a “masculine” vibe. Of course,
women don’t use the same terminology to describe this behavior. In-
stead, women might rightfully identify themselves as persuasive, ca-
pable, street-smart, organized, modern, confident, or forthright. You say
“potato”; he says “potahto.”
This is a tough spot for contemporary women, particularly
those who have successful careers. It has roots in behavioral science:
in the end, men and women are all a lot like Pavlov’s dog. We be-
have according to the ways we’re rewarded. If Pavlov’s dog learned
that he got a doggie treat every time he barked, then he’d eventually
start barking a lot. In the workplace, women (like men) are rewarded
with promotions, bonuses, praise, and respect for taking charge and
being capable. As women have risen up the corporate ladder, they

have adopted many traditionally male characteristics to succeed,
whether they work in finance, law, retail sales, or party planning.
It’s not easy to just switch off this alpha personality after you leave
the office. But that comes at a cost.
One man told me that most women he meets today would pre-
fer he “admire their accomplishments rather than their butts.” Wel-
come to Dating 101. If you’d take professional respect over lust, you
might have just lost that second date. I call these Boss Ladies part of
“The Cinderella Generation”: they broke the glass ceiling but broke
their glass slipper along with it. Of course it’s unfair. Luckily I don’t
believe your only choice is between a big promotion and a date with
a guy you’re crazy about. Landing both can be as simple as gaining
awareness of the issues and making a few easy adjustments.
While it’s hard to transition from taking charge, focusing on the
bottom line, and organizing schedules, it’s imperative to grasp that
men say the “image” of the woman they want at 8:00 PM isn’t the
same image of the woman they want at 8:00 AM. He’s not buying
red roses for his fabulous female colleague with whom he works
side by side during the day—the one with whom he debates a client
strategy and who he thinks would do a damn good job running the
company. He says he’s not intimidated by her (though perhaps he
is). He really does respect her. Many men just don’t picture coming
home to her (or, more precisely, the stereotype of her) after a long
day. In fact, as far as professions go, 44 percent of the men I polled
in a separate online survey responded that their first-choice profes-
sion for a woman they’d like to marry is “schoolteacher.”1 And this
poll was conducted in 2008, not 1950!
Throughout my interviews, most men clearly told me they
wanted an intelligent, accomplished woman with whom they could
share stimulating conversation. It wasn’t really her job title that
tipped the scale as they debated calling her back, but whether or not
1
See notes section about Craigslist survey.
she seemed to have a soft

The issue is not what you are
demeanor—as far as they
or aren’t at your core, but
could tell during a one- or rather that trivial comments
two-hour first date. This or actions are screening you
time frame is crucial be- out before he can really get to
cause ultimately the issue is know and appreciate you.
not what you are or aren’t at
your core, but rather that
trivial comments or actions are screening you out before he can re-
ally get to know and appreciate you.
Are You The Boss Lady?

The Boss Lady encompassed six categories of behavior, as shown
below. Although some of these overlap, each comes with subtle dis-
tinctions. Do any of these descriptions ring true for you . . . even a
little piece of them?
ARGUMENTATIVE
Paul, a twenty-eight-year-old art dealer from Miami, FL, told me,

“I think women feel they have to prove they’re smarter than me if
they want to be taken seriously.” Several men expressed frustration
that they couldn’t find a woman who challenged them intellectually
but didn’t bulldoze them at the same time. The sentiments I heard
repeatedly were that men do want to hear what their date thinks, yet
they want the discussion to be a fun, intellectual exchange of
ideas—not a heated argument.
Scott, a forty-one-year-old doctor from St. Louis, MO, griped
about being on one date when he felt “like the whole evening she
was practicing for the final exam of a debate class. It was point-
counterpoint all night.” He described one example about reading
the menu at a restaurant to select an appetizer to share. He men-
tioned that he didn’t like curry. His date shot back, “Who doesn’t
like curry? How can you not like curry?”
Scott said the issue about him not liking curry was argued for a
couple minutes, and no matter what he said, she had a “challenging

retort.” She quoted facts about everything from nutrition content to
parents who don’t push their children to try new foods. It’s not that
she delivered her comments in a mean voice, he explained, it’s just
that the whole thing got exasperating. “Jeez,” he sighed to me, “all
she had to do was say, ‘Okay, you don’t like curry, then do you want
to share the artichoke dip?’ You know, [it] wasn’t that big a deal,
but I had gone out with another woman that week who was more
easygoing, so when the curry thing started things off on the wrong
foot, I began to tune out.”
I bet Scott’s date thought she was being playful or that she was
simply “sparring” with him to prove she was up to the challenge she
thinks men want. But surprisingly trivial or mundane verbal ex-
changes like these can build up in the male mind as symptoms of a
larger issue. Scott told me about two other small examples from
that date similar to the curry issue and ultimately admitted he had
labeled her “an argumentative person.”
Bart, a twenty-eight-year-old political speechwriter from Wash-
ington, DC, described his recent date with Holly, one of my clients.
He said she was everything he was looking for . . . until their date
vibe plummeted. He explained how they had been joking around
about their parents when he mentioned that his mom was a house-
wife. According to him, Holly’s smile faded as she said, “Careful
now . . . you’re treading on a touchy subject. I hope this doesn’t
mean you expect your wife to stay home with the kids. Personally, I
love my job and expect to keep working after I start a family.” Bart
said the discussion turned serious as they espoused their views
about women, work, and family. He told her he’s open to whatever
his future wife wants to do. She asserted that he might say that
now, but later he’d probably fall back on the traditional housewife
model he saw growing up. They debated this thorny issue, and Bart
concluded Holly was “sort of combative.” He said he’s not attracted
to that type of girl. When I gave Holly this feedback, her response
was a curt “Well, he just has a fragile ego.” Yet she had earlier told
me she hoped to see him again. My observation is that it was too
early to know whether he had a fragile ego or not. If they’d gotten

to know each other better on subsequent dates, they would have
been able to more accurately evaluate each other’s views and then
make an informed decision about any future potential.
COMPETITIVE
Some of the dating stories I heard about The Boss Lady had a com-
petitive vibe. The women in this category were slightly different from
the argumentative ones (who seemed to argue for the sake of proving
their knowledge or intelligence), because these women wanted to
“win.” Whether they were trying to win an unspoken contest of
name-dropping about who knew more important people in Manhat-
tan, or who knew more about wine, or who got fewer hours of sleep
after a late-night party, it didn’t matter. This type was a “one-upper.”
Men told me that when a woman tried to “trump” their comments or
stories, it sparked a competitive instinct rather than a romantic feel-
ing. Guys didn’t think “How impressive!” Nor did they say “Oh, how
cute, she crushed me at bowling!” Sure, I heard a few expected stories
about dates where the man didn’t like losing on the tennis court, golf
course, or even with an Xbox. But that’s an old lesson most of us
know: let him win a little to soothe his ego.
On a basic level, competitive women were described as being
focused on winning the point, rather than being accommodating
and gracious (which was considered more ideal for a long-term
partner). This type of competitiveness emerged in subtle ways. Sek-
ouWrites (his real name, which he gave me permission to use, and
yes, it’s all one word) is a thirty-six-year-old writer from New York,
NY, who told me a story about a woman he perceived as competitive
when they were simply trying to figure out where to rendezvous. He
met Alma at his book signing party in Brooklyn and was very at-
tracted to her. When SekouWrites called her to confirm the time
and place for their first date, Alma told him she had a meeting that
day starting at 5:00 PM that would last two hours and asked if he
could please come to her office lobby at 7:00 PM. He said, “Oh,
sometimes meetings run late, so why don’t you just call me when
it’s over and I’ll come pick you up? I’m only ten minutes away.” She
replied, “What’s wrong with my plan? I think it’s better if you just
come at seven PM. I’ll be ready.”
He told me it wasn’t that he didn’t like her plan—he was just
trying to strategize about the best possible way to organize the eve-
ning. But they sparred back and forth for several minutes discussing
the logistics of where and when to meet. While his description cer-
tainly contained shades of the “argumentative” woman, SekouWrites
emphasized that it felt like “all she cared about was whether her plan
‘won.’ ” He said she tried to act “jokey” but her voice sounded to him
like a kid chanting on the school playground, “My plan’s better than
your plan!” Ultimately they met at 7:00 PM in her lobby, but the rest
of the evening he was overly sensitive to certain comments. When she
said, “Let’s walk instead of taking a taxi,” he heard, “I know what’s
best!” He admitted he was probably too judgmental, but regardless,
he didn’t want a second date.
I repeatedly saw throughout my interviews that once a guy had a
whiff of something he didn’t like, he started to look for other evi-
dence to back up his initial hypothesis. Sure enough, he always found
stuff. I suppose when someone looks hard enough, he can find just
about anything.
Jake, a twenty-six-year-old mechanical engineer from Sacra-
mento, CA, had another story that illustrated a similar competitive
streak. He recounted an evening with a woman named Carla whom
he never called back. They were introduced through a mutual friend
hosting a dinner party who had hinted separately to Jake and Carla
in advance that they might like each other. Jake considered this
dinner party their first date, and he was eager to meet Carla since his
friend had described her as beautiful, petite, and sassy. When they
met in person that night, they chatted casually before sitting down at
the group table. “This woman has potential,” he thought. Because the
party was small, most of the conversation tended to include the whole
group. At one point the topic turned to global warming, and things
got dicey as one guy stated he didn’t believe there was even much of
a crisis. “Didn’t you see the Al Gore film?” asked Carla. “Of course,”
replied the other guy, “and it was ridiculous.” “Well,” said Carla, “I
saw the film three times and one of the scientists whom Gore
quoted was a professor of mine at Yale. I can tell you his data is
rock-solid, backed by Nobel Prize–winning scientists.” “It’s all polit-
ical propaganda!” claimed the other guy across the table.
The barbs flew between them for several minutes. Watching
Carla spar at the table that night with her “adversary,” Jake felt like
she cared less about sharing her point of view and more about who
knew more facts and “winning the round.” He admitted that he
thought the other guy was making inflammatory remarks, but it was
Carla he was watching closely. He said he wants a woman who can
share her ideas but still knows how to handle herself gracefully when
confronted by a jerk. He said her style made him “cringe in his chair”
and he told me, “She was competitive . . . aggressive . . . always try-
ing to one-up the other guy. I can see how that approach goes a long
way if she’s your divorce attorney, but who wants that in a girlfriend?”
CONTROLLING
The Boss Lady who’s successful in her job usually likes to be in con-
trol. She is used to taking the reins. But when this quality overflows
into a date with a new man, it can be a turnoff—at least in the be-
ginning. Later, when two people get to know each other better,
they tend to adapt to a rhythm where one person makes more of the
decisions, or at least certain types of decisions, so that day-to-day
choices as a couple don’t turn into power struggles. But because most
guys are used to their own way of doing things (whether they are
twenty-two or seventy-two), they bristle at women whom they per-
ceive as too controlling on a first date.
I want to reiterate something important here: it doesn’t matter
on the first date whether deep down you really are or aren’t a “con-
trolling” person—or whether you have any other negative traits, for
that matter (we all do). And no, I’m not suggesting you trick him
into thinking you’re someone you’re not. But if he perceives you as
controlling on a first date, my research indicates that he’s not going

to ask you for a second date. Case closed. But that doesn’t mean a
relationship with the “real you” wouldn’t make him (and you) happy,
even if you are indeed “controlling.”
When a man gets to know you better later on, there’s a good
chance that the very style he might have labeled “controlling” on date
number one will be viewed as “organized” or “forthright” when bal-
anced by all the other wonderful qualities he comes to appreciate in
you. With the advantage of time, he looks at you through different
glasses. As you date and get to know each other, you will learn
whether your styles mesh or not. Perhaps your controlling nature will
be a problem in your dynamic as a couple, perhaps not. The object
early on is to prevent his knee-jerk reaction to a negative stereotype
from ruining a potentially fabulous relationship that could develop.
The cues reported to me that signaled a woman as controlling
often revolved around surprisingly mundane events during a date,
such as opening an umbrella or even loading the dishwasher. Ryan,
age twenty-six, a hedge fund manager from Newark, NJ, told me
that it was raining the night he met Tina for their first date. They
met at her apartment and planned to walk to a nearby café for a
drink. He had forgotten to bring an umbrella, but luckily Tina had
an extra one. During the elevator ride down, Tina offered a litany of
comments: “Here’s an umbrella . . . No, don’t open it now . . . Just
put it in your jacket pocket . . .” Ryan laughed when he recalled the
story. “I didn’t even know her for five minutes, and already she was
telling me what to do and when to do it!” He said that he takes in-
structions all day long from his boss, so he isn’t looking for that on
weekends. When I sounded surprised that a few words in an eleva-
tor determined the outcome of the evening, he said, “Look, by itself
it wasn’t a big deal, but it made me aware of the issue, and after a
couple other similar things she said during the rest of the date . . .
well, I meet a lot of great girls, so I just moved on.”
Another man I interviewed, John, a thirty-seven-year-old ad-
vertising executive from Berkeley, CA, told me a story about
Shauna. He had liked her initially—she seemed warm and bright,
and they shared a unique passion for playing marathon sessions of

Scrabble. The momentum was growing between them, and at the
end of their first date, she volunteered to cook him dinner next time
at her apartment. The second date at her place started off well, ex-
cept he noticed she was very particular about certain things. Minor
stuff didn’t really bother him right away, but it started to build up.
He remembered that she asked him to take his shoes off at the door,
reminded him to put her CD back in the right sleeve when he turned
on the music, and suggested (twice) he let the red wine breathe be-
fore he poured it. After dinner they played Scrabble and then kissed
passionately on her couch until 1:00 AM. Finally she said it was get-
ting late. He still planned to ask her out again at that point and of-
fered to help her load her dishwasher before he left. She grinned
and said, “Thanks, I’d love that.”
But within two minutes the mood changed. Shauna told him
he had incorrectly loaded a heavy iron pot on the top rack next to
the wineglasses and that they might break. She jumped in and
placed it “correctly” herself. He felt that “only a control freak would
care about how a dishwasher was loaded . . . [instead] she should
have cared more that I was helping in the first place.” Although he
smiled in the kitchen at her and muttered, “Oh, sure, sorry,” her
dishwasher comment reinforced a “controlling” stereotype that had
started to form in his mind earlier. He said to me, “I don’t need that
for the next fifty years.”
When Shauna and her friends later dissected why she never heard
from John again, I’m sure the dishwasher never came up in their
post-date analysis!
NOT FEMININE
Heterosexual men are, by definition, attracted to women, not men.

That may sound obvious, but today the line is often blurred between
what’s masculine and what’s feminine. Some men told me that
women made little comments or gestures that reminded them of being
at work or with their buddies. Hugh, a twenty-nine-year-old lawyer
in Hanover, NH, mentioned a woman he once chatted with at a

young-alumni happy hour event. Toward the end of the evening,
she asked him for his e-mail address and suggested they stay in
touch through her LinkedIn network. He said LinkedIn is a business
network—not a social network like Facebook—and it made him feel
like their connection was more professional than flirtatious. When I
pressed him further (“Was that the only reason you weren’t attracted to
her?”), he recalled that the LinkedIn remark was consistent with some
other observations he made about her: she was wearing a business suit,
she didn’t wear any jewelry, and she had a short haircut. He said he
thought she was smart but wasn’t attracted to her masculine vibe.
Owen, a thirty-two-year-old management consultant from
Charlotte, NC, recalled asking a woman for her number and she
handed him a business card. He assumed that meant she wasn’t in-
terested in anything personal, so he later tossed the card in his desk
drawer and didn’t ask her out. Though he did say one day he might
call to use her services (she’s a Realtor). He said it seemed “more
feminine” when a woman wrote her number on a napkin or piece of
scrap paper in “girly handwriting” and even cuter when she reached
for his cell phone and typed it in. That’s when he knew the connec-
tion was personal, not professional.
Other men described “masculine” women who had a brisk power
stride when they walked across a restaurant or down the sidewalk, or
women who tried to hail a taxi instead of letting the man do it, or
women who used phrases such as “The bottom line is . . .” Business
lingo especially sounded masculine to many men and doused a flir-
tatious vibe. Carl, a twenty-eight-year-old architect from Philadel-
phia, PA, said, “We talked too much about our jobs, which were in
the same industry . . . The conversation seemed transactional. It
felt more like a business dinner than a date.”
Cameron, a fifty-one-year-old banker from Minneapolis, MN,
initially told me he didn’t know why he didn’t call Carol back for a
second date. He sighed: “The chemical attraction just wasn’t there.”
I probed, “When did you decide you weren’t attracted to her? Do
you remember your initial reaction when you saw her?” He finally
remembered that when he arrived at Starbucks for their date, Carol

was already seated and talking on her cell phone. She gave him a
half smile to acknowledge him and mouthed, “Gimme a sec.” She
quickly returned to her phone call and proceeded to give instruc-
tions, presumably to her assistant, about wiring money to a client’s
account. Her formal business tone during her call made him feel like
he was back at the office. He couldn’t shake the business vibe after
she hung up. He never quite felt a spark ignite between them. Phys-
ical attraction is so ephemeral—a few little gestures or work-themed
comments can extinguish a romantic mood.
Date wardrobe also played a role here. Perhaps not surpris-
ingly, most men are still old-fashioned in feeling a positive initial
response to feminine clothing. I’m not suggesting women wear a
hoop skirt and carry a parasol, but the reality is that we’re dealing
with quick, instinctual reactions—think cavemen! If a man shared
an anecdote about The Boss Lady during my phone interviews, I
asked if he remembered what his date wore. As you’d expect, many
had no clue, but they remembered if they were attracted to her or
not. Her clothes were likely part of that memory, whether the men
noted them consciously or not. So I followed up with my online
survey and I asked more specifically, “What would you really like to
see a woman wear on a first date, if she’s someone with long-term
potential?” A whopping 68 percent of the answers involved a skirt
or dress. Noticeably absent were corporate pantsuits (and military
uniforms!). Comments about “hot jeans” only accounted for 17 per-
cent. One man summed it up, “If you’re a girl, dress like a girl!”
Certainly what constituted feminine or sexy was individual and
varied by age group, but the themes of “looking like a girl” and avoid-
ing businesslike vibes cut across the board.
TOO INDEPENDENT
Here’s a popular mantra I hear from many single women: “This is

who I am. I’m not going to pretend to be someone I’m not. I want a
man, but I don’t need one.” My reaction is always, “Of course!” But
with that mantra comes a prickly attitude. And how do men respond
to that, whether the mantra is verbalized or only intuited? Do they
fall all over themselves trying to pursue her, romance her, and prove
they want her just the way she is? Umm, not exactly. What men told
me is that this attitude is a turnoff, and they can spot it right away.
Mateo, age forty-five, a lawyer from New York, NY, said, “I don’t
want a damsel in distress—I’m not looking to rescue anyone—but
it’d be nice to feel needed sometimes.” Another man, Jay, a twenty-
three-year-old film production assistant from Los Angeles, CA, told
me how he went to pick up a date one night and when she got into
his car, she didn’t buckle her seat belt. He suggested she strap in and
tried to make a little joke out of it by saying, “Buckle up for safety!”
She turned to him and said in a breezy tone, “I can decide whether to
buckle my own seat belt or not.” He quipped to me, “Yeah, so that
just made me want to lean over and smother her in kisses, right?”
Garrett, a thirty-nine-year-old venture capitalist from Atlanta,
GA, was one of five men I called for a series of Exit Interviews for
one of my private clients, Claire. As standard protocol prior to start-
ing my process, I asked Claire to guess why each of the men had
not called her back. She speculated that Garrett in particular was
turned off by her Bible study references, since he told her he wasn’t
very religious. But instead Garrett told me “the calamari story.” He
took Claire to his favorite seafood restaurant and suggested they
order calamari to start. Claire frowned. So Garrett said, “Oh, you
don’t like calamari?” She replied, “I do, actually, I just prefer to
make my own choices.” A week later when I gave Claire her cumu-
lative feedback from all five interviews, I reported that four of her
ex-dates essentially said she came across as too independent and
having hard edges. I recounted some examples, including the cala-
mari story (with Garrett’s permission). She claimed that what Gar-
rett told me wasn’t even true. She remembered that exchange but
said she told him, “I like calamari, but the shrimp sounds good
too.” Who knows what was actually said. It doesn’t matter. The fact
is that Garrett built a case in his mind from an accumulation of her
“vibes” and seemingly insignificant dialogue. In his words, “She was
too independent and probably some big feminist.” He lost interest

in pursuing her.
By the way, during the in-depth hour I spent on the phone
with Garrett, he only once mentioned religion (referring to his
observation that her Bible study showed she had passion for some-
thing), as one of the things he liked about Claire.
NOT NURTURING
A common impression about The Boss Lady is that she’s not the
nurturing type. And ultimately, if a man is thinking about long-
term potential with someone, he might evaluate what kind of
mother she’d be to his kids. Most guys don’t come out and say this
explicitly, but after all my interviews, it’s clear to me from the sto-
ries they tell that this evaluation (fair or not) happens more than
you’d think. An example from Mitch, a thirty-eight-year-old med-
ical supplies salesman in Boston, MA, is typical.
Mitch was tired of dating and wanted to find a relationship
that could lead to marriage. One night he had a great date with a
woman named Audrey, and they ended up in her apartment at the
end of the evening with a bottle of wine. As they chatted, he no-
ticed a puppy roaming around, which he said Audrey ignored after
a brief introduction (“Oh, that’s my dog, Rex . . .”). As he sat there
observing her during the next hour, he couldn’t help thinking to
himself, “If this is how she treats her pet—totally ignoring the poor
puppy, his water bowl is empty, she’s not playing with him—
imagine how she’d treat her children!” He never called her again.
My guess is that Audrey loves her puppy and, if she’s anything like
most dog owners I know, dotes on him all the time. She was prob-
ably trying to give Mitch her full attention that night. This sounded
unfair to me, but that’s what made up his mind. After hearing
enough variations on Mitch’s perception during my research with
other men, the message came across loud and clear: if a guy is in a
serious dating mode, he is often monitoring little things about you
to predict what kind of mother you’ll be to his future children.
Zachary, a thirty-four-year-old doctor from Irvine, CA,

lamented the fantastic woman he dated once who conveyed she
wasn’t the nurturing type. In the context of a discussion they had
about a 2002 documentary film they had both seen, Searching for
Debra Winger, she said, “I love my career and I don’t want kids any-
time soon.” He left wondering when “anytime soon” was (two
years? ten years?) and if she would ever want kids. He admitted
maybe she didn’t want him to feel pressure to fast-track their rela-
tionship and might have been saying that for his benefit. But if that
was true, it backfired. Maybe she genuinely didn’t want kids any-
time soon, so they weren’t a match. But Zachary wanted to find a
woman whom he could eventually marry and start a family with, so
he backed off after she emphasized her career.
It’s not only whether your behavior or your words seem nur-
turing or not, but also what you do for a living that factored into
men’s first-date impressions. After my online survey revealed
“schoolteacher” as the most preferred job for someone with future-
wife potential, the next-most-popular preferences were “nurse” and
“chef.” The top three roles all reflect nurturing stereotypes. Also, a
few men specifically mentioned in my phone interviews “I’d never
date a lawyer” or “I don’t want anyone with an MBA, thanks!”
Andy, a thirty-six-year-old stockbroker from Dallas, TX, told me
about one woman he dated: “She was a career woman, but I’m
looking for a woman who just happens to have a career.”
Yeah, all that irritates me too (especially the MBA part!). But
reading between the lines, I didn’t conclude that men were inter-
ested in only dating women with certain professions. Of course a
female corporate lawyer, for example, can have a marriage that is as
wonderful as that of a schoolteacher. I don’t think these men liter-
ally meant they wanted or didn’t want specific careers, but rather
they wanted the initial stereotype of someone nurturing, caring,
giving, and patient.
SOUND FAMILIAR?
You may not have noted similarities to yourself among The Boss
Lady anecdotes thus far, as it’s not always easy to recognize yourself
through other people’s stories. So you can use the self-assessment
questions below to verify whether men might be stereotyping you as
The Boss Lady before they get to know the real you.
at work . . .
❏ Do you command attention when you walk into a room?
❏ Would you describe your job environment as follows: the harder
you push for something and the tougher you are, the more you
will succeed?
❏ In past performance reviews or casual feedback from coworkers,
have you ever heard any of these comments:
“I admire how you stand up for what you believe in!”
“I’m just glad you’re on my team; I’d hate to be on the other side!”
“We love your persistence!”
“Were you on the debate team in high school?”
with your friends and family . . .
❏ Has anyone ever told you “You’d make a great lawyer!”?
❏ Are you the one who always organizes the plans for a group outing?
❏ Do you ever use the phrase “Wanna bet?”
on a date or with a past boyfriend . . .
❏ Do you sometimes meet a guy after work before going home to
change your clothes?
❏ Has a guy ever described you as “challenging” or “tough”?
❏ Has a guy ever told you, “Jeez, don’t be so defensive! That’s not
what I meant . . .”
your personal philosophy . . .
❏ Do you believe you’re usually right?
❏ Are you proud that you don’t let anyone take advantage of you?
❏ Do you think, “I’m very independent—I’d like a boyfriend, but I
don’t need one!”
If you answered yes to more than five questions above, you may
be perceived (or misperceived) as The Boss Lady. There’s no doubt
you’re smart, successful, and admired, and of course you shouldn’t
change who you are deep down. But you may consider tweaking
some of the things you do and say on a first or second date. Men
who don’t know yet how fabulous you are may think you’re The Boss
Lady and miss the chance to get to know you better on the next few
dates.
Have Him at Hello

Throughout my research, many anecdotes initially made me won-
der whether some guys were better off knowing early on that a
woman—a nameless, faceless woman (certainly not you or me!)—
was argumentative, controlling, or competitive, in order not to
waste time in a doomed relationship with her. But suddenly I real-
ized that I’m The Boss Lady too! I hope my marriage isn’t doomed.
I’m controlling and argumentative, just to name a few of my lovely
qualities. Guilty as charged. Yet my husband seems happily mar-
ried. And I certainly haven’t hidden my personality 24/7 for seven-
teen years. So I asked him one night about it, and the conversation
went something like this:
ME: I’m kinda controlling and argumentative, huh?
HIM: (laughing) Is this a test?
ME: No, no . . . really. I’m curious.
HIM: Then, yeah, obviously you are . . . why?
ME: You’re happy being married to me though, right?
HIM: Definitely.
ME: So, what’s wrong with you? I mean, how can you be happy
if I’m not a rosy ball of sunshine? [Not my best metaphor, but
that’s what popped out of my mouth.]
HIM: Because I know you so well. [He was quiet for a few moments
and then smiled at me.] I take the good with the bad . . . I
guess overall there’s more good than bad.
No one’s perfect. That’s why I believe so strongly that the goal of

the first date should be simply to encourage a man (assuming he’s
not an ogre) to ask you out again: so he can get to know you better,
you can get to know him better, and both of you can start to see the
whole package. This package deal is probably why people are asked
in marriage vows whether they take their mate “for better or worse.”
If you have tendencies that might cause you to be perceived as
The Boss Lady, here are five suggestions to help you soften your
image and allow you to choose whether a second date happens or not.
1) CHANGE THE DELIVERY
Some of the negative perceptions that a man has about The Boss
Lady are reactions to how she speaks and acts, not necessarily to her
inherent personality. This is key because there’s something you can
do about it (and will want to do about it one day with a guy you’re
really interested in). The distinction lies in delivering your com-
ments with a softer approach rather than combative assertions, with
witty banter rather than dry job-speak. The “good type” of Boss
Lady appears straightforward, real, and confident, while the “bad
type” seems demanding, harsh, and self-righteous. It’s not easy to
strike the right balance. He says he doesn’t want someone too inde-
pendent, but he doesn’t want someone needy or clingy either. He
doesn’t want someone argumentative, but if you agree with every-
thing he says, he’ll think you’re boring.
Take an example from the dinner party mentioned earlier when
Jake watched Carla aggressively argue about global warming. Since
men said they want a woman who sparks interesting conversation
but doesn’t draw a line in the sand, how could she have delivered
her opinions differently? Carla could have gracefully told the other
guest, “All I know, whoever’s right, is that it’s great to see an issue
like this get so much discussion . . . ,” and then bridged to a differ-
ent topic. With a comment like that, there are no winners or losers
in the debate. Carla hasn’t forsaken her identity to get a man.
Rather, this comment makes Carla look like the bigger person.
Toning down your conversation style from combative and de-

fensive to gracious and even a little flirtatious goes a long way. Try
sprinkling qualifying or humbling words into your dialogue, such as
“I think” or “maybe” or “sometimes,” which allow for disagreement
and aren’t adversarial. Rick, a forty-seven-year-old marketing man-
ager from Newport Beach, CA, put it this way: “I want my future
wife to have her own mind but still be on my side. It’s not that I
want her to agree with everything I say, but if she takes the contrary
stance all the time, it makes me feel like we’re adversaries instead of
partners.” I guess a little nuance goes a long way.
2) PLAY GAMES
A different challenge is warding off the “business dinner ambience.”

This can permeate a date with a simple question like “So, what do
you do for a living?” Sharing your current and past work history is
common getting-to-know-you conversation, but next time try
something new. Instead of dutifully providing your job title and a
résumé summary, try answering that dry question with a playful or
flirty guessing game, or even adding a funny story about something
that happened to you once at work. Obviously try to read the guy
while you’re doing this to make sure you don’t become annoying,
but you can respond something like this (in person or via e-mail):
HIM: So, what do you do for a living?
HER: Well, here’s how I spend my days. See if you can guess
what I do. My office always smells great. When clients
walk in, they usually have problems or pain. I’m not a doc-
tor, but I use sterilized tools. My clients include stressed-
out professionals and women who can’t get pregnant. By
the time they leave, they’re usually happier and hopeful.
HIM: (smiling) Hmmmm . . . Are you a really nice human re-
source lady with a bottle of Valium?
HER: Nope. Guess again.
HIM: I was thinking maybe a masseuse, but then you wouldn’t
exactly use sterilized tools, would you?
HER: Nope.
HIM: Maybe a therapist, like a shrink? But again, I can’t imagine
what the tools are.
HER: Okay, you’re getting closer. I’m a type of therapist: I’m an
acupuncturist!
HIM: Wow, that’s interesting!
HER: Yeah, and you wouldn’t believe what happened one day
when . . .
This guessing-game format sparks more intriguing banter than
the typical what-I-do-for-a-living spiel that you hear on most first
dates. But think it through in advance, as clever clues can be elusive
on the spot. And by the way, it’s not that every piece of background
data should be turned into a guessing game or riddle (how annoying
would that be?!), but simply realize how exchanging demographic
data points can feel like filling out a census form. The Boss Lady
needs to mix it up, steer clear of business vibes, and sometimes turn
factual into flirty.
3) PLAY BALL
For The Boss Lady with a competitive edge, I want to recommend

something about different types of games: bowling, golf, Scrabble,
etc. While a few men mentioned they didn’t like losing a game, I
don’t want you to conclude that it might be better to avoid games
altogether on first dates. It’s fine to play sports or board games, and
you don’t always have to let him win, but remember what your par-
ents and coaches told you when you were younger: “It’s not whether
you win or lose; it’s how you play the game.” Exhibiting nonag-
gressive, playful mannerisms is crucial during any game. So rather
than betting who wins the next round of golf, pumping your fist
in the air after a great putt, and shouting “Who’s your daddy!” you
can compliment one great stroke he takes, ask for pointers on
something that’s not your best skill, joke about the movie Cad-
dyshack, or take a break midgame to rest and observe the beauty of
the course.
Realize that if you really like the guy, you might be channeling
all your nervous energy into overfocusing on the game rather than
relaxing and having fun. Regardless of why your competitive streak
emerges, save the victory dance for later when he knows you better.
Later he’ll see that you both have different areas of excellence, that
you both can thrive on competition by challenging one another to
do better, and that your common interests are something to enjoy
as a couple. But none of that will be evident on the first date if you
tend toward The Boss Lady profile, because he might want a re-
match but not a second date.
4) LOOK LIKE A WOMAN
It’s easy to peg an all-work-and-no-play gal in a cocktail party

crowd simply from her attire. She wears the same professional outfit
from work to the after-hours event. It’s a suit jacket with a struc-
tured, tailored fit. It’s probably expensive and it’s definitely black. It
probably covers a stiff blouse. At work, conservative clothes allow
you to be taken seriously, but they’re not exactly alluring by candle-
light (except maybe in some kind of boss-secretary sex fantasy, but
save that for much later . . . ).
Whenever I start working with a new client, one of the first
things we do is review her dating clothes. My clients usually have
impressive wardrobes. They tell me, “Oh, let’s not waste time going
through my closet; if there’s one thing I know, it’s that my clothes
are fabulous!” They reassure me that their labels are Armani,
Donna Karan, whatever, and how their friends always compliment
them on what they’re wearing. But that’s my first red flag: when I
hear that the compliments are coming from female friends, I push
even harder to review their clothes. Because what impresses a woman
is not necessarily what creates physical attraction in a heterosexual
man. Women tend to be wowed by fashion, which is great, but be
sure the outfit looks feminine and flattering on you. Upon close in-
spection, most of my clients are not dressing femininely, no matter
how much status their labels have.
Of course, I’m not suggesting that “feminine clothing” trans-

lates as Laura Ashley lacy dresses. But, for example, you could wear
a skirt (not too tight, not too short) and a vibrant or soft-hued top
that shows your curves, revealing a little bit—yet not too much—
cleavage. Avoid tight jeans and low-cut blouses on a first date even
though you might think (or might be told by friends) you look
“hot.” Looking hot reflects a certain type of goal on a first date—it
signals a hookup goal, not a find-my-mate goal. Also, men repeat-
edly told me that longer hair is more appealing (longish layers,
shoulder-length or below).
5) LOOSEN THE KNOT
Like the Rolling Stones say, “You can’t always get what you
want . . . but you just might find you get what you need.” I think
this is one of the most essential truths in a happy marriage. While I
watch women parade by on dates night after night, year after year,
with their mental checklists of what they want, they rarely seem to
focus on what they need in order to make themselves happy. One
friend of mine, happily married, confided in me once that she chose
her husband “because he took the knot out of [her] stomach.” At
first I thought that sounded really unromantic, but then I realized
she has a very uptight and nervous personality, and that’s exactly
what she needed. I think a calming influence made her happier
through the years than what fell off her checklist when she met him:
height and hair.
So consider treating the cause, not just the symptom. In addi-
tion to focusing on softening your approach, think hard about the
men you’re selecting. For The Boss Lady, a nurturing type of guy
can be optimal (e.g., the male versions of teachers, nurses, chefs).
Yet that profile is the opposite of what most successful career
women are looking for. They typically want the high-powered
types who have equal or higher professional wattage. But we all
know those types: they are usually domineering, self-centered, and
workaholics. Your best match is probably a man who balances you
emotionally. Rather than seeking someone similar to you, consider

the men with more traditionally “female” energy, i.e., nurturing,
sweet, surrendering, patient. Really ask yourself this question: Could
you be happy in a marriage where you’re The Aggressive One and
he’s The Gentle One? Where you’re The Breadwinner and he’s
The Stay-at-Home Dad? Most women initially reject this marriage
model, but I encourage the hard-core Boss Lady to sit with this
portrait for a minute. The next time you’re on a date with a sweet
guy who you think is “not your type,” please consider that he might
be just what you need.
If You’re The Boss Lady . . .
WHAT’S HOT: WHAT’S NOT:

1. Feminine skirts 1. Professional pantsuits
2. Flirtatious banter 2. Shop talk
3. “Thanks for helping me!” 3. “Do it this way!”
4. “What do you think?” 4. “When I want your opinion,

I’ll tell you what it is.”
5. Jada Pinkett Smith or 5. Hillary Clinton
Kate Hudson or Rosie O’Donnell

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What are some common date-breakers that men described?

What are some common date-breakers that men described?

What is one of the key insights the author gleaned from interviewing men?

What is one of the key insights the author gleaned from interviewing men?

Gree_9780307406545_6p_00_r1.

qxp 1/27/10 11:47 AM Page iii

T hree Ri vers Press

Copyright © 2009, 2010 by Rachel Greenwald

All rights reserved.

Originally published in hardcover in slightly diﬀerent form in the United

Library of Congress Cataloging-in-Publication Data

Printed in the United States of America

Design by Cindy LaBreacht

First Paperback Edition

Top Ten Date-Breakers

“stereotype” means, pause for a moment to really absorb this deﬁ-

Have Him at Hello | 29

The Boss Lady

I get enough aggression at work all day. When I

Her attitude was like, “This is how it’s going to be”

being capable. As women have risen up the corporate ladder, they

Have Him at Hello | 31

she seemed to have a soft

Are You The Boss Lady?

Paul, a twenty-eight-year-old art dealer from Miami, FL, told me,

couple minutes, and no matter what he said, she had a “challenging

Have Him at Hello | 33

early to know whether he had a fragile ego or not. If they’d gotten

Have Him at Hello | 35

controlling on a ﬁrst date, my research indicates that he’s not going

Have Him at Hello | 37

and they shared a unique passion for playing marathon sessions of

Heterosexual men are, by deﬁnition, attracted to women, not men.

in Hanover, NH, mentioned a woman he once chatted with at a

Have Him at Hello | 39

remembered that when he arrived at Starbucks for their date, Carol

Here’s a popular mantra I hear from many single women: “This is

Have Him at Hello | 41

too independent and probably some big feminist.” He lost interest

Zachary, a thirty-four-year-old doctor from Irvine, CA,

Have Him at Hello | 43

Have Him at Hello

Have Him at Hello | 45

No one’s perfect. That’s why I believe so strongly that the goal of

1) CHANGE THE DELIVERY

Toning down your conversation style from combative and de-

A diﬀerent challenge is warding oﬀ the “business dinner ambience.”

Have Him at Hello | 47

For The Boss Lady with a competitive edge, I want to recommend

4) LOOK LIKE A WOMAN

It’s easy to peg an all-work-and-no-play gal in a cocktail party

Have Him at Hello | 49

Of course, I’m not suggesting that “feminine clothing” trans-

5) LOOSEN THE KNOT

emotionally. Rather than seeking someone similar to you, consider

If You’re The Boss Lady . . .

WHAT’S HOT: WHAT’S NOT:

2. Flirtatious banter 2. Shop talk

3. “Thanks for helping me!” 3. “Do it this way!”

4. “What do you think?” 4. “When I want your opinion,