It's Okay to Sleep with Him on the First Date: And Every Other Rule of Dating, Debunked

It's Okay to Sleep with Him on the First Date: And Every Other Rule of Dating, Debunked

by Andrea Syrtash, Jeff Wilser


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Product Details

ISBN-13: 9780373892785
Publisher: Harlequin
Publication date: 06/25/2013
Edition description: Original
Pages: 288
Product dimensions: 5.56(w) x 8.10(h) x 0.78(d)

About the Author

Jeff Wilser is a writer whose work has appeared in GQ, New York magazine, Esquire, Mental Floss, the Los Angeles Times, the Chicago Tribune, and many other publications. His television appearances have ranged from BBC News to The View. He collaborated with Marc Ecko on the book Unlabel: Selling You Without Selling Out. Wilser is also the founding editor of The Plunge, a website for grooms, and his relationship advice has been syndicated via McClatchy to a network of more than two hundred newspapers.

Read an Excerpt

The rules start before you go on a single date. They affect your psychology and overall approach to romance. Some of them are explicit: "Always let the man pursue." And some of them are well-accepted bits of conventional wisdom:

· You're intimidating to men because you're too successful

· Always let the man pursue

· You find love when you're not looking

· Don't be too picky

· Men love bitches / Nice guys finish last

· Expect love at first sight



On Sex and the City Miranda had an epiphany: Mentioning her job to eligible men in a bar was a buzz kill. They would never be interested in her, because she was a lawyer. After this depressing realization, Miranda decided to approach dating differently and took on the persona of a perky stewardess at a speed-dating event. She attracted a great guy instantly and noted, "Men are threatened by good jobs. They don't want a lawyer." She unlocked the secret: men don't want to be with a successful woman.

I can't tell you how many smart and fabulous single women in Manhattan have uttered the same reason (or excuse, depending on your perspective) for why they're not dating. They've wondered if men are "intimidated" by them. A former client of mine once said, "As long as I'm in this job, I won't attract someone. Guys don't want to be with women they think are too smart."

Kind of condescending to men, no? Besides, the opposite is true. Every decade since 1939, the University of Iowa has conducted a study in which participants are asked to rank the most important qualities they want in a future mate. In the most recent study, in 2008, male participants ranked intelligence as one of the top five attractive qualities out of eighteen that a woman can have. (In case you're wondering, housework was ranked near the bottom at #14.) Not since the 1950s have studies supported the idea that American men don't place a high value on their mate having some smarts.

In a 2012 New York Times piece, writer Stephanie Coontz remarked, "Postwar dating manuals advised women to 'play dumb' to catch a man—and 40 percent of college women in one survey said they actually did so. As one guidebook put it: 'Warning…. Be careful not to seem smarter than your man.' If you hide your intelligence, another promised, 'You'll soon become the little woman to be pooh-poohed, patronized and wed.'"

My client was quoting a dating manual that was printed half a century ago, and didn't even know it.

The truth? It's actually sexy when a guy sees you as successful and smart because:

· Your passion is sexy. The fact that you're successful shows that you're driven, motivated, and tapped into something. Passion in life translates into passion…ahem…in other areas.

· It's a lot of pressure for a man to think you're going to rely on him for everything monetarily, emotionally, and otherwise. Even though a number of men like to provide, a man wants to know he's with a healthy and confident woman who isn't relying on him to "complete" her.

· Some men are threatened by a woman who appears to have her life together more than they do. But do you really want to date those men?

But while your success may not actually intimidate a potential date, successful women may scare good men away because:

· In some cases, very successful people show little to no vulnerability. Most dudes don't want to marry a robot.

· Nobody likes a know-itall. A successful woman who puts down everything a guy says or does and corrects him (and the people around her) endlessly won't be attractive. To anybody.

· Some women who have been competing with men in the job market for years have had to develop a thick skin, and sometimes they forget to leave that aggressive attitude at the office. That's not to say a woman should be as demure and delicate as a flower, but she shouldn't lose her femininity just because she has to play tough at work.

Perhaps Miranda attracted her suitor not because she was a flight attendant, but because she was more attentive and playful during the speed-dating session. Smart men find smart, successful women sexy—as long as they're also accessible and fun.

This rule reminds me of that scene in Anchorman, the one where Ron Burgundy hears about a female news anchor.

"What?!?! A woman? As an anchor?!?!" Will Ferrell roars, and then knocks over the table in fury.

That scene is funny because it's ridiculous. And this rule is funny because it's ridiculous.

Like many of the rules in this book, it might have had legs in the 70s. In the modern era—and by "the modern era," I mean post-Jimmy Carter administration—the concept of a "successful career woman" isn't some oddball novelty that perplexes men. We go to college with smart and successful women, we work with smart and successful women, and we respect smart and successful women. It's not that complicated.

Yes, there's still the occasional throwback man who wants a nice, docile, pretty doormat who will never challenge him. A real catch, right? Men (just like women) are into attractiveness, and we find success attractive.

And if the woman makes more money than the guy? Usually it's not an issue. I've dated women who have made plenty more than me (as a freelance writer, this isn't that rare). That said, things can get tricky when the woman makes a lot more money. Even in this case, it's not that we're "intimidated," per se, but it creates some tactical, real-world hurdles that we might or might not overcome.

Let's look at a case study.

Brooke is a lawyer. A damn good one—she just made partner. She meets a dude on OkCupid who paints circles for a living. The Circle Painter refuses to paint straight lines—his motto is, "Straight lines are artifice; circles are truth"—so there's limited demand for his work. Brooke suggests they get sushi; the Circle Painter suggests a happy hour with eight-dollar buckets of PBR. Brooke's a good sport, so she does the Pabst, and they have a good time. Date two: the Circle Painter can no longer afford the beer buckets (rough week for circles), so he suggests they take a walk in the park, where he treats her to a hot dog.

Maybe this lasts for a while. But barring a few unlikely scenarios, this relationship is doomed.

Unlikely Scenario 1:

Brooke is totally, 100 percent cool with changing her lifestyle and living like a college student again.

Unlikely Scenario 2:

Brooke is happy to pick up the bill every time they go to nice places, and more improbably, the Circle Painter is happy to let her. (Tangent: Is it silly and irrational that men feel the need to usually pay? Probably. But right or wrong, that silly and irrational mindset exists. It's also silly and irrational that we still use the electoral college, refuse to adopt the metric system, and call the previews—which come before the movie, not after—"trailers.")

Unlikely Scenario 3:

Brooke and the Circle Painter live out a romantic comedy where true love!!! conquers this fiscal barrier.

Unlikely Scenario 4:

The demand for circles skyrockets, and the Circle Painter gets rich.

Things don't look good for Brooke and the Circle Painter. But this is really only an issue when the income gap is so dramatic that it causes a disparity in lifestyles—it's not driven by an intimidation of success.

We like successful women. Thankfully there are lots of them.



A male hippo attracts a female by using his tail to spray her with his feces. While that's perhaps not the most romantic way to pick up, it's one of hundreds of examples in the wild of males trying to secure females' attention in order to mate with them. Male frogs make noise in an effort to elicit the females' response, male house wrens build a nest to attract mates to nest with them, and male turtles show off their strength and compete with other males by stomping their feet and hovering around potential mates.

Any of this male behavior sound familiar?

Baboons are one of the few species in the animal kingdom in which the females initiate mating rituals. If a female baboon is feeling frisky, she simply has to shake her derriere to get some action. (I've seen this baboon-like behavior in bars around town.)

While we can't depend exclusively on the wild to give us insight into our human mating rituals, I do believe there is something instinctual about males pursuing females. However, as with any rule, it's not that clear-cut.

Some men—especially the shy or reserved type—appreciate when a woman takes the lead. And some men simply find it sexy when a woman pursues them.

Thirty-two-year-old Bob admitted, "I love when women pursue. It takes the pressure off of me and shows she's confident!" When I probed and asked Bob if he generally falls hard for women who make most of the advances in courtship, he paused and concluded, "I guess I haven't. But the attention from them is flattering…."

Even though the women Bob's been most attracted to allowed him to pursue them (for the most part), he still needed them to encourage him to do so by being responsive. "There's nothing worse than an icy response when you put yourself out there in dating," he said. "I won't even bother if a woman gives me attitude."

No man will put forth the effort to court a woman who he feels isn't interested. Scratch that. He may still pursue this uninterested woman and work hard to win her over with his charm and wit, but he would much prefer that a woman encourage him to keep pursuing. (Not surprisingly, men aren't big fans of rejection.)

Men are thrilled when a woman indicates interest, reciprocates affection, and acts responsively to their advances. While I do believe it's true that most men want instinctively to pursue women, a caveat to this theory is that women need to encourage the pursuit. If you're too hard to get, most self-confident guys will move on.

Courtship is awkward, exciting, and completely confusing. If it's too straightforward, it loses some of its je ne sais quoi; but if it's a roller-coaster ride full of mixed messages, cold exchanges, and standoffishness, it also doesn't work very well.

I'd be a hypocrite if I instructed you to always wait for a man to pursue you (I don't believe in always or never rules); but if you are generally the pursuer and want your dating luck to change, start by showing subtle interest and then let men make the next moves. These animals may be onto something….

Things you will never hear me say:

"Damn it. The restaurant's giving us a bottle of win…. on the house."

"Well, this sucks. The bank just deposited five thousand dollars in my account."

"Bad news. A hot woman just approached me."

I've never understood this rule. For me the math is simple: I like women, I'm lazy, and I like it when things that I like come to me. If a woman pursues me, I'm down, assuming I'm either attracted to her or really drunk.

Of course, the word pursue is tricky—it can mean lots of different things. In The Rules: Time-Tested Secrets for Capturing the Heart of Mr. Right, Ellen Fein and Sherrie Schneider counsel "Rule 2: Don't Talk to a Man First (and Don't Ask Him to Dance)" and "Rule 3: Don't Stare at Men or Talk Too Much." In fairness, there's a lot to be said for the psychological power of withholding, so let's look at this a little closer. Specifically, there are four sub-rules on how the woman shouldn't pursue a man:

Sub-rule: Don't talk to a man first (and don't ask him to dance)

I like bold women. If she approaches me and initiates contact? Great. There's no part of me that thinks, consciously or subconsciously, Hmmshe's hot.but I would like her more if I had to work harder. It's true that men enjoy the chase, but the chase is not yet over. It's possible for a woman to initiate contact and still maintain a hint of intrigue.

Sub-rule: Don't stare at men or talk too much

In The Rules, this one begins: "Looking at someone first is a dead giveaway of interest. Let him look at you! If he doesn't notice you first, he's probably not interested. Keep walking; someone else will notice you." This cracks me up. If a woman so much as looks at us, we'll get bored and lose interest, moving on to tougher conquests. Really? Plus, here's the thing about guys: we're clueless. What you think of as a BIG SIGNAL might be lost on us completely. Sometimes you need a more aggressive pursuit just to land on our foggy radar.

Sub-rule: The woman shouldn't ask the man out on a date

Look, if I like her, I like her. If she asks me out and I'm into her? Sign me up. This doesn't mean that the woman should pursue or that she must pursue, but if she does, she's not torpedoing our chances. Like all things, of course, this has its limits. Smothering is a turnoff. And then there's this next one, the fourth categor….

Sub-rule: The woman shouldn't approach the man at the bar and say, "Hey, stranger. Let's go home and fuck."

I've never been lucky enough to actually hear a woman say those words. And here's where the rule makes some sense. If it seems too easy, I'll get skeptical, I'll get nervous, and I'll wonder if something's wrong. Quick example: While on OkCupid, a woman messaged me and said, "This might sound forward, but I also live in Brooklyn. Wanna meet up for drinks tonight and have some fun?" Maybe it's hypocritical, maybe it's sexist, and maybe it contradicts my own philosophy, but it triggered my Spidey Sense. I didn't bite. Because you know what? If the bank deposits five thousand dollars into my account, there's probably something wrong with the transaction, and I'd be a sucker to accept it blindly.

Table of Contents

Introduction: On Rules ix

Chapter 1 The Dating Mind-Field 1

You're intimidating to men because you're too successful 2

Always let the man pursue 7

You find love when you're not looking 12

Don't be too picky 17

Men love bitches / nice guys finish last 21

Expect love at first sight 26

Chapter 2 The First Date 31

Never sleep with him on the first date 32

Always let the man pay 42

Wear a dress (and heels) on the first date 47

Go to dinner on the first date 52

Never talk about politics or religion on the first date 57

Make a perfect first impression 62

Chapter 3 Men You Shouldn't Date 68

Never date a co-worker 69

Date someone age appropriate 74

Long-distance relationships don't work 79

Men and women can't be friends 85

Find a man who makes more money than you 92

Chapter 4 Digital Dating 100

Online dating is only for losers 101

Never friend a crush on Facebook 108

If he's into you, he'll call (not text) 115

Always unfriend an ex 124

Chapter 5 Sex 129

Seal the deal with a kiss 130

Bad kisser = Bad chemistry 136

Break it off if the sex is bad 140

Don't talk about "your number" 146

Chapter 6 This Has Potential (Dates 2,3,4ish) 154

Pretend you're busy if you like him 155

"He's just not that into you" 159

Don't date others if you see potential in him 163

Don't date outside your league 167

Opposites attract 171

Expect a Saturday night date 176

Chapter 7 Seeing Someone 179

By now, you should have met his friends and family 180

You can't change him 185

If they don't approve, dump him 189

Spend most of your time together 194

Never say "I love you" first 197

Chapter 8 Breaking Up 203

You need a rebound 211

Don't try to be friends with your ex 215

Take a break 222

Chapter 9 What's Next 229

Don't move in together until you're married 230

Give an ultimatum 235

Conclusion 247

Appendix: Debunking Some Dating Rules for Men 250

Acknowledgments 255

Index 261

About the Authors 269

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It's Okay to Sleep With Him on the First Date: And Every Other Rule of Dating, Debunked 3.4 out of 5 based on 0 ratings. 4 reviews.
Anonymous More than 1 year ago
You're an idiot, mate. It's called a "review" so you can review the book. If you haven't read it, keep your opinions to yourself or post on a forum.
Anonymous More than 1 year ago
I wish this book had been around back in my dating days, years ago before I was married. It would have saved me a lot of heartache and anxiety! This book is well written and I like that there is both a male and female's perspective. P.S. KJ, for what it's worth, you're an idiot for reviewing a book you've never even read, let alone giving it zero stars. I hope everyone else will ignore his weightless review and give this great book a read.
Anonymous More than 1 year ago
-KJ- More than 1 year ago
I haven't read the book, nor am I going to read the book. It is not okay to sleep with a guy on a first date. I have no respect for a woman if she comes close to letting me go there too fast. I don't have any respect for friends who brag about their conquests either. Nor do most guys when the conversation comes up. The question comes down to how you want to be viewed in your relationship. Do you want to be loved and thought about because of you or because of the physical pleasure you provide? Maybe you feel you need to go there because you can't keep a guy or girl interested otherwise. Well, this is a bigger problem with how you handle the date. Are you showing interest in him/her? Are you talking about topics which interest the person? Are you complaining about anything? Sharing too much info? Most of my dates fail because either I or the person I'm out with complain or share too much information. Sorry, but you are not going to get a second date telling me about your doctor being too aggressive cleaning up your uterus. We are not going out again if you tell me how you've been in and out of the doctor for a year. I don't want to know you have daddy issues on date one. I don't want you planning your life with me, even a month out, if we just met. I don't want to know you have problems with your family. Or you don't really have any friends. I want to leave the first date and most of them smiling because I'm lucky enough to meet you and to continue seeing you. Good luck!