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Shrewd Dating Strategies

Many a brave knave gets a bad case of butterfly guts when it comes to popping the question "Will you go out with me?" Why? It's the old salesman's malady, fear of rejection . So many men never ask. No guts, no glory.

Other men, a tad too confident of their own charm and the lady's acceptance, bestow the invitation to spend an evening in their incomparable company too quickly—only to be shocked by her brush-off.

Several years ago, I was at a party and spotted a fabulous specimen of raw male sex appeal. He bore a striking resemblance to a young Jack Nicholson on a good day. I smiled at him, and he smiled back. At that moment, I vowed I was going to meet him. I started conniving. Perhaps I'd try to finagle an introduction from the host of the party. Or maybe I'd cough up a corny line like "Haven't we met before?" I even contemplated the desperate move of waiting until he was seated and then "just happening" to trip and fall into his lap.

As I was ruminating about my options, he walked right up to me and said he'd like me to go to dinner with him the next evening.

My surprised answer? "No, thanks." And I was sincere. It was too much too soon. He didn't know anything about me. How could he have known about my scintillating personality, my incredible uniqueness, my extraordinary acumen, my resplendence, and my rare humility?

And, worse, I didn't know anything about him. He may have looked like Jack Nicholson, but he could have had the nasty habits of Jack the Ripper—or Jack Nicholson in The Shining .

When and How to Ask Her Out

In real estate, a well-known adage is "location, location, location." Well, in asking for a date, it's "timing, timing, timing." When should you ask for milady's company? Let her feel she got a date with you "the old-fashioned way," by earning it." Otherwise, your company is as valued as a screen door on a submarine.

Sometimes, my actress friends are cast in Broadway shows as extras—which is still a great honor. But they are never as excited about the gig if the director just "typecast" them. Being typecast merely means that they look the part. It has nothing to do with their acting ability. And no woman, no matter how beautiful she is, or isn't, wants to feel that you just asked her out because of her looks.

There is a second reason to wait before asking her out. Because a woman is investing an evening of her precious time in you, she wants to know she's going to enjoy it. So, like an actor auditioning for an important producer, give her a bigger sample of you before asking her out.

This does not mean making a laundry list of your good qualities. Nor does it mean airing your dirty laundry concerning your last six failed relationships. It's more along the lines of making natural conversation and letting your wit and intelligence speak for themselves. Try to balance the conversation, revealing yourself a bit more while keeping the focus on her. That gives her the input she needs to make the "go/no go decision."


Since a woman wants to feel she is the recipient of your awe and admiration, as opposed to your lust and lewdness, ask her questions about herself. Then, when she says something especially revealing, show how fascinated you are by what she's saying. That's the time to ask her out. "Oh, you know all about 12th-century dental practices. Gee, that's fascinating! I'd love to continue this discussion say, uh—next Saturday night."


Postscript: Don't reveal too much. A little mystery also fans the flames of passion.

To Her, It's Not a Date; It's an Audition!

Guys, my heart goes out to you. A female, on your first date, misses nothing. I mean nothing . No analyst ever examined a patient's mentality as much as a woman will analyze you on everything you say, everything you do, and everything she thinks you're thinking. She picks up on your every word, your every movement. She scrutinizes how you look and how she assumes you feel, and tries to piece together your life history. When she's got a fix on that, she fantasizes about your future. Does she want to be a part of it? "Long range," "short range," or "fat chance!"

No crashed commercial airliner ever got the scrutiny you're going to get as you innocently sit across the restaurant table happily chatting about this and that. Be on your toes, because now is the time that you are being auditioned to play a leading role in her bedroom. In days gone by, it used to be that a woman had to "feel in love" to go to bed with someone. Now it just has to "feel right."

What makes it "feel right"? Quite simply, if she feels your character is in sync with hers and you make her feel special. You must do this from the first pitch to the bottom of the ninth.

The Proven Best Thing to Do on the First Date

Where you would probably like to go on your first date with her (a football game), where she would like to go (dinner at an upscale restaurant), and where you should go (information pending) for maximum sex appeal are three different places. Sure, you'd probably like the sporting event, because if she turned out to be a dud, you could at least enjoy the game. She'd like the restaurant, because, in addition to a great meal, she'd have the opportunity, during the conversation, to evaluate you as someone who could possibly be part of her future. But if your goal is (as the fact that you're reading this attests) to bed the lass and possibly someday wed the lass, that is not the best choice.

There is compelling evidence that she will be more turned on to you if you place her in a "scary, emotional, or vulnerable" situation. You don't need to lock her in the trunk of your car and tell her you're going to drive it over a cliff. A scary movie will do. Or, if she is a fan of Gregorian chants or heavy metal, an evening of chants or a Metallica concert will qualify as an emotional situation.

Research has shown a strong link between emotional arousal and sexual attraction. Have you ever wondered why, in all the great love stories depicted on the screen, on the stage, and in novels, the lovers or wannabe lovers face a great challenge together? Often, a towering inferno, a jungle of prehistoric beasts, a tornado, or a motley selection of evil forces threatens to tear the couple asunder. Did it ever cross your mind that they might not be lovers, or even want to be, if it weren't for the immense adversity they had to tackle together? I mean, what would be the big deal about Romeo dating Juliet if the Montegues didn't want to kill all the Capulets?

Consider this: More office romances start in workplaces that have atrocious bosses than in offices filled with happy campers. Potential lovers placed in an emotional, stirring, or vulnerable situation are more apt to be attracted to each other because "It's you and me, Babe, against this big bad boss."

At least one study, reported upon in the Journal of Personality and Social Psychology and called "Evidence for Heightened Sexual Attraction Under Conditions of High Anxiety," proved the connection between fear and sexual attraction. 56 Subjects who had volunteered for the study (without knowing what it involved) were brought into a laboratory where a male and a female researcher were sitting. The researchers told half the volunteers they were going to receive a very severe shock. The other half were told that they would receive an extremely mild shock.

Each subject was then introduced to another researcher of the opposite sex who stayed for a few minutes and then left. After his or her departure, the researcher of the same sex asked the subject's opinion of the person who just left. The results? The girls who sat quaking in their shoes and shuddering about the severe shock to come rated the guy who just left as much sexier than did the girls who were going to get the mild shock.

Studies like these show that when a woman is feeling a strong emotion, such as fear, she's more apt to be turned on to you. Why do women experience these whacko reactions? As is the case with most whacko reactions, the answer goes back to drugs—in this case phenylethylamine, or PEA, the naturally produced drug discussed earlier. Fear produces the same high that shoots through our veins in the early stages of infatuation.


Obviously you're not going to tell the lady she's going to receive a severe shock by dropping hot candle wax on her nipples (unless she's one of those kinky gals who's into that sort of thing). But science tells us that if your first experience together is stirring, your date will transfer the strong emotions to you.

Physical activities that get you moving around are also good. Physical activities that get you moving around and touching each other are even better. Unless you'd look like a cow on ice, dancing is a good choice.


Barring the physical, go for something that's emotionally exciting for her. Does she love opera? If so take her to the opera. (How about Madame Butterfly? That leaves everybody sobbing at the end.) Does she love movies? Take her to a movie. (Have you seen any good horror films lately?) Does she like amusement parks? Take her to the amusement park (and be sure to go on the death-defying, killer-diller, triple-twist roller coaster).

Stamping Out Piggy Male Manners

Most men are a little fuzzy about manners. It comes with the territory. I can hear you now. You're grousing, "Criminy, I answered an ad saying, 'What if you never heard the word no from a woman again?' and you're going to tell me I have to extend my pinky when drinking from a cup?"

No, of course not. There's no need to sweat the small stuff, but you want to eliminate the gross fouls that turn female umpires off—such as talking with your mouth full, using the wrong fork, picking a piece of painful roast beef out of your back tooth with the edge of a sweet 'n low packet, and forcing your way onto the bus before the people get off—and then, to top it off, not giving the little old lady your seat. Honest, the good manners you exhibit on a date rank right up there with great sexual technique.

A few hints: After parking in the restaurant parking lot, swiftly leap around to her side of the car, open the door, and extend your hand to help her out. She'll be impressed.

As you cross the street, offer her your arm, lest she, wobbling in her painful little shoes, should trip. For that matter, even if she's wearing sneakers and says, "Ah, you don't need to do that," she'll secretly appreciate it.

Oops, you spot a little doggie-doo-doo by the curb? Nonchalantly steer milady's path so her tootsies don't get soiled. (Do not then bring your gallant deed to her attention by saying, "Boy, I sure saved you from that shit, huh?") As you enter the restaurant, you, of course, hold the door for her.

"Nice," she'll think. As you head for your table, pull her chair out before seating yourself. Now, knowing you're an all-class dude, she'll start having X-rated thoughts, such as whether you're a "boxer shorts" or a "briefs" man.

The lady will probably be carrying a purse. If you want to know how you're doing so far, check to see if she instinctively moves it to the side you're not walking on so there is no obstruction between the two of you. If she moves it, she likes you. If she leaves it between you, it's as if she's using it for protection.

Now you're at the restaurant. As I mentioned before, if the maitre d' isn't there to do it, pull the chair out for her. When it comes time to order, you should ask her what she would like for dinner and then give both your orders to the waiter. She'll be purring. And if you say, "the lady will have" (as opposed to "she will have), she'll begin imagining peeling either your boxer shorts or your briefs off with her teeth.

I kid you not. Manners matter.

The All-important Dinner Date

No matter what you do on your first date with her, you're eventually going to wind up putting the feedbag on together. Where should you take her for this first ceremonial breaking of bread?

Alas, what impressionable creatures we women are! Why we get upset when you mentally undress us is beyond my comprehension. You are, in a sense, looking at the real us, without the trappings. Women are much more impressed by a man's clothes than you are by ours, and we are also impressed (or depressed) by the atmosphere of the places you take us.

Before you make a decision, let me clear up one misconception. You may think you're being nice by asking her where she'd like to go, letting her decide. She may even enjoy choosing the place. But there are two big negatives. First and worst, it makes you look androgynous. Take charge, man. You make the reservations—and don't forget to confirm them! It will make you look real bad to her if your table isn't ready on time just because Robert DiNiro made a reservation right after you did and you got aced. Better yet, try to "be known" to the maitre d' so he welcomes you by name. (It's astounding what good memories a maitre d' will develop if your handshake was padded with a little green the last time you were there.)

Now, two factors affect your choice of restaurant. The first is your realization of how superficial a woman can be in her judgments. In fact, researchers showed pictures of men to a group of women. 57 Sometimes, the men were photographed in lavish, luxuriant, (read "rich") rooms. Other times, the cameras showed them in dilapidated, dumpy settings. To isolate the setting as the variable, in this particular study, the pictures were of the very same men dressed in precisely the same way.

It is with some embarrassment that I tell you that the men in the lavish looking house were judged more attractive than the men in the dumpy house. Women will definitely transfer their feelings about whatever setting you are in to their feelings about you.

One of the advantageous things about sitting across the table from a woman is that you can get a real good read on how much she likes you. Here, Jade, a very sophisticated woman, is using a subliminal sex signal on you.

Well, it's not too subtle, is it?

Like the sirens who lured sailors to their death by their beautiful singing, some women will lure men across the room to talk to them by their sensuously caressing a glass or cylindrical object like a pen.

Undercover Sex Signal #23: THE SEXY PET

If you see a woman across the room looking at you and not smiling, you might not think she wants you to approach. But if you take careful note of her hands, you may see she is running a finger around her wineglass. It is not out of boredom. She might even be imagining that she is caressing you. In this picture, jade has chosen to caress her glass with her pointing finger, figuring that her middle finger or ring finger would be just too obvious.

At other times, a woman uses the sexy pet by fondling a pen suggestively or running her fingers up and down the stem of a wineglass.

If you are already conversing with a woman, it is likely to be a contrived move when she slowly and seductively runs her finger around the rim or up and down the stem of a glass when talking with you. Almost any object can be used suggestively—a pen, a utensil, a swizzle stick, etc.

Taking this deficit in the female psyche—judging you by the place you take her—into account, take her to an eatery that reflects the personality you'd like to project. In fact, if the lady is really worth it, take her to the most upscale restaurant in that genre that you can find, but not one where you're going to have to worry about which of six forks to choose from.

Do you like to be thought of as artistic? Take her to a restaurant where (relatively rich) artists go. Do you want her to think of you as a successful businessman? Take her to a restaurant where (relatively rich) businessmen go. Do you want her to think of you as a cool dude? Take her to a restaurant where (relatively rich) cool dudes go. Would you like her to think of you as a hippie? Take her to a restaurant where (relatively rich) hippies go.

Ok, ok, so that's an oxymoron, but you get the idea.

There is one exception. Even if you want her to think of you as a jock, do not take her to a sports bar—unless of course, she's used to hanging out there anyway. In which case, she's a rarity; so make her a keeper.

If the lass has class, you should take her to a really fine dining establishment the first time you go out with her. Since, however, the tiny provisions and exorbitant prices at some restaurants will leave you both hungry and broke, you don't want her to become accustomed to that style. On your next date, therefore, avoid any mention of where she'd like to go.

She might already be suffering delusions that other expensive restaurants are going to become among her regular haunts. You may handle such a distressing situation in this manner. Don't just choose an inexpensive "normal" restaurant the next time. Instead, take her to some charming (read "inexpensive") restaurant serving ethnic cuisine. Tell her you've been reading about, say, Vietnamese food, and can't wait to try it. (The average dinner price in all the Vietnamese restaurants I know is in the single digits.)

Then for date three, back to Les Expensivo. Next date El Cheapo. And soon your eclectic taste in food will even include a Fridays and Taco Bell, in time to make the movie. But, by then, the two of you should be making it, and the choice of restaurant will probably be the least of your problems.


Bonus hint: Try to get her to order a chocolate dessert. Some say there is a minor link between sexual arousal and chocolate. More accurate is "the chocolate link." If she's watching her weight but lets herself go and pigs out on a high-calorie monster, it means she's feeling pretty loose.


Incidentally, there is a strong argument for taking her to a quiet restaurant that is darkly lit. Women aren't the only one's who look better in candlelight. Men also look more alluring, more mysterious. Their eyes get sexier due to the pupils' opening up in the darkness. (Bedroom eyes, remember?)

Now, all this talk of restaurants brings me to two oft-asked questions: "Should I let her pay for the dinner?" My short answer is "No." "How about letting her leave the tip?" many men ask. Again, the answer is "No." Say it however you like. Whether it's the tough guy's, "Your money's no good in here, Babe" or the more refined "How kind of you to offer, but I wouldn't hear of it" (or anything in between), she'll appreciate it.

I know such an approach may be viewed by some as unjust, inequitable, and antiquated. It may even run counter to everything the lady says she prefers. But you already know that every woman has at least a bit of the romantic in her, a feeling that "someday my prince will come along on a great white horse, he'll scoop me up, and we'll ride off into the sunset together and live happily ever after." And what kind of a prince ever lets a woman pay. Or even go dutch? (On later dates, after you're friends and lovers, it's another matter. Even then, however, pretend to be a little "disturbed" that she's picking up the check.)

Kissing, Calling, and Other Follow-up Strategies

It's hard to believe that the male of the same species that planted the American flag on the moon still wonders if he should plant a kiss on a woman's lips on the first date. Here's where everything you've learned up to this point comes into play. Have you kept count of the many undercover sex signals she's been hurling your way? Has she been smiling? Has she been leaning in toward you? Has she turned her palms toward you? Has she brushed her hair back while talking with you? Has she run a finger around a glass? Has she put a swizzle stick in her mouth while listening to you? Those are just six signs. There are 19 other nonverbal cues that show she'd like you to take her in your arms. Soon, reading them will become second nature.

Otherwise brilliant and accomplished American males are flummoxed by questions like "How long should I wait before calling her again?" and "Should I tell her at the end of the first date that I'd like to see her again?" Let's say you see her Saturday night. You like her—a lot. You want to see her again the following Saturday. So you're wondering about your best call-back strategy.

Pieced together from conversations I've had with the many hundreds of women in my classes, here are the options and what each is likely to make her think.

Should I call later the same night? Unless she left some life-support medicine in your car, it makes you look too lonely and anxious.

Should I call Sunday? If you do, you risk looking like you think she's the only game in town for you.

Should I call Monday? Nah, that's being too predictable

Should I call Tuesday? It's not the most tactical strategy. Let her get a tad concerned.

Should I call Wednesday? By that time, she'll be getting really worried that you might not call.

The most tactical time to call is late Wednesday afternoon at work, or at her home if you really do want to see her the following week. (At one shameful time in our history, all females were reading a ridiculous book called The Rules , a book that set relationships back half a century. It said, "Don't accept a date for Saturday night later than Wednesday." What a travesty!)


A super-cool move: Call her office Saturday night after your date and leave a voice-mail message saying, "I had a great time—I'll call you this week." Then don't call until Thursday. If she likes you already, that'll drive her nuts over you.


Now, even better, is to call her on Thursday, not for the up coming weekend, but for the following weekend. That will keep her guessing and yet still interested. (Not to mention it permits you to juggle two ladies at the same time. I call it "flextime" dating.)