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Video: Why ladies should ‘Always Hit on the Wingman’

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    >>> on today's relationships, the male perspective. jake is the longest running dating advice column in america. the authors have changed but the advice is timeless. there is a new book from jake called "always hit on the wingman" and nine secret rules for getting the love life you want. cindy, good morning.

    >> good morning.

    >> we have to put him in silhouette if jake were here.

    >> he's fully anonymous. always has been.

    >> p this this is a long-running column. does the advice stand the test of time?

    >> the column started in 1956 . some things are clearly outdated like references to white gloves but the basic advice men have been giving women is be yourself. be a little bit more confident in a relationship than you would naturally be.

    >> before we get to jake 's advice let's find out more about jake . what's the profile? he's got to be single.

    >> he's got to be single. once he's serious with a woman, sorry, we have to fire him. he should be writing about what's going on in the mind of a man who's out there dating.

    >> we have a new jake that writes for glamour. the jake that wrote the book is married now to --

    >> orange blossom , a reader of the column. while he was writing he fell in love , dated and broke up with, much to the dismay of readers orange blossom who he nicknamed because of her perfume. they are now happily married.

    >> i love that. jake says to get your flirt on even in a relationship. be flirting all around.

    >> yeah. listen, within reason. if you have a partner who will have a problem with it, maybe hold back a little bit. his advice is essentially always hit on the wingman. you're in a situation where there is a guy you want to talk to. that can be intimidating. flirt with the guy he's with with. it's the same principle of you have the best job interview for the job you really don't want. this is a dream job interview with the recruiter for the job you do want standing over your shoulder watching. be more relaxed.

    >> it also exudes confidence which moves into the next tip which is love your body.

    >> this is a message that's come up decade after decade from jakes. men love women 's bodies, period. they like big ones , small ones, doesn't matter. every time you complain about how you look or point out a flaw you're telling him he's wrong to enjoy you. don't do that.

    >> he's saying to be confident in yourself. don't be constantly reminding your significant other of our imperfections.

    >> no reason to do it.

    >> save it for your girlfriends. and embrace your feminine side .

    >> there is a trend of women feeling like i have to be one of the guys, completely up on sports, know about the inside fly rule. do all the things guys do. great if you are into it, go for it. don't feel you have to understand or know all about a man's interests. he wants to talk to you about it and have you interested. you don't have to know the details. the message from jake is to yourself. men like women who like sports, women who don't like sports. they just like women .

    >> jake says to keep your options open. if you ever dating don't rush into being exclusive.

    >> he says women should start dating other people longer than they think they should. out sounds counterintuitive. you find the one you're so relieved to settle down. he says unless you are 100% sure this guy is giving you everything you want and need in a long term relationship why close yourself off to every other guy out there? if you prioritize your needs a guy respects them as well.

    >> and he said to beware of the buddy trap mixing romance and friendship.

    >> friendship is the basis for a good long term marriage but you have to keep some things private; some things to yourself. keep your own interests. be your own person.

    >> keep the mystery alive. cindy leive from glamour, thank you.

TODAY books
updated 1/23/2012 6:29:30 PM ET 2012-01-23T23:29:30

As the male dating columnist for Glamour magazine, the mysterious Jake has been providing tantalizing insight into the way men think for the magazine’s readers for years. At last, Jake has amassed this wisdom into a strategic dating guide, “Always Hit on the Wingman… and 9 Other Secret Rules for Getting the Love Life You Want.” Here’s an excerpt.

Rule #1 Always Hit on the Wingman: It’s the World’s Best — and Most Empowering — Flirting Technique

So, where to start? How about at the very beginning — the moment you lay eyes on a man you like, and want him to lay eyes back on you?

There you are, out for the night, in your dry-clean-only jeans, wearing perfume, looking hot, smelling edible. You’ve done and redone your hair so it looks the right kind of messy. And you see this guy you wouldn’t mind talking to. Say it’s a guy you’ve met once or twice in passing, and thought, Why isn’t he at the parties I go to? But here you are, at a party, and so is he. What’s the natural thing to do? Yeah, the natural thing to do is freeze.

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Seriously. It’s natural. Don’t feel bad about it. He’s probably a little terrified too. So don’t let a little case of the nerves stop you from walking across the room and striking up a conversation. How, you ask? Hang on for a little story about the world’s best first-few-minutes flirting technique. It’s so good that it’s actually more of a flirting philosophy—one you should keep on using at every stage of your relationship, forever!

The year was 2000. I was with my friend Mark at a house party. The lights were low. The necklines were lower. We were feeling all self-conscious the way men tend to when they roll into a place together. You know what I’m talking about: Two guys walk into a bar or a party like some kind of lady-molesting team. They try to appear laid-back, or at least not desperate, as they awkwardly suck down their drinks, ogle women and don’t talk to each other.

Video: Why ladies should ‘Always Hit on the Wingman’ (on this page)

These lame and transparent characters are called wingmen. Some people think the wingman is the second fiddle. Not true. If two single, straight guys are out together, they’re both wingmen.

Anyway, Mark was my wingman on this night, and I was his. I came back from the bathroom and saw a gorgeous woman chatting him up. I’d noticed her when she’d walked in, but I had quickly become distracted by another woman at the party whom I’d slept with once—and never called after. Should I do it again and hate myself? Not do it again and hate myself? I was too absorbed in this internal debate to actually put all that aside and approach someone new.

Ms. Gorgeous had blond, almost freakishly long hair. If you were a hair fetishist and you saw her at this party, you’d have had some kind of aneurysm. And there she was, talking to my wingman.

“She’s from Delaware,” Mark filled me in.

“You don’t say,” I replied.

“Look at that hair! Wouldn’t you think she should be from Sweden or something? Or at least Minnesota?”

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Ms. Gorgeous laughed and put a hand on Mark’s arm. I still remember the dread I felt when I saw that hand touch his arm. You know a flirty touch when you see one. With that little brush of her long fingers, she became at once more desirable and more unattainable. I figured that since she was after Mark—and I didn’t have a chance with her—I would at least try to make her laugh. And I spent the next half hour in that attempt, not wanting to piss off Mark, but curious whether she wanted me to stick around. Eventually, when I went to the bar area to get another drink, Ms. Gorgeous said she’d come with me. Yes! I was thinking. I got her! Little did I know it was she who’d gotten me.

Flash-forward three months to my bedroom: Ms. Gorgeous and I are a couple and will be for another glorious and tumultuous six months. We are naked in bed, eating take-out sushi and talking about the night we met. She looks at me slyly and says, “You know, I never wanted to talk to Mark in the first place. I was just trying to get to you.”

“Shut the f*** up!” I say.

“Are you kidding me that you didn’t know that?”

“All these months I thought you were harboring some unresolved attraction to Mark!” I say. “And all this time I’ve actually felt guilty around Mark, like I stole you from him.”

“It’s one of the greatest tricks of all time,” says Ms. Gorgeous. “Always hit on the wingman.”

Always hit on the wingman. It was so simple, so perfectly tailored to men’s innate competitiveness, so…genius! Ms. Gorgeous was right: The Wingman Technique is probably one of the most effective seduction tactics ever. Not convinced? Here are four reasons why:

1) Flirting works best when it feels effortless.
Imagine the man of your dreams hanging out at a party near the beer cooler with his friend Mark (work with me, it’s an exercise). Now imagine you have to go up and talk to him. How do you feel? Like you’re about to go skydiving only without that little backpack that has the parachute in it? Of course. You’re terrified. And damn it, now that you’ve let the moment pass, he’s talking to that chick in the Uggs. Or worse, he’s getting bored and making his way to the door.

Now imagine that Mr. Dreamboat Dude isn’t there. It’s just Mark. Mark in the mock turtleneck, with the bad sideburns. If you were forced to go talk to him, would you be nervous? I didn’t think so.

Think about it like a job interview. There’s a truism that your best interview is always for the job you don’t want. Flirting is the same way. Have you ever noticed how effortlessly cute you are when you’re talking to someone you’re not attracted to? How you’re always getting the wrong guy to eat out of your hand? The best part of the Wingman Technique is that you get to be effortlessly cute and confident and relaxed in front of the guy you actually like.

Hitting on the wingman is like interviewing for the job that you don’t want, with a recruiter for your dream job standing right there, very impressed.

Big caveat: There’s a difference between flirting and coming on like a starved velociraptor. I bet you can guess which side of the fence to stay on. Go easy on it. Be subtle. If you go overboard, you’ll seem desperate—or possibly nuts.

2) Men crave what they don’t have.
Here’s the second reason the Wingman Technique works. I call it the Cheeseburger Principle: When a guy sees his friend eating a cheeseburger, he instantly becomes hungry for a cheeseburger. Even if he just ate. Even if he’s trying really hard to be a vegetarian. Watching a woman flirt with his friend has the same effect. It makes a guy realize she is…no, not a piece of meat, but yummy looking, and worth getting hungry for.

3) Competition makes the heart beat harder.
This point is an extension of the Cheeseburger Principle: If men think something—or someone—is too easily attained, we worry we may be too good for it. Just like every other bad habit we have, this one surely goes back to our caveman days, when “getting the girl” meant chasing her other suitor 16 miles, pushing him down a hill and rendering him unconscious with a good bonk to the head. As exhilarating as it is to get close to a beautiful woman, it’s even more of a rush if we have to (figuratively) bonk someone over the head to claim that spot. More centered, together, enlightened dudes may be above this way of thinking, but sadly, most men aren’t there yet. So let your crush see you as a challenge to win over. When a guy gets the chance to talk to you, he should feel like it’s a big opportunity.

4) You never know, the wingman could actually be your man.
I’ll talk more about this in Chapter Four, but for now, suffice it to say that sometimes the guy who doesn’t knock your socks off the first time you lay eyes on him is the real catch.

Bottom line: This isn’t really about the wingman. It’s about power. Remember when I said hitting on the wingman is a flirting philosophy? Well, here’s that whole theory in a nutshell: When you hit on the wingman, you’re in control of the situation.


From ALWAYS HIT ON THE WINGMAN…and 9 Other Secret Rules for Getting the Love Life You Want by Jake. Copyright 2012 Conde Nast. Published by Hyperion. Available wherever books are sold. All Rights Reserved.

© 2012 MSNBC Interactive


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