Why You Should Always Hit On The Wingman

Looking for foolproof advice to help you meet, date (and most importantly, keep) the right man? Heed these tips from Jake, Glamour magazine’s relationship guru.

By Chelsea Kaplan

eed a little guidance when it comes to men? Forget seeking out the counsel of your best friend, a female coworker or mom — sometimes, the best person to offer you male-oriented advice is another man. And what better man than Jake, Glamour magazine’s relationship columnist and author of the new book, Always Hit on the Wingman ...and 9 Other Secret Rules for Getting the Love Life You Want. For more than 50 years, this columnist
If you’re no supermodel, there’s no need to fret, sisters.
has served as Glamour’s dating adviser, providing insight and advice for millions of American women. Below, find a sampling of Jake’s can’t-fail tips on how to get the guy — and keep him!

Tip #1: Always hit on the wingman
According to Jake, a woman is generally at her flirting “best” (read: relaxed, calm, easygoing) when she’s not chatting up someone whom she thinks may be Mr. Right. Therefore, when you’re ready to approach your crush, Jake recommends that you employ his “Wingman Technique.” Instead of hitting on your perceived Mr. Right, try flirting with his nice but so-not-your-type buddy — right in front of him. “The Wingman Technique is probably one of the most effective seduction tactics ever,” says Jake. “Think about it like a job interview; there’s a truism that your best interview is always for the job you don’t want. Well, flirting is the same way. When you hit on his pal in front of him, you’ll be effortlessly cute, confident and relaxed in front of the guy you actually like!” Essentially, it’s like interviewing for the job you don’t want — while the recruiter for your dream job is standing right in front of you.

Tip #2: Love your body
If you’re no supermodel, there’s no need to fret, sisters. “The idea that the ideal woman exists on the cover of a Victoria’s Secret catalogue is similar to the idea that the ideal man is on the cover of a romance novel; it’s wrong, and we know better,” Jake asserts. Women might fantasize about a man with bulging muscles and a castle somewhere in Europe, but it’s just that: a fantasy, Jake says, and that’s how the whole “supermodel” thing is for men, too. In turn, Jake says that for men, there is absolutely nothing sexier than a woman who feels good about her body and isn’t intimidated by the ludicrous standards established by things like (heavily airbrushed) men’s magazine photo shoots. So quit comparing yourself to Brazilian supermodels, already (and to be fair, quit comparing every guy to Tom Brady).

Tip #3: Beware of falling into the “buddy trap”
Anyone who has been married for a long time will tell you that a strong friendship is the key to his or her relationship’s success. However, in the early stages of a relationship, Jake says that in no way do you want your boyfriend to see you as one of his buddies. “Avoid [engaging in] ‘buddy behaviors,’ like getting wasted together, calling him when you’re bored, or working out together — it’s never as hot as it sounds,” Jake cautions. Preserve some air of mystique; don’t use the bathroom with the door open, and let him know that he shouldn’t do it, either. And bear in mind just how important it is to keep pursuing your own interests. Don’t try to join his weekly basketball game, and no, he’s not welcome to watch True Blood with you and your friends on girls’ night. Instead, Jake recommends finding new things the two of you can do and learn together — or if you’re legitimately interested in basketball, ask him for a private lesson. “The point is, don’t try too hard to unite; you want to stay your own person and be the one who he wants to get to know more and more about,” Jake explains.

Tip #4: Keep dating other people longer than you think you should
Keeping your options open does just that: it keeps your options open. And while that may sound ridiculously simple, Jake feels that he can’t emphasize this particular nugget of
A real gentleman doesn’t go fishing for credit or applause.
advice strongly enough. “When you’re dating, be more selfish,” he says. “Always think about what you’re getting — physically and emotionally — from a guy before you close the window to other potential relationships.” Doing so will make you feel more empowered and less like a wishful monogamist, because it will put your own relationship in greater perspective and frame him (blatantly or not) as the pursuer. Plus, remaining in the dating pool will also show your guy what he’s potentially missing. (Not sure you want to rent that apartment? Well, how do you feel about it now that you know there are other interested parties?) And when is it the right time to commit to someone? Jake says that he feels there’s no universal point where you should stop dating around and focus on just one man, but generally speaking, it’s when you’ve both decided that this is the relationship you want above all others.

Tip #5: Make your man think that making a commitment is his idea
At the risk of sounding like Captain Obvious, Jake claims that, generally speaking, men care less about commitment than women do. Less obvious is his explanation of why this happens: “A lot of times, it’s how we exert power in relationships. If we’re uneasy about moving in, calling you our girlfriend, popping the question, etc., and we know it’s what you want, we hold all the cards. Forcing the issue — or worse, throwing down an ultimatum — usually makes us dig in our heels; we’re guys, after all, and we like to feel powerful.” Instead, Jake advises proceeding with your life just as you would if he wasn’t in the picture; so, take that job, buy that apartment, and then suggest moving things in a more serious direction without actually saying it to him outright. For example, try: “I want to make sure you’re comfortable with where our relationship is” (but don’t say, “Do you think you’d like a big wedding or a small wedding?”). “By making the idea of commitment a no-brainer for him, he’ll get there on his own,” Jake says.

Tip #6: Enter into any cohabitation arrangement with caution
According to Jake, choosing to move in with your man is a step that must never be entered into nonchalantly. Before you take the cohabitation plunge, make sure you know pretty much everything you can about this person — his financial info, family stuff, past relationships, job history, etc., advises Jake. Before moving in together, make sure that you both share a mutual understanding that it’s OK to still be independent; “You don’t need to do, say, and make everything together!” Jake says. He also advises taking a cohabitation “test drive” of sorts before finalizing your plans. “Trade keys first and experience what it’s like to lose that sense of independence and propriety of your space,” he suggests. “Very few couples later in life bemoan the fact that they took too long to move in together. It’s a decision people rush into and it ruins otherwise great, potentially successful relationships.”

Tip #7: Find a man who shows you real chivalry
Being chivalrous is a matter of perspective; it can range from opening your car door to asking your dad for your hand in marriage. Regardless of whether your guy is a bond trader or a member of a biker gang, Jake insists that he must be motivated to find ways to make you feel special. “At the end of the day, chivalry is really just him going out of his way to show you respect,” Jake explains, advising that you first consider the degree to which he’s being chivalrous when evaluating your courtship — especially if something he does makes you a little uneasy as a “modern” woman. “Ask yourself: Is he doing this out of deference to me, or is he doing it for himself?” Jake suggests. “Here’s a tip: A real gentleman doesn’t go fishing for credit or applause.”

When DC-based journalist Chelsea Kaplan isn’t helping you solve your relationship problems, she’s making jewelry. Check it out at
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