Dating Tips for Confident, Assertive Men: Learning from Rebecca Watson

How men can become confident and assertive while dating.

Posted Jul 12, 2011

Welcome back to The Attraction Doctor

One of my fellow PT bloggers, Dr. Kaufman, recently wrote an article about "what shy, geeky, nice guys can learn from the Rebecca Watson incident". For those who do not know, Rebecca Watson is a feminist skeptic who recently blogged about an experience she had while speaking at a conference in Ireland. Apparently, a fellow conference attendant attempted to ask her out in an elevator for coffee at 4am (in a shy, "geeky" manner). Watson was made uncomfortable by the situation, created a vlog post discussing it, and that post ignited a heated debate (which even drew in Richard Dawkins, many feminist rebuttals, and spiraled out of control).

The resulting "debate" has left many a man scratching his head and asking the questions, "how and when is it ok to ask a woman out"? Clearly, men don't want to become the object of Internet ridicule or feminist scorn. In an initial attempt to address this confusion, Dr. Kaufman wrote his article and provided some points for men. I enjoyed his points. However, upon further reflection, I decided my personal advice differs a bit from his thoughts.

My perspective encourages men to be active and assertive. In fact, it is my opinion (and one of the principles of my approach) that all individuals are entitled to be assertive about their needs, wants, and desires. Both men and women should respect each other's boundaries, but also be free to pursue their interests. We should be looking for the win-win at all times, without stifling each other, or censoring the other group. So, in this instance, while I believe women's needs for safety and comfort are very important, I also hold that they can be respected in ways that do not require men to renounce their masculinity, confidence, goals, aspirations, or assertiveness.

Therefore, this advice is for men who would like to grow to be "confident, assertive, and masculine" above-and-beyond simply "shy, geeky, and nice" - and it offers a few additions to the points put forth by Dr. Kaufman.

7 Tips for Men

1) Instill Trust and Comfort

Go beyond "not being creepy". Ideally, look for situations where a woman is most comfortable and approach her there. Learn to be comfortable wherever she is comfortable (read my post HERE if you get approach anxiety).

In reality though, she is most likely taking her cues from you. Even an elevator can be made comfortable with the right body language. Leaning back, giving her space, with a calm demeanor works wonders to instill comfort in any situation (see HERE for more on body language). trust = no agreement = no date.

2) Assume Initial Interest, Then Look for Indicators

You can most certainly assume you deserve her interest. After all, you are a great guy, who has every right to think well of himself. This doesn't mean that she is going to jump into bed with you right away...but certainly assuming respect, courtesy, and curiosity isn't out of the question. This reasonable assumption gives you the courage and confidence to move the interaction forward.

After that, it does pay to look for indicators of her interest. This provides the "feedback" about how your approach is going. Learn body language. Learn to read whether she is "comfortable" and "attracted" to you. Basically, if her body language is open, her feet are pointed towards you, she's smiling, making eye contact, and continuing the conversation...continue to assume interest and move forward. Ask for what you want until the body language changes. Even when it does, that doesn't mean that her interest is "gone", but rather that you need to make her feel more comfortable or interested for her to move forward. Once you do, and the positive body language resumes, continue forward...

It is important to remember though, that an indicator of her interest isn't the same as waiting for permission. A strong, confident man does not wait for "permission" to approach a woman. He has a belief that her life will probably be better for having known him (at least until he receives feedback otherwise). So, assume interest and approach, until you have a clear signal that she isn't interested. If she does signal disinterest, however, respect her wishes and leave. While you can assume initial are not "entitled" to her compliance. Find someone else at that point.

3) Due to Safety and Pleasure Concerns, Women Are Less Likely to Hop in the Sack with Strangers

The Conley (2011) study noted by Dr. Kaufman actually has TWO main points. The conclusions point to the idea that women need to feel that a casual sexual experience will both be safe and pleasurable for them to consider it (see my discussion of that article and tips HERE and HERE). A guy who focuses solely on safety will not be seen as attractive or pleasurable. In fact, a little mystery and danger builds attraction (think women's sexual attraction to "bad boys"). Something has to get the adrenaline, endorphins, and dopamine pumping. Asking them about their favorite color may make them feel safe and comfy...but it also makes you feel like a brother.

That is why courtship is a balance. Too little comfort and trust...and you're a "creep". Too much comfort without any masculine assertiveness...and you're "just a friend". Women need both safety and the promise of pleasure to be sexually interested. So, make sure you eventually lean in, make good eye contact, take up a bit more space, smile, and ask her out confidently (see HERE again for more).

Along these lines, it is also important that you don't have any guilt over your feelings as a man. While you DON'T have a right to ever force a woman to be sexual, you have every right to be a sexual being, and desire sex with her. That isn't something to be ashamed of wanting. In fact, being comfortable with your sexuality and congruent with it behaviorally sends a message to women that, when both of you decide and agree, sex may be pleasurable. Women though, just don't want the interaction to be ALL about sex. So, get to know them as people too (which builds trust). See how it all relates :)

4) Build Some Sort of Rapport and Attraction First

Here again, it is a balancing act. Yes, you need rapport. But, you're not adding her up as a "buddy" or colleague, you're getting a date. So, just chatting about "safe" common interests isn't going to attract her. At the very least, a little challenge or teasing is required. Disagree with her on a point you actually disagree with. Start a friendly debate. Playfully make fun of her taste in music. Be a bit of a "challenge".

Overall, you want to be your own person...not a sycophant. Men (and women) with their own thoughts, ideas, unique opinions, and willpower are attractive. So, feel free to break rapport, ask for what you want, and be assertive. If you need help putting a little "SPICE" into your conversation, look HERE and HERE. If you need help promoting their good feelings or behavior, look HERE. Also, remember to have them invest in you back (see HERE). You're worth it too ;)

5) Stay Relaxed

I completely agree with this one. As Dr. Kaufman says, "Best approach to make a stranger feel comfortable, especially in an enclosed space: be calm, cool, and collected." You are always leading the interaction. Your nonverbal communication is providing your partner with information about how to interpret the situation. We ALL look to others constantly to decide how to evaluate a situation. So, if you are calm, then they will be calm. If you're nervous, then you're going to freak them out. That was probably 90% of poor Ms. Watson's reaction right there. He may have meant no harm, but his own "anxiety" of asking her out was contagious. As a result, she felt threatened, irritated, or annoyed.

Stay cool...don't freak out the woman...and you'll be much more likely to get a date.

6) Be Honest About Your Intentions at The Right Time

There is often a big difference between a woman's (or man's) initial preference and what they may end up finding attractive after knowing someone's personality (see HERE)...or will reassess as attractive at a later date (see HERE). Of course, women will initially say that they prefer clear and honest full disclosure up front. Just like, if I polled men, they would say that they hate being "misled" by body shapers, push-up bras, and makeup.If given the initial choice, everyone wants the "control" provided by full information about their dating partner, so they can be the one choosing and selecting the other. This is put succinctly by one of Dr. Kaufman's poll respondents:

"I would rather the guy be upfront and tell me what his intentions are in the beginning. At least if you know what his intentions are upfront you have the choice of whether or not if that's something you want to engage in. Verses the later when by the time you find out his true intentions you are already emotionally invested."

But, this initial choice may be misleading or superficial. Just like women learn to lessen men's "mistake" of making a superficial choice with their makeup and must also learn that appropriately timed disclosure of interest is necessary too. To further explain, after a man really "gets to know" a woman and has "fallen" for her, it doesn't matter when the makeup comes off. But, unless she is truly stunning, a woman often chooses to put her best foot forward initially with such accessories. Similarly, women will not respond favorably to the "direct approach" from a man until they are already attracted to him. In other words, if you're not a naturally handsome fellow, it is better to withhold your romantic interests initially, until the woman you desire gets to know your personality a bit better (see my advice HERE). Also, after they have "emotionally invested", they will be happy to have you, even if they didn't "choose" you initially (see HERE).

Therefore, only be direct and "hit on them" after a woman is attracted to you. If you do not have the looks (true for women too), then why rely on them? Shouldn't everyone have the opportunity for others to "get to know them" and appreciate them "as a person", without being judged "simply on their looks"?

So, keep your interests to yourself, until they really know you as a person and are attracted to the real you (or just wear makeup). Even better...postpone your full interest in THEM until you know them better as a whole person too. If you're still deciding on what you are looking for, then it isn't even "withholding" to not tell them. They're still helping you make your mind up too!

(Use this information here to help you evaluate them and decide whether they are the right girlfriend for you - SEE ARTICLE)

7) It's OK to Cut Your Losses After You Have Tried Your Best

It is important to keep a realistic sense of self. You are not going to be attractive to all women, at all times, under all situations. Some are going to say no, for a number of factors that you cannot influence. However, it is also important to not "give up" or "make excuses" before you've tried your best. AFTER you get rejected, it is perfectly acceptable to consider all of the reasons out of your control why she said "no" (as well as the reasons under your control). Before you've asked her out though, "cutting your losses" may be your loss. You may be missing the woman of your dreams, simply because the situation isn't "perfect".

If you're really worried though, or the situation isn't ideal, then you can always ask her out "indirectly" (see HERE). It is far better to ask indirectly, than not to ask at all!


Ultimately, while my advice may differ from Dr. Kaufman's, my conclusion does not. I too encourage men to never stop trying. Take risks, learn from rejection, and be courageous. I also encourage women to honor their need for comfort and safety - while simultaneously endeavoring to discern the difference between men's objective behaviors and the subjective interpretations they may project onto those behaviors. Meeting somewhere in the middle, with patience, understanding, and tolerance, is the only true "win win" for both women and men.

Primarily though, my goal in this article is to ensure that the voice and opinion of "nice guys" do not get squelched. Men's disempowerment is not the solution to this issue. That only does a disservice to both men and women. Good men with positive intentions should be encouraged in their assertiveness, their desires, and their pursuits (just like women).

So men, please use the above advice wisely. Respect the need for comfort, safety and trust of your female partners. Also, respect your own desires for love, sex, and companionship. Remember to foster attraction as well as trust. Remember too that you are as attractive and worthwhile as your indented date - giving her ample time to see it if it isn't obvious to her. Also, pay attention to feedback, but don't rely on it for permission to ask her out. Ultimately, it is your responsibility to be confident, assertive, try your best and just ask - only after can you "cut your losses" if it doesn't work out.

Go to for more dating and relationship advice (in helpful categories)!

Make sure you get the next article too! Click here to sign up to my Facebook page, Email, and RSS. I keep my friends informed :)
Finally, remember to share, like, tweet, and comment below.

Until next time...happy dating and relating!

Dr. Jeremy Nicholson
The Attraction Doctor

© 2011 by Jeremy S. Nicholson, M.A., M.S.W., Ph.D. All rights reserved.