The Masculinist #4: How to Maintain and Establish Eye Contact

Welcome back to the Masculinist. Thanks to all of you for being a part of this effort to help build up the men of the church.  Please forward this to all Christian men you think would find it of value.

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Pastors are concerned about the many single women in their congregations who are not getting asked out, much less married.  For example, Matt Chandler complains that “Unfortunately, a lot of godly women get to a place where they are tired of the ‘weirdness’ of Christian dating and the apathy from Christian men to actually pursue them.”

Almost every men’s group I’ve been a part of has focused on this problem of “passivity” and apathy. The women are frustrated, and thus the pastors are frustrated on their behalf.  Pastor Kevin DeYoung hears it a lot. “As I speak at different venues across the country, one of the recurring questions I get comes from women, young women in particular. Their question usually goes something like this: ‘What is up with men?’ These aren’t angry women. Their question is more plaintive than petulant.”

As a reminder, every other month I’m focusing on practical, actionable things men can do to improve themselves as men. I want to build up, not just tear down. As part of this commitment, today and in the future, I’ll give some practical actions that men can take to help them meet, and ultimately marry, Christian women.

My Qualifications 

In the Masculinist, I’ll only presume to give practical tips in areas where I have the standing to dispense it and skin in the game.

One thing you won’t hear from me, for example, is advice on how to have a successful long-term marriage. I just got married in October.  I was previously married and it ended in divorce. Why in the world would anyone listen to what I have to say on the practicalities of marriage?  You’re better off tuning in to people with a long-term track record of success.  Some pastors who’ve written books on the topic have been married for decades.

On the other hand, there are a lot of things where I have way more personal experience and credibility than your average pastor. From what I’ve seen many pastors got married very young and dated at most only a handful of women ever. That’s a great thing actually – I wish I could say the same. But it also means those pastors have limited dating experience, period. They also never dated in the older age brackets in which most people become married today.  And many of the famous Evangelical leaders were married decades ago, meaning they have absolutely no experience at all in the harsh realities of today’s dating market. In the Catholic Church, most priests likely had little dating experience prior to taking vows, and the median age of priests these days is likewise fairly high.

I, sadly, have more dating experience than these men. So while I can’t tell you how to have a successful marriage, I can help you – or more realistically help you help the single men in your congregations and social circles – take the first step in that direction: actually meeting and asking out girls.

How Men Can Become More Confident and Successful in Asking Out Women

My first set of practical improvement tips help with building the social confidence necessary to meet women.  This is valuable on multiple levels.  On the one hand, women are attracted to confident men. On the other, you actually have to have enough confidence to approach a woman and start talking to her before you can even think about asking her out on a date.

Let’s be honest, this can be intimidating. Virtually all dudes have some level of anxiety and fear of rejection when approaching women. This is one of the riskiest things you can do from a self-worth perspective. Getting the door slammed in your face is hard enough when doing cold call sales. But at least then you can console yourself that it’s not personal. But with women, it’s very difficult to not see it as personal. After all, the product in question is you. Our brains are very good at spinning out disaster scenarios of being humiliated by rejection – especially if it’s someone in our social circle, such as a church, where we assume everyone will find out we got shot down in flames. No surprise, men too often exhibit the passivity and apathy that pastors are frustrated with. They aren’t confident enough to overcome their fear of rejection.

I can’t solve all your problems with this today, but I can share two techniques I personally used that helped me gain confidence with women.

The first will help you improve your eye contact. Good, strong eye contact is critical not just in meeting girls but in every relationship, so this one can really pay dividends.

I’m a very introverted guy who traditionally scored pretty high on the geek scale. I used to be a computer programmer, which should give you an idea. I was very bad at making eye contact. My social awkwardness was so bad at one point that my boss sent me off to charm school, aka executive coaching. Here is a snippet of the feedback I got from senior colleagues (collected anonymously).

There’s something about his head. He never really looks at you, and that puts people off. It creates unease….Aaron should lift up his face and look straight on at people. He’s got a nice face but it looks at you through the tops of his eyes with his face down. Maybe he’s shy or something. That’s off-putting.

That – and much more besides I can assure you – was not pleasant to receive, but super valuable. Everybody’s got a rap sheet. The only question is whether or not we know what’s on ours.

I improved my ability to make eye contact through a simple exercise I still do today. Everywhere I go I scan the people around me and try to make eye contact with them, whether that be walking down the street, riding the subway, or shopping in a store.  In NYC people tend to studiously avoid eye contact, but I’m still often able to pull this off.

So try that exercise. Get in the habit of trying to make eye contact with the people who come within range. And here’s the key: don’t avert your eyes when they notice and establish eye contact with you. Hold it 2-3 seconds before breaking eye contact. This isn’t easy – or at least it didn’t come naturally to me.

I never played football, but I’ve read that one reason players practice hitting a blocking sled is to train themselves to make full force contact with opposing players without pulling back or flinching, which is our instinctual reaction. I see this eye contract drill as sort of like practice hitting a blocking sled. The idea is to make it second nature to be able to establish and maintain strong eye contact, by repeatedly doing it in a low risk, “practice” setting.

The second drill is to take the next step and make a habit of striking up conversations with people.  I’m less obsessive on this than on eye contact, but I’m always looking for ways to initiate brief remarks to someone. There are plenty of settings where this is very appropriate to do, such as with a clerk who is ringing you up in the story. Or just say something to the person next to you in line. Or compliment someone on the train who is wearing a particularly cool piece of clothing.  Or make a comment to someone about his dog.

Don’t try to force someone into a long conversation. Just a couple of sentences will do. Talk to everybody – male and female, young and old (though never talk to minors unless their parents are present).  Don’t worry about impressing them or even thinking about asking any of them out.  The point is simply to build the social confidence to initiate a conversation with a stranger or someone you don’t know well.  This can be awkward, but if you can’t even exchange a few pleasantries with a store clerk, how you ever going to ask a woman out?

These are just two simple and easy ways for shy or timid guys to start building social confidence – something that will pay dividends far beyond the dating world. Once you get to the point where you’re able to make strong, unapologetic eye contact, walk up to a woman, and initiate a conversation, you’ve taken the first step.

How a Woman Can Show a Man She Is Interested in Him

The Masculinist is for men. But many of you are pastors or have daughters and so may be in a position where you’re called on to give counsel to women on this same topic. So I’ll give you one simple technique women can use to show a man that she’s interested or at least would welcome him talking with her.

Again, it’s intimidating for men to even approach and talk to women, much less to ask them out. They are much more likely to do so if the woman in question has somehow let it be known that this would be welcome. This is the ballet dance of dating. Men are expected to initiate, but generally only after the woman signals that she welcomes it. Realistically most men don’t do too many “cold calls” on women. (For reasons I’ll explore in the future, the ones who do often aren’t great marriage prospects). They wait for some indication of interest first. This is especially true today when men are very sensitive to not wanting to be perceived as making an unwanted advance on a woman.

There are more college-educated single women in New York than there are college-educated men.  The sex ratio in the church is even more skewed, especially when you get into the default age range for someone who would date me. So I start out with the numbers very much in my favor. I’m also personally a pretty high-quality product: solid-looking, have a reasonably high-status job, a decent game with women, etc.

Yet in my experience, few women in the Christian settings I’ve been in have given me any indications of interest.  This contrasts with women in secular society, who often do give them off.  I talked with a Christian friend of mine in New York about this, and he had the same experience. Despite the poor dating ratios in church, Christian women seem to give off fewer indicators of interest to men than non-Christian women do. They are much more likely to be sending out signals that they don’t want to be approached, whether they realize it or not. This may not be universal. But this has been my experience.

So for Christian women who are single and frustrated, one simple way to increase the number of men who show interest in them is to start giving off more explicit indicators of interest themselves.

There’s one very easy way to do this: establish eye contact with the guy in question, then smile. Repeat once if necessary. It’s really that simple.  This doesn’t guarantee that he will come to talk to her. But it will significantly increase the odds.

And guys, when she smiles at you after you make eye contact with her, you know what to do.

Setting People Up on Dates

While the single Christian women I see in New York largely seem indifferent to their status (based on the lack of interest signals they give off), Christian leaders and middle-aged married men here are very concerned about it.  I know this because virtually every one of them I’ve met wanted to set me up on a date with someone, often bringing it up the first time I really talked to him.

This is a great thing. It’s very good that so many married people and church leaders are trying to help others find great matches. But I always declined to be set up directly with someone.  I have multiple reasons for this, but one of them is that for anyone I dated, I wanted to be the one who initiated and made the ask.

As I said, a strong, confident man is a high quality, attractive product. A weak, timid man is not.  Walking up to a woman, initiating a conversation with her, and ultimately asking her on a date demonstrates strength and confidence.

By contrast, being explicitly set up on a date makes the guy look weak. It’s not a formally weak position, as it would be if the girl had asked him out, but weakness will be conveyed nevertheless. For men like me who aspire to lead in their relationship, you want to establish that as the frame right out of the gate.  That means you want to clearly be the initiator in asking the woman out.

That doesn’t mean that pastors or others can’t help bring people together. The person who introduced my wife and me is a case in point.  In church one morning, she introduced us with the suggestion that we might have professional areas of overlap. Then she walked away. She may have intended it as a legitimate professional introduction. The woman in question is an uber-connector who is always bringing people together. But when one woman wants to introduce me to another, a single one in my age range, I always assume an ulterior motive. In any event, she left it up to me to take this from the professional level to the personal level. I did, and the rest is history.

There are plenty of ways to arrange for people you want to set up to meet each other in a setting where nature can take its course. You can even give it a shove by telling the guy offline who the woman is so that he’s aware of what’s going on and is prompted – kicked in the butt if necessary – to take action if he is interested in her.

In Summary


  • Confidence is attractive to women in its own right, and necessary to even get to square one.

For Men:

  • Make a habit of establishing and holding eye contact with people you are around.
  • Make a habit of initiating brief conversations with people you come in contact with.

For Women:

  • If there is a man she wants to come to talk to her, she should make eye contact with him and smile. Repeat once if necessary.

For Pastors and Married Couples:

  • Arrange introductions or social encounters to bring prospective couples together, but avoid directly setting up on dates if possible.  Clue the guy into what is going on if you think he needs to be prodded.

In the Culture

Our culture today, including too often church culture, disparages masculinity. In fact, hostility to masculinity is an almost uniform elite stance. When I have space, I will point this out by citing examples in the culture.

This month it’s a Huffington Post article featuring the work of photographer Jo Imperio (note the androgynous name and her troubled relationship with her father). The headline is “Sensual Photos Shatter The Idea That Strong Men Can’t Be Vulnerable.” It’s a gallery of photos of men in traditionally female poses. Here’s a sample, if you can stomach it:

A very gentle man


If you’re not familiar with the Institute for Family Studies (IFS) at the University of Virginia, you should check it out. They’ve got a weekly email blast you can sign up for with all sorts of interesting tidbits of academic research on families.

IFS shared a personal story about the “overlooked fatherless,” children conceived through sperm donation.

IFS also noted that family instability has negative effects on daughters, not just sons.

The New York Times ran an op-ed talking about the problems of men and possible solutions.  This bit caught my eye:

But in the long term, Isabel V. Sawhill and Richard V. Reeves, senior fellows at the Brookings Institution, argue that men must resign themselves to working in “pink-collar jobs” — those known by the acronym HEAL, for health, education, administration, and literacy.

Economically, “women have adjusted better than men,” Ms. Sawhill said. “They’re the ones who are winning.” Women dominate the (often lower-paying) service jobs that are the backbone of the new economy. Men make up just 20 percent of elementary and middle-school teachers, 9 percent of nurses, 16 percent of personal aides, and 6 percent of personal assistants, Ms. Sawhill and Mr. Reeves noted.

Succeeding in the new economy and culture may well require rethinking conventional ideas about masculinity. Mr. Cherlin bemoans men’s “continued reluctance to take jobs they think are beneath the dignity of real men.”

The Art of Manliness contrasts Achilles vs. Hector as archetypes of manhood.


“What I think, fundamentally, is that you can’t do anything about major societal changes. It may be regrettable that the family unit is disappearing. You could argue that it increases human suffering. But regrettable or not, there’s nothing we can do. That’s the difference between me and a reactionary. I don’t have any interest in turning back the clock because I don’t believe it can be done. You can only observe and describe. I’ve always liked Balzac’s very insulting statement that the only purpose of the novel is to show the disasters produced by the changing of values. He’s exaggerating in an amusing way. But that’s what I do: I show the disasters produced by the liberalization of values.” – The Art of Fiction (Paris Review interview with Michel Houellebecq)

“The mere will to live was clearly no match for the pains and aggravations that punctuate the life of the average Western man. I was incapable of living for myself, and who else did I have to live for? Humanity didn’t interest me—it disgusted me, actually. I didn’t think of human beings as my brothers, especially not when I looked at some particular subset of human beings, such as the French, or my former colleagues. And yet, in an unpleasant way, I couldn’t help seeing that these human beings were just like me, and it was this very resemblance that made me avoid them. I should have found a woman to marry. That was the classic, time-honored solution. A woman is human, obviously, but she represents a slightly different kind of humanity. She gives life a certain perfume of exoticism.” – Michel Houellebecq, Submission

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