Dating and Waiting—What Every Dating Woman Needs to Know About Men (part 1)

These days, I’m pondering some truths that might help younger generations. Last month, my daughter got married. We are currently doing research with Gen Z and younger millennials. And I spent this past weekend speaking on the Harvard campus and talking to dozens of students and recent alums who are asking questions about the future.

Basically, I find myself spending a lot of time around those who are dating, engaged, and newly married. There is plenty of intrigue and excitement. But there are also whispered questions, anxious looks, and the occasional heavy sigh that says, “This so much harder than I expected.”

The Harvard trip pulled me back to one of the most important lessons I had to learn when Jeff and I had become great friends in grad school, and I was wondering if he was ever going to define the relationship—at least in the way I wanted him to!

Here’s the lesson—one that will eventually impact a lot of things in marriage: Since a man will often handle things differently (or at a different pace) than a woman, she will have to grapple with whether and how to trust him in that.

This trust issue relates directly to several other truths about men that are backed by more than twenty years of research and explored in greater length in For Women Only and other books. For example, a man can look confident on the outside, while carrying a surprising amount of self-doubt on the inside. And he probably needs to think something through internally before he feels comfortable talking about it. And (assuming he is responsible) he knows how much his girlfriend is getting attached—and wants to protect her heart rather than play with it. In all of this, a man is probably subconsciously watching and hoping to see that the woman in his life will choose to trust him. This conveys a sense of respect and belief in him that often matters far more than she probably knows.  

I’ve written about these truths for established relationships many times before. But watching the younger generation has reminded me just how crucial this lesson is during the dating phase—when patterns are being formed that can last a lifetime.

So in this part 1 of a two-part series for couples who are dating or engaged, I’ll tackle how important trust is to a man. I’ll follow up in part 2 with a key truth young men need to know about women.

The classic conundrum

I remember talking with a 28-year-old woman who had been dating a genuinely good man for a bit more than a year. He was kind. Steady. Responsible. The kind of guy a parent hopes their daughter brings home someday.

She was frustrated.

“He knows that I’m not interested in dating just to date,” she told me. “I’ve been clear that I want to move toward marriage. But all he says is that he’s ‘thinking about things.’ Nothing more concrete. How do I get him to get a move on? I’m not getting any younger!”

I nodded. I understood the anxiety. And then I said something she did not love hearing.

“I think you actually have three choices.”

She leaned in.

“One,” I said, “you can try to essentially force him to move forward—an ultimatum, or something close to it.”

She grimaced. She had been thinking about doing just that.

“Two, you can decide that he’s not responding in the way you need, break things off, and move on.”

She nodded again. Painful, but clear.

“Or three,” I said gently, “you can trust that he really is thinking about it—and stop trying to make something happen.”

She groaned. “Ugh. That is REALLY hard.”

This is where the deeper lessons come in—ones that are good to grapple with before marriage. In this space we don’t have room for all the lessons but here are three important ones:

1. Men’s confidence is often thinner than it looks

One of the most surprising findings from the nationally representative surveys of men for For Women Only was that many men walk around with a persistent, quiet question in the back of their minds: “Do I measure up?”

They may look confident. They may sound decisive. But underneath, many are deeply aware of their shortcomings and intensely sensitive to feeling like they’re failing—especially in areas like providing, leading, or making big life decisions.

So when a woman asks him, “What’s taking so long?” it may land not as a neutral question—but as confirmation of his deepest fear: I’m not enough.

This doesn’t mean that her desires are wrong, or that she should set them aside. But it does mean the way those desires are expressed matters far more than women often realize.

Dating is the first arena where a man begins to sense: Is this someone who believes in me… or someone who will always feel ahead of me, pulling me along? The ultimate goal in marriage is oneness, which requires mutual respect. Many of us simply don’t realize how much we signal the opposite: that we want to be the one in charge, and he’d better shape up or keep up. That is not a recipe for a happy marriage.

And that brings us to the second lesson.

2. Dating is a bootcamp for examining trust and practicing respect

Now that we know how important respect is for a guy, many women assume we learn that in marriage—and we will, of course. But dating is where you examine the question: Is this even someone I can respect and trust? If the answer is yes, dating is where you do the hard work of putting that into practice. Dating is where we learn not just how willing he is to become the person we need, but how ready we are to become the person he needs.

Respect doesn’t mean silence. It doesn’t mean suppressing your hopes. And it certainly doesn’t mean waiting forever. But it does mean learning to speak in ways that communicate trust rather than pressure, belief rather than disappointment.

In the story above, the 28-year-old woman wasn’t wrong to want clarity. But she faced a deeper question: Could she respect a man who was methodical and slow about decisions? If she married him, that trait wouldn’t disappear. It would show up again and again in decisions about money, parenting, career moves, and everything else.

Dating is where you begin to see things like: Does he follow through? Does he take responsibility seriously? And does his “thinking about it” eventually turn into action?

Just as important, dating is the time to ask: Can I trust him without controlling him? Can I respect a pace that isn’t mine?

This leads to the third and maybe hardest lesson.

3. Trust now shapes the marriage you’ll have later

I said to that young woman, “If you marry this man, you’re going to have a lifetime of needing to trust him.”

A lifetime.

The alternative is also a lifetime—but one where you carry the weight of directing, managing, and pushing everything forward. I have yet to meet a marriage where that dynamic feels good to either person.

Now, of course, trusting someone doesn’t mean ignoring red flags. It doesn’t mean silencing your own needs. And if trust has been broken, it shouldn’t be given back blindly—it has to be earned through, as one of my friends puts it, “time and believable behavior.”

But assuming red flags and broken trust are not in play, if you watch him closely and believe this man is someone so trustworthy that you want to marry him, then what probably has to happen is the choice to trust. This is part of not just choosing the right person, but becoming the right person.

If you are interested in having Shaunti bring research-based strategies, practical wisdom and biblical principles to your next event, please contact Nicole Owens at [email protected].

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