5 Tricks to Making a Relationship Work With a Man

He's charming on the first date and tells you all about his golf game. Then you ask how he's feeling about the two of you, and the conversation goes flat.

Sound familiar? You're not imagining it, and you're not doing anything wrong… on purpose.

As a dating coach for over 20 years, I regularly hear this from women dating again after 50: "He's a closed book. How do I get him to open up?" In today's world of texting and apps, it can feel even harder to know what a man is really thinking.

Here's what makes a man feel safe enough to share, and what shuts him down. Much of it comes from Alison Armstrong, who has spent 35 years studying men. I took her course years ago and still credit it for lessons that helped my marriage.

The Main Reason Men Have a Hard Time Opening Up

The main reason is self-protection. According to Alison, near the top of a man's instincts is hiding anything that could be used against him. Those defense mechanisms often form at a young age and harden over a lifetime.

That's why a man will tell a stranger on a plane what he's never told his wife.

So the real question becomes: how do you turn into a romantic partner he doesn't need to guard against?

The First Step: Become a Safe Space

Alison uses a phrase the men she studies use themselves: safe to talk to. A woman who's safe to talk to hears what he shares and never turns it into ammunition. Safety is the key ingredient in any intimate relationship.

Two everyday habits wreck that feeling fast:
✅ Repeating something he confided to your girlfriends, even proudly.
✅ Picking apart plans he thought through carefully.

The first step toward emotional intimacy is making sure he never regrets telling you something. That small thing goes a long way.

I learned this the hard way. My husband stopped talking to me years ago, and a big part of it was my interrupting. Once I became a good listener, he started talking again.

Ask What He Thinks, Not How He Feels

This is the tip I've used ever since Alison's course: ask a man what he thinks.

Most women can name their own feelings in a heartbeat. For many men, "How do you feel?" sends them searching somewhere remote inside, while what he thinks is right there.

Try: "What did you think about how tonight went?" From his answer, you can gently guess at the emotion underneath and offer him words for it. That's a great way to build emotional connection without pushing.

One condition from Alison: honor what he says. Laugh at it or argue with it, and he may stop sharing his thinking with you.

Active Listening Without the Interrogation

Here's the burning question I put to Alison: if I teach women to ask questions in early dating, how else will they learn about a man?

Her answer surprised me. When she asked a room of men how many questions make an interrogation, they told her 1.

Her alternative is what she calls a playground. Tell him you'd love to hear more about a few things from his profile, plus anything else he'd like to share.

I still like essay-style questions, especially when you share your own answers first. Either way, skip the rapid-fire checklist and practice active listening, taking in what he says without planning your reply. If you want more ideas, here's how I help women get a quiet man talking.

Science backs this up. A 2017 study in Personality and Social Psychology Bulletin found that when listeners were empathic and nonjudgmental, the people speaking to them felt less social anxiety and became less defensive.

Knowing what to ask, and what to leave alone (for now), is a skill you can learn. The trick is tying your questions to what actually matters to you in a partner. That's why I built my early-dating approach around getting real answers without turning dates into job interviews.

In my free webinar, 3 Secrets to Finding and Maintaining Healthy Love, I walk you through the Head, Heart, and Hoo-ha framework created by my mentor Lauren Handel Zander, and my 3-date strategy.

Body Language and Nonverbal Cues That Help a Man Feel Safe

Before he says a word, he's reading you. Crossed arms, a phone on the table, or intense eye contact can all feel like pressure.

Try these instead:
✅ Sit side by side at a bar, or take a walk together.
✅ Keep your gaze warm and relaxed rather than locked on.
✅ Let pauses breathe instead of filling them.

These nonverbal cues help a man feel relaxed enough to keep going. And if your date talks too much, that's usually nerves too.

Watch the Episode: He Won't Open Up Until You Stop Doing This One Thing

There's much more where this came from. My full conversation with Alison is packed with such deep insight into how men think.

She shared one listening switch that changes what you notice about a man on a date. It connects to why a man sees one woman as special and another as merely attractive.

It's a mindset shift that changes how you walk into your next first date. Hear her explain it in the episode here:

Emotional Health and Small Steps Build Trust

Alison teaches men that only about 5% of a woman's happiness is within their control. The rest is ours.

In her view, a woman who tends to her own emotions and emotional health shows a man she can be made happy, and men are drawn to that.

Opening up takes time, and every man does it in his own way. Take small steps: receive the first time he shares with care, honor his moments of vulnerability, and keep his confidences. That's how you build trust, the bedrock of any good relationship, and how you connect on a deeper level. Those are the building blocks of a strong relationship.

Next time he goes quiet, resist the urge to dig. Let him come to you.

Love,

Frequently Asked Questions about How to Get a Man to Open Up

Why do men struggle to share feelings in romantic relationships?

Many men learned early that what they reveal can be used against them. Asking what he thinks usually gets you further than asking how he feels.

What's the best way to get a man to open up on a first date?

Keep the setting low pressure, like a walk or a quiet spot where you can sit side by side. Invite him to talk about things you already know interest him, and share your own stories too.

What if a potential partner's unwillingness to talk doesn't change?

If you've been safe, patient, and curious and he still stays shut down, that's useful information. In early dating, decide whether he's emotionally available enough for what you want.

How long does it take for a man to feel comfortable opening up?

There's no set timeline. Consistency matters so keep showing up the same warm way for at least 3 dates if everything else is good.

Is trust really the most vital ingredient in a healthy relationship?

Trust is what makes everything else possible. Without it, no one risks being vulnerable, and closeness can't grow.