I’m Not Afraid to Approach, But Things Always Stall After a Few Dates. What Am I Doing Wrong?

By Courtney Schand | Relationship Coach

You’ve done the work. You can approach a woman and even ask her out. You show up, you’re a gentleman, you say the right things. And then, after two or three dates, something seems to quietly die. She says she’s “not feeling it”. Or the connection fades. Or she tells you she thinks you’re looking for “different things”.

And you’re left genuinely confused, because you can’t identify specifically what happened or what you could do differently next time. You weren’t rude. You weren’t pushy. You were everything you’ve been told a “good man” is supposed to be.

But here’s the thing- you probably weren’t doing anything wrong. There is just something you weren’t doing at all. And that absence is likely what she was responding to.

The Real Reason Things Stall Out

The most common pattern I see in men who stall out after a few dates is this: they’re doing everything correctly and simultaneously removing themselves from what we call “the relational field”.

What that means in practice is that you have a longstanding habit of dissociating from your body in interpersonal situations. You think you’re being objective, present, and attentive (which usually makes you great in an analytical career like engineering, law, medicine, software, etc). Because in a cognitive sense, you are being those things. But the relationship requires something you can only access viscerally. So when you’re not willing or able to engage at that level, you’re missing the cues that would help you navigate the connection. And she’s feeling something she probably can’t quite name- that she can’t actually reach you, even though you’re right there.

The result is that your actions feel mechanical when she’s looking for an organic experience. Essentially, you’re executing the behaviors of connection while being absent from the feeling of it. And she senses that immediately, even if she couldn’t explain it if you asked her to.

This isn’t a character flaw. It’s simply a habit; a well-developed strategy of staying in your head during moments of intensity that worked in other contexts and is actively working against you here.

Why Waiting for Signs It’s Safe Is Backfiring

When you’re trying to be objective, you’re waiting for clear signals from her that make it safe enough for you to bring more of yourself into the exchange. Your thoughts, your opinions, your desires. That feels responsible and respectful. But what it’s actually doing is putting the entire weight of the connection on her. Which means she may be trying to engage warmly, but she’s confused about why she can’t quite connect with you. She can feel that you want to connect. She just can’t energetically “find” you in the space.

So she keeps trying. She stays warm. She engages. But she can’t fully relax into the dynamic because there’s nothing stable on the other side for her to relax into. And by the time you feel comfortable enough to step forward, she’s already concluded that this person isn’t available for what I’m looking for.

The “I’m just not feeling it” is almost never about what you did. It’s about how she felt around you. And those are two very different problems with very different solutions, which is why doing more of the right things isn’t translating the way you’d expected.

What She’s Actually Looking For and Not Finding

Women are instinctively visceral in how they read connection. This means she’s not primarily evaluating what you say. She’s reading how she feels in your presence, whether the space between you feels alive or stifled, open or contracted, like something’s being shared or something’s being performed.

When you’re present, and she can actually feel you in the exchange, something shifts for her. What you share starts to land. It has impact. She can sense your genuine interest and your genuine curiosity about her, and she can let herself be curious in return. The connection starts to feel mutual rather than one-directional.

She also starts picking up on whether there’s genuine compatibility, which is actually a good thing. Because the men in this situation tend to be genuinely great potential partners, when she’s finally getting that sense of emotional safety and real presence from him, she’s often pleasantly surprised by what he’s actually looking to create. And if it’s aligned with what she wants, there’s nothing stopping her from continuing to move toward him.

The problem was never that you weren’t what she was looking for. It was that she couldn’t see enough of you to know.

What Actually Has to Change

The shift isn’t behavioral. You can’t think your way into presence. And you can’t perform your way into it either, which is why “be more confident” or “flirt more” or “create more tension” tends to feel hollow when you try it. If you could just do those things, you would. The reason they don’t feel genuine is that confidence, flirtation, and natural tension are what Andrew refers to as “emergent” qualities. Meaning they show up when something else is happening, not as behaviors you execute on top of dissociation.

What you actually need is to start including yourself in the interpersonal moment. To be present with your own experience of what’s happening rather than observing it from a safe, cognitive distance. That means being willing to feel what’s there, the charge, the uncertainty, the pull, and stay “in the room” with it rather than retreating into your head.

This is genuinely uncomfortable at first because those sensations are exactly what you’ve learned to dissociate from. That’s why having guidance and a regulated space to practice helps significantly. It’s hard to expand into something new when you’re also managing the anxiety of doing it alone. But when you do start practicing staying present, something shifts in how people engage with you. You start getting different feedback. And that feedback becomes its own motivation to keep going.

The work we do in Grounded is built specifically around helping men develop the perceptive awareness that keeps them present and included in the relational field, rather than managing it from the outside. I have a full post on how that works if you want to go deeper into the mechanics. But the most important thing to understand right now is that the shift you need isn’t about doing more. It’s about being more present while you do what you’re already doing.

What It Looks Like When It Starts Working

The pattern I work on with men in this situation is specific. I help them step forward energetically until I can actually feel them in the space. They are often holding themselves further back than they realize, and this isn’t only in relationships.

What they start to notice is that the moments they’d been stalling out in were exactly the moments they’d been falling back. Waiting. As a result of having a felt-sense of what leaning in feels like, those are the moments that now become the ones where they step forward instead. And the whole exchange starts to feel different, more natural, more mutual, more alive.

They also start to be able to actually discern goodness of fit. Because when you’re so focused on showing up correctly, you’re not paying attention to whether you actually like her or whether this is the kind of connection you want to build. When you’re present, you can vet. You can notice what you’re actually experiencing and let that inform whether you want to keep moving forward.

Most of these men had already mastered being a gentleman. That was never the issue. The difference, when the shift happens, is that they’re finally participating. And that changes everything about how she experiences them.

Something Small to Try on Your Next Date

You don’t need to overhaul everything at once. Here’s one concrete place to start.

On your next date, notice your posture. Do you instinctively lean back, create physical distance, and keep yourself slightly removed from the space? Or do you lean forward and engage?

Try adjusting your posture toward engagement and notice what shifts in your perception. Not as a technique to impress her, but as a way of prompting your body to be present rather than held back. Posture can be a doorway into the body, not just something other people can see. When you orient physically toward the moment, your internal experience of it often follows.

It’s a small thing. But it’s a real thing. And noticing what changes when you do it is the beginning of understanding what presence actually feels like from the inside, which is the whole game.

Ready to Go Deeper?

If you want to start building the internal anchor that keeps you present in the moments that matter most, Break the Ice is a great starting point. It’s a 5-module training designed to help you connect with your own agency and presence rather than scanning for external signals of approval. You can find it at courtneyschand.com/break-the-ice.

And if you’re ready to do the deeper embodiment work, developing your perception and skills that make presence sustainable rather than effortful, Grounded: The Embodiment Experience For Men is where that happens.

Courtney Schand is a certified relationship coach who works with men to develop authentic masculine presence, emotional intelligence, and deeper relationship skills. She co-hosts the For the Love of Men Podcast and she and her partner, Andrew, offer coaching through 1:1, group, and self-paced resources.