Dear Tessa,
I thought things were going well, which is why the shift caught me off guard. There wasn’t a clear problem. No argument. No obvious disconnect. From where I stood, things felt steady. Easy, even. So when the energy changed, I didn’t know how to place it.
We were talking regularly. Laughing. Making plans, or at least talking about them. Nothing felt strained. If anything, it felt comfortable. I assumed that comfort meant things were on track. I didn’t think I needed to push for more or ask deeper questions. I figured that if something needed attention, it would come up naturally.
Now I’m realizing that comfort for me may have felt like stagnation for her. What felt calm on my end might have felt unintentional on hers. I wasn’t checking in about where things were headed. I wasn’t clarifying my interest or naming my intentions. I just assumed the connection spoke for itself.
Looking back, I can see how that might have left her feeling unsure. I wasn’t pulling away, but I also wasn’t actively moving forward. I stayed present without being particularly intentional. I thought consistency was enough. I didn’t consider that consistency without direction can still feel uncertain.
What’s hard is that I didn’t feel like I was doing anything wrong. I wasn’t being careless or dismissive. I was just letting things be. But now I’m questioning whether letting things be was actually me avoiding the responsibility of clarity.
I don’t know if I misread the situation or if I underestimated how much intention matters, even when things feel good. I thought things were going well, but maybe they were only going well because she was carrying more of the emotional weight than I realized.
So how do you tell when “going well” is actually enough? And how do you recognize when comfort turns into complacency before it costs you the connection?
Signed:
A guy who thought steady was enough
Tessa’s Thoughts on the Subject
When someone says they thought things were going well, it often means things felt comfortable to them. Comfort isn’t a problem, but it’s not the same as progression. Many connections stall not because something went wrong, but because nothing moved forward.
Women often interpret “going well” differently. For them, it usually includes clarity, intention, and emotional direction. When those pieces are missing, comfort can start to feel like uncertainty. What feels easy to one person can feel unanchored to the other.
Consistency without intention can unintentionally place emotional labor on the other person. They’re left wondering where things are headed, whether their investment is matched, and if the connection has room to grow. That uncertainty doesn’t always show up as conflict. It often shows up as quiet withdrawal.
It’s understandable to assume that no problems mean everything is fine. But connection requires more than the absence of issues. It requires presence with purpose. Asking where things are going isn’t disruptive. It’s clarifying.
Recognizing this isn’t about self-criticism. It’s about awareness. Understanding that comfort and clarity aren’t interchangeable helps prevent future misalignment.
Tessa’s Straight-Up Perspective
Here’s the truth. Things can feel good and still not be going anywhere. Comfort without intention often leads to quiet endings. If you want to know whether something is truly going well, look at whether it’s growing, not just whether it’s calm. Connection needs direction, not just ease.
Disclaimer:
Dear Tessa: Letters From Men is written advice-style to explore emotional dynamics and common blind spots from a male perspective. It’s meant to offer clarity and reflection, not professional guidance or justification. You know your situation best.
