Dear Tessa,
I keep telling myself not to overthink this, but the more I try to stay relaxed about it, the more I feel caught in my head. I don’t want to analyze every interaction or read too much into small changes. I want things to feel easy and natural. But there’s a difference between staying grounded and ignoring something that doesn’t feel settled.
From my perspective, nothing is obviously wrong. We talk. We get along. There’s no conflict. So when I start feeling uncertain, I tell myself I’m creating problems that don’t exist. I remind myself that not everything needs to be defined, questioned, or dissected. Sometimes things are just… fine.
But if I’m honest, “fine” doesn’t feel as reassuring as I want it to. There are moments when I feel connected and present, and others where I feel unsure of where I stand. Instead of addressing that, I default to telling myself to chill out. To stop thinking so much. To let things unfold.
I worry that bringing this up would make me seem insecure or intense. I don’t want to turn something simple into something heavy. I don’t want to be the person who needs constant clarity or reassurance. So I keep my questions to myself and try to power through the uncertainty.
At the same time, I can feel that avoiding the conversation doesn’t actually make the feeling go away. It just pushes it into the background, where it keeps resurfacing. I don’t know if I’m being patient or just avoiding discomfort by pretending I don’t care as much as I do.
I’m trying not to overthink this, but I’m also starting to wonder if overthinking is just the word I use when something deserves attention and I don’t know how to give it that without disrupting the dynamic.
So how do you tell the difference between overthinking and intuition? And how do you address uncertainty without turning it into a bigger issue than it needs to be?
Signed:
A guy trying to keep it simple
Tessa’s Thoughts on the Subject
Overthinking is often a convenient label for discomfort you don’t know how to address yet. It’s easier to dismiss a feeling than to explore it, especially when things aren’t clearly wrong. But uncertainty that keeps returning is usually asking for acknowledgment, not suppression.
Trying to keep things easy can turn into emotional avoidance when it prevents honest communication. Calm doesn’t come from ignoring questions. It comes from clarity. When something feels unresolved, telling yourself not to think about it doesn’t actually make it settle.
It’s also worth noting that curiosity about a connection isn’t insecurity. Wanting to understand where you stand doesn’t make you demanding. It makes you present. Avoiding that curiosity to maintain a low-stakes dynamic often creates more internal tension over time.
The goal isn’t to interrogate every feeling. It’s to notice patterns. If the same questions keep surfacing, they’re not random. They’re information. Addressing them thoughtfully can actually reduce anxiety instead of increasing it.
You don’t have to dramatize uncertainty to acknowledge it. Simple honesty often creates more ease than silent restraint ever will.
Tessa’s Straight-Up Perspective
Here’s the truth. Overthinking isn’t the problem. Avoidance is. If something keeps pulling at your attention, it deserves a closer look. You don’t create clarity by telling yourself to stop caring. You create it by being honest about what you feel and allowing that honesty to guide your next step.
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.