Dear Tessa,
I don’t know when to let go, and I’m starting to realize that not knowing has kept me stuck longer than I want to admit. I keep telling myself that holding on is the mature thing to do. That walking away too soon means I didn’t try hard enough. That if something mattered, it deserves patience and effort.
The problem is, I can’t tell if what I’m holding onto is still real or just familiar. There’s history here. There’s connection. There are moments that remind me why I stayed in the first place. But there’s also distance, hesitation, and a growing sense that I’m putting energy into something that isn’t moving forward.
I keep asking myself if letting go means giving up. If it means I failed to show up the right way or didn’t do enough at the right time. Part of me worries that if I let go now, I’ll regret it later. That I’ll realize too late that I should have tried harder or waited longer.
At the same time, holding on doesn’t feel good either. It feels heavy. It feels like I’m suspended in a space that doesn’t fully include me anymore. I don’t feel fully chosen, but I’m also not fully released. And that in-between space is exhausting.
I tell myself that clarity will come eventually, that something will shift and make the decision obvious. But nothing has shifted. I’m still here, still hoping something will change, still unsure whether staying is loyalty or avoidance.
I don’t want to walk away out of fear. I don’t want to stay out of comfort. I just want to know when holding on stops being hopeful and starts being harmful.
So how do you know when it’s time to let go? And how do you do it without turning it into regret or self-blame?
Signed:
A guy afraid of choosing wrong
Tessa’s Thoughts on the Subject
Letting go is rarely about one final moment. It’s usually about recognizing a pattern that hasn’t changed despite time, effort, or intention. When you’re constantly waiting for clarity that never arrives, that’s information in itself.
Many people stay longer than they should because letting go feels like failure. But release isn’t a judgment on what once mattered. It’s a response to what no longer aligns. Holding on doesn’t become noble just because it’s familiar or emotionally charged.
It’s also important to notice how much of your energy is spent managing uncertainty. When a connection is still alive and mutual, effort feels purposeful. When it’s fading, effort feels like maintenance without momentum. That difference matters.
Letting go doesn’t require certainty. It requires honesty. If staying means continuously overriding your instincts, minimizing your needs, or accepting ambiguity as the norm, it may be time to reassess what you’re protecting.
You don’t have to demonize the past to move forward. You just have to stop waiting for something to become what it hasn’t shown itself capable of being.
Tessa’s Straight-Up Perspective
Here’s the truth. You don’t let go because you stopped caring. You let go because holding on started costing you clarity and peace. If staying requires you to live in limbo, that’s not loyalty. That’s avoidance. Letting go isn’t choosing wrong. It’s choosing to stop waiting for certainty that isn’t coming.
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.
