Dear Tessa,
I think I missed my chance, and I can’t tell if that realization is accurate or just something I’m telling myself now that things feel distant. At the time, I didn’t think I was doing anything wrong. I was taking things slow. I was figuring myself out. I assumed that if something mattered, it would still be there when I was ready.
Looking back, I can see moments where I hesitated instead of acting. Times when I should have been clearer, more present, more intentional. I told myself there was no rush, that pressure ruins things, that waiting was the responsible choice. But I didn’t consider how waiting might feel on the other side.
I didn’t think silence would read as disinterest. I didn’t think inconsistency would create doubt. I assumed the connection was understood, that it didn’t need to be reinforced. Now I’m realizing that what felt like patience to me may have felt like uncertainty or neglect to her.
What’s hard is that I didn’t lose interest. I just didn’t know how to step forward without feeling like I was committing to more than I could promise at the time. I wanted to keep the door open without walking fully through it. I didn’t realize that doors don’t stay open forever without someone standing there.
Now I’m left wondering whether it’s too late to say something. Whether reaching out now would feel genuine or just reactive. I don’t want to disrupt her peace or reopen something she’s already moved on from. But I also don’t want to live with the regret of never saying what I should have said when it mattered.
I don’t know if I missed my chance, or if I just failed to recognize it while it was there. I’m trying to figure out whether this is something I should accept or something I should finally speak up about.
So how do you know when a chance has passed? And how do you decide whether reaching out now is accountability or just self-soothing?
Signed:
A guy who waited too long
Tessa’s Thoughts on the Subject
Missing a chance often isn’t about one moment. It’s about a pattern of hesitation that slowly creates distance. Opportunities for connection usually don’t disappear suddenly. They fade as clarity and consistency fail to show up.
What you’re feeling now isn’t uncommon. Many people don’t recognize the weight of their inaction until the dynamic shifts. When someone stops reaching, stops waiting, or stops making space, it can feel abrupt, even if the process was gradual.
Reaching out after distance isn’t automatically wrong, but intention matters. Are you reaching out to take responsibility for what you didn’t offer before, or are you reaching out because you’re uncomfortable with the loss of access? That distinction is important, both for you and for her.
It’s also worth recognizing that regret doesn’t always mean a door should reopen. Sometimes it means a lesson has landed. Accountability doesn’t require a response. It requires honesty with yourself about what you avoided and why.
If you do choose to reach out, clarity is kinder than nostalgia. Naming what you didn’t do matters more than revisiting what you felt. And accepting her response, whatever it is, is part of that accountability.
Tessa’s Straight-Up Perspective
Here’s the truth. Chances aren’t missed because someone wasn’t ready. They’re missed because readiness never turned into action. You can acknowledge that without trying to reclaim what has already moved on. Growth doesn’t always mean reopening the door. Sometimes it means learning how to show up differently next time, before silence does the choosing for you.
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.
