TessaReneeDear Tessa,
I don’t know if I should reach out, and that indecision has me stuck more than I expected. Part of me feels like it would be natural to check in, to see how she’s doing, to reopen a line of communication that doesn’t feel completely closed. Another part of me worries that reaching out would cross a boundary I don’t fully understand.
I don’t want to disrupt her peace if she’s moved on. I don’t want to show up late with words I should have said earlier. I keep asking myself whether this urge to reach out is about her or about me wanting relief from uncertainty.
There’s also the fear of rejection. If I reach out and don’t get a response, that silence becomes louder than before. Not reaching out lets me preserve the possibility that things are simply paused, not finished. I don’t know if that’s respectful patience or just avoidance.
I replay past interactions, looking for signs that reaching out would be welcomed. Did she leave the door open, or am I just hoping she did? I don’t want to read meaning into small details that don’t actually signal readiness or interest.
What makes this harder is that doing nothing doesn’t feel neutral anymore. It feels like a choice, even if it’s an unspoken one. Waiting hasn’t brought clarity. It’s just extended the uncertainty.
I don’t want to act impulsively, but I also don’t want to stay frozen. I want to do what’s considerate, honest, and grounded, not what’s driven by fear or nostalgia.
So how do you know when reaching out is appropriate versus when it’s time to let distance remain? And how do you make that choice without needing certainty first?
Signed:
A guy weighing the risk
Tessa’s Thoughts on the Subject
Reaching out becomes complicated when the motivation isn’t clear. It helps to ask whether the contact is meant to offer something grounded or simply soothe your own discomfort. The difference matters.
If reaching out is about accountability, clarity, or respectful communication, it can be appropriate. If it’s about easing anxiety, reopening access, or testing availability, it often creates more confusion than connection.
Distance can serve a purpose. Sometimes it creates space for reflection. Other times it signals an ending that hasn’t been verbally acknowledged. Reaching out doesn’t always clarify which one it is, but your intention going in can help guide the outcome.
You don’t need perfect certainty to act, but you do need self-awareness. Being honest about what you’re hoping for protects both you and her from misalignment.
Not reaching out is also a choice. If staying silent aligns more with respect, growth, or acceptance, that choice deserves to be honored too.
Tessa’s Straight-Up Perspective
Here’s the truth. Reaching out should come from clarity, not curiosity or fear. If you can reach out without expectation and with respect for whatever response comes back, it may be worth doing. If not, letting the distance stand may be the most honest answer. Sometimes the decision isn’t about getting a response. It’s about choosing the action you can stand behind.
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.
TessaRenee