Dear Tessa,
I keep going back and forth about whether I should text her, and it feels ridiculous that something so simple has turned into this much of a mental debate. I type the message, delete it, rewrite it, then tell myself to wait. I don’t want to come off as desperate or careless, but I also don’t want to seem uninterested. Somehow, doing nothing feels safer than doing the wrong thing.
Part of me thinks I should already know the answer. If I really wanted to text her, I would, right? But it’s not that simple. I care, I think. I just don’t always know what to say or how much to say. I worry about timing. I worry about interrupting her day. I worry about opening a conversation I’m not sure I’m ready to fully engage in.
I also don’t want to lead her on. That’s something I keep telling myself. If I text her, am I setting expectations I can’t meet? Am I starting something I don’t know how to follow through on? Sometimes it feels easier to stay quiet than to risk disappointing her later.
At the same time, I know silence can say things I don’t intend. I don’t want her to think I don’t care or that she doesn’t matter. That’s not true. I just don’t always know how to show up consistently without feeling like I’m committing to more than I understand yet.
I guess what I’m asking is whether texting her is about interest or intention. Is it better to reach out because I want to connect in the moment, or should I only text if I’m certain about where this is going? I don’t want to do the wrong thing, but doing nothing doesn’t feel right either.
So should I text her, or is waiting the more respectful choice here?
Signed:
A guy who doesn’t want to mess this up
Tessa’s Thoughts on the Subject
The hesitation you’re feeling isn’t really about the text. It’s about what the text represents. Reaching out feels simple, but it carries weight because it creates connection, and connection asks for some level of presence.
Texting her because you want to connect is not the same as promising her a future. Where things get complicated is when contact becomes inconsistent or unclear. If you reach out when it feels good and disappear when it feels inconvenient, the mixed signals create confusion on her end, even if your intention isn’t to hurt her.
Silence often feels neutral to the person choosing it, but it rarely feels neutral to the person receiving it. Waiting to text because you’re unsure is understandable. Waiting because you’re avoiding responsibility is different. The distinction matters.
You don’t need certainty to communicate. You do need honesty. If you want to reach out, do it because you want to connect, not because you’re trying to manage outcomes or control perception. And if you’re unsure about your capacity to engage, that’s something to be mindful of before opening the door.
Clarity doesn’t come from perfect timing. It comes from consistency and intention. Even small actions carry meaning when they’re repeated or withheld.
Tessa’s Straight-Up Perspective
Here’s the truth. Texting her isn’t the problem. Inconsistency is. If you want to reach out, do it with awareness of what contact communicates. If you’re not ready to show up with some level of steadiness, waiting may be kinder than sending a message you don’t intend to back up. Interest is easy to express. Intention is what makes it feel safe on the other side.
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.
