I’ve been trying to approach dating with a little more optimism. I want to take initiative, be playful, and let someone know when I’m interested. At a party, out with friends, or doing something where there’s already a little chemistry, that sounds simple enough.
Then I start thinking about whether she wants me talking to her at all.
I’m a sensitive person, and I work hard not to make people uncomfortable. Talking with the women in my life and reading accounts of harassment online has made me more aware of what an unwanted approach can feel like. I understand why someone might be cautious.
But I’ve started carrying that awareness into conversations as an assumption that I’m already unwelcome. I catch myself expecting a woman to see me as a threat before she’s had a chance to know anything about me. I realize that’s my expectation; I can’t actually know what she thinks.
When I approach someone I don’t know, I monitor everything. Was that answer short? Am I standing here too long? Did that joke sound different out loud? I’m so busy checking whether I’m overstepping that I struggle to participate in the conversation happening in front of me.
The easy humor I’d like to bring disappears under all that supervision.
Meanwhile, the men I see doing well seem relaxed. They joke, flirt, and recover from an awkward moment without looking as if the whole interaction has collapsed. From the outside, it seems effortless. I don’t know how much uncertainty they’re carrying.
I want that ease. I also want to stay attentive to whether the other person is enjoying the exchange. Both matter to me, but lately I’m finding it hard to hold them together.
I’m willing to hear that someone isn’t interested. What I struggle with is entering every conversation braced for the possibility that saying hello was already a mistake.
For people who’ve worked through this, how did you learn to stay present enough to flirt while still noticing when it was time to step back?
