I’ve been trying to approach dating with more optimism. I want to take some initiative, be a little more playful, and stop defeating myself before a conversation even starts. At a party, out with friends, or doing something where there seems to be chemistry, I’d like to feel comfortable showing interest.
Instead, I often become extremely busy inside my own head.
I’m a sensitive person, and I care about making people uncomfortable. Talking with the women in my life and seeing accounts of harassment online has made that concern harder to set aside. I understand why an unfamiliar man’s attention might be unwelcome. The trouble is that I start assuming mine already is.
Then I watch every signal. Was that answer short because she wants me to leave? Did I say something awkward? Am I standing here too long? I’m trying to pay attention to her, but so much of my attention goes toward checking myself that I struggle to participate in the conversation.
The humor doesn’t come as easily when I’m reviewing each sentence before I say it. Neither does the part of my personality I actually want someone to meet.
Meanwhile, I see other guys who seem comfortable with all of this. They joke, flirt, and show interest without visibly getting tangled up. From the outside, they even seem able to recover from an awkward remark with some banter. I don’t know how much uncertainty they feel underneath that ease. I only know how effortless it looks.
I want to be respectful, and I also want to be able to let someone know I’m attracted to her. Right now, I have trouble doing both without turning an ordinary interaction into something I need to supervise.
If you used to approach dating this way, what helped you get more comfortable? Did experience make the signals easier to read, or did you learn to tolerate a little uncertainty while the conversation was still happening?
