Difficult question, as I'm generally really awkward and have tons of memories in that area, but nothing stands out to me, but there is one story where I know I made someone else feel really awkward. Needs a "little" intro for the story though, so that it makes sense.
I mostly grew up on the internet, didn't really have irl contacts, so I did not really have much of a mental association with gender and gender orientation. Basically, what eventually started bothering me was, that if I had the mental image of a person being female, I would automatically have more fun, be excited and have overall more motivation to invest time and attention into the friendship. Absolutely natural, but not for me at the time, it just annoyed me that one little information, that is only in my head, made such a big difference on my perception (since online you sometimes don't even know someones gender and sometimes only assume). It was only logical from my perspective, it felt unfair and annoying, I would want to have the same fun and excitement, the same emotions, no matter the gender. Didn't want to be manipulated by hormones.
So with the intro done, the story itself begins. Basically, there was a friend I had in a videogame that I started talking about this topic with. I've had many long conversations with him before about life / problems etc, so I didn't really think too much about it. I started sharing thoughts like "hypothetically, what if I were to fall in love with a person and that person turns out to be male" etc and was looking for genuine advice. I was telling him that I know what my hormones like and that it's clearly females, but since in my case, I primarily met people online, gender never really played a role on a mental/logical level and I strictly separated that from hormones, putting a much higher importance on what my conscious mind thinks, which in the context of my confusion and problem, really puzzled me, I just genuinely didn't know what to do with "gender" and the "what if's" of falling in love with someone rationally online.
While taking, I did feel that this topic made him feel really uneasy and awkward, but what I didn't know is, that it actually made him so uncomfortable, that he just litereally disappeared afterwards, never met him again. I did know him for over a year and had his email and did exchange emails a few times prior, but never heard or saw anything from him ever again. He was actually a good friend, I wonder if I litereally made him feel so awkward, that he decided to avoid me? Maybe he was thinking that I was trying to confess in a really awkward way, which obv wasn't the case, but who knows what went through his head really.
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