Never really dated someone I didn't know

I usually have only ever dated people I knew well as a friend or an acquaintance. Not because I am demisexual or anything like that but without this my social anxiety basically causes my brain to lock up and the best pick up line I can muster is something like "you're pretty" like I am some nervous 13 year old....sigh.

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CassandraSissy · 26-30, T

I'm a little flirt on the outside, sweetie, but a little nerdy on the inside. The brazen hussy in me got me to say a couple of lines to my now fiancé but, if he didn't say anything back I would have just clammed up. Luckily for he said something or other to make me smile...and then we chatted a little later on and subsequent date came from that.

But I know what you mean. As trans I'd hazard a guess to say there's that bit more apprehension in case the person you like finds your fake in some way shape or form - 'fake girl' etc.

🤔

PicturesOfABetterTomorrow · 41-45, M

@CassandraSissy All of these recent posts are basically coming from being on my own again for the first time in 15 years and I am kind of lost at sea. And well dating is not something I was ever good at.

And can definitely understand why being trans can make things extra challenging. Fortunately there are guys out there present company included who don't care what is on a girl's birth certificate or what her girly bits look like.

CassandraSissy · 26-30, T

@PicturesOfABetterTomorrow Ah, ok. I get that. I think desperately looking for someone is the wrong way to go, just my own belief there...and, yes, I can see how making some sort of a connection - and friendship - with someone can make it easier. Makes a lot of sense.

I always try to look at what I can take from a situation like this. Not too sure about you. Me? I'd look at the freedom that it would give me to try new things/ideas/concepts that are things that we may have thought about but put off because they're out of our comfort zones or afraid of peer pressure (partner etc)....with only yourself to please...well...the world truly is your oyster.

☺️

PicturesOfABetterTomorrow · 41-45, M

@CassandraSissy I am not actually looking to jump into something in a huge rush. My previous relationship was "opened" a few years ago so I had met other people. The truth was it was really just me and my previous partner not being quite ready to admit the obvious that things were actually over between us in any romantic sense. And I thought with everything being official now I could really explore something new with someone new. But now it seems like they disappear for long periods without talking to me and then just pop back into my life like nothing ever happened and I feel sometimes I am just the safe plan B to come back to instead of someone they take seriously.

And I am also somewhat of two minds about my newfound freedom. Sure I would love to travel and do some things. But I am also 40 and I thought my days for playing the field were kind of behind me. So called "meaningful 24hr relationships" don't really have the same appeal anymore.

I guess I am just trying to figure out alot of stuff in my head. And I can't say the comments from the trolls are helping much either.