So, I thought I'd post this here, see what people think about my "situation," and then let the thread naturally evolve for anyone else if they wanted. Basically, I'd like to talk about dating with respect to being trans, specifically looking for potential longer-/ long-term relationships, initiating, etc.
Warning: the first paragraph recounts my break up last year and is kinda depressing so, you might want to skip it if you'll feel uncomfortable reading.

I've had three girlfriends over the past 16 years, and have been on one date. Ever. To clarify, none of my girlfriends lived near me; the first one almost doesn't count because we were kids, and I broke up with her because she couldn't use grammar, haha. The second one somehow 180'ed her sexuality (thought she wanted a trans boy, actually wanted a trans girl - we were teenagers) so, she broke up with me. Fair enough, sometimes, people are just lesbians and don't know it, haha. My most recent relationship was not until 11 years later (last year). She was my first love; I'll always love her, there's no way around it. She's kind, and smart, and talented, and beautiful. She made me laugh, and no one ever makes me laugh. I had hoped to marry her; I'd even picked out a promise ring.

Long story short, she fell into a depressive spiral, mostly over her fear of coming out (she's also transgender). I would have done anything to fix things for her but I found out the hard way that it's impossible to give happiness to another person. In the end, even when she said that she was too scared to come out and I told her that for her, I was willing to be perceived as gay, or even to let people thing that I was "the woman," it wasn't enough. No matter how much I loved her, she couldn't hear me through the cloud surrounding her. I miss her, especially when it rains. But... it's been ten months, and I'm already 27 so, realistically, I can't just lay in a puddle of impossible wishes.
I have a date on Monday - my second date ever. And honestly, I'm kind of nervous. The woman I'm going out with is very nice, and she seems completely fine with going out with a guy who isn't read as a man very often. My last date ended with my first kiss and me dropping my date off and then calling one of my best friends and asking him if I was a horrible person for kissing someone I didn't love. I'm not *that* naive anymore but still, I'm worried. I'm worried that no matter how nice she is that I won't really give her a chance because I'm afraid. I'm worried that I'll fall into a relationship just because I'm lonely. And I am terrified. Absolutely
terrified that I will somehow hurt this girl. And I know that I'm not responsible for the feelings of another person but I can't help this feeling that I am, that it's my
job to make sure everything goes well and that she only ever has good memories from me, and I barely know this girl. I'm also worried that no matter how nice she (or anyone else I might date) is that maybe no cisgender woman will ever make me feel as much myself as I felt with my ex-girlfriend. It was so easy, so natural to be able to talk with her, and not feel judged or I don't know... I didn't feel like she expected me to be anyone but exactly who I was. I think that being with her was the first time that I understood that whole yin/yang dichotomy. Like, if she was the yin (dark/ feminine) side, and I was the yang (light/ masculine) side, but then I felt totally at ease with that yin drop on my side, and the yang on her side. Oh my God, I sound ridiculous... But whatever. I laugh at myself sometimes because it feels like she ruined me for cisgender women but at the same time, I'm equally attracted to them just less at ease maybe? (Of course, now that I've said that, watch all of the women on this site flee, haha. Ladies, you're totally safe. No more long-distance for me!).
I have no idea what to do right now or in general. I don't go anywhere to meet women, and I rarely flirt because I don't want to deal with what I dealt with recently when I forced myself to do speed-dating and within three minutes, was misgendered and laughed at (to my face) by four different girls... I'm not bad looking. I'm reasonably successful. But my personality doesn't suit most people, I don't think. I'm a serious person, and I like talking about serious things. I like other things but I never really feel comfortable enough to get to the point of expressing that. And I feel completely, hopelessly responsible for the people around me, and for not offending or hurting anyone. It scares me. I don't want to ever make anyone feel the ways that I've felt sometimes - I think that's what scares me more than anything. But I'm also lonely, and sometimes feel like there will never be anyone who loves me and whom I can love in return. And I want that, I mean, I'm only human. I want to find someone who shares my values and who wants to have a family with me but I sometimes really feel that that is impossible, not only because I'm transgender, which limits the number of people who may be interested, but also just because of who I fundamentally am as a person.
I don't know if I'm wanting advice or consolation or just to get all of this out of my system. Meh.