Thank you!

>I have some experience with transgender people because a friend of mine from the past transitioned from a man to being a woman. This was confusing for me for sure because I was relating to her as a woman and I just thought she liked men. But it turned out that she liked women, and I began to feel uncomfortable. I believe she had a crush on me. This was not really welcome because I am a straight woman. I am not attracted to women at all.......I think this was potentially the most confusing experience I've ever had. I began to distance myself from her because I was not interested at all in a romantic relationship.

This can be a confusing time for all parties involved. There are parts of our language and labeling system that break down here, making things very difficult. While I can't speak for the transwoman you knew, I might be able to relate. 

Before I had started down the transition path, I would dress as female and go to certain friends homes to hang out. One of these friends was a girl who identified as a lesbian. Now I will freely admit that while still feeling lust periodically towards people, the ones I was interested in were those who I honestly felt a connection with (pansexuality.) This connection was built up stronger with her over this period by just being able to hangout, talk, or play games while I presented as female, and reaching the point that I felt I 'liked' her. Eventually I told her about this and while for me a simple 'I don't feel that way about you' would have been more than sufficient and I would have left it there, she was the type of person that couldn't give 'bad news' and basically danced around the issue.

A couple of points here. First, there is a tendency for people to not give 'bad news' because they don't want to hurt somebody else's feelings (which is understandable) however communication breaks down very quickly because of this. The 'nice' answers didn't give any true information (like I don't want to be with anyone right now, maybe later) and over time come in conflict with observed behavior (she dated somebody, which was fine, but that countered the statement of not being with anybody right now.) When we are truly connected and care about somebody, while hard, the best thing is to be honest. 

Second point here is that in my head, I was beginning to consider myself as female, which meant being with another girl would equate to a lesbian relationship. While logical, this didn't necessarily translate into how my lesbian friend 'felt' about it. Honestly, I don't think that she had any sort of ill will towards me, but I don't think she would have considered the two of us being together as a lesbian relationship. This is not meant to bash her in any way, it's merely a case of our 'shared' language completely breaking down. A explicit conversation is necessary to define each individuals take on what being gay or straight is when a transgender person is thrown in the mix. So much of this is personal feelings and perceptions. 

Now specifically on your experience. I can understand the uncomfortableness of feeling of the transwoman had a crush on you. Honestly I think this same feeling occurs when anybody of any gender appears to have intimate interest that is not reciprocated. It basically creates an 'Elephant in the Room' situation where everyone knows it's there, but it's not talked about. While I'm not saying anybody was in the 'wrong,' because we just feel what we feel on matter like this, I recommend at least trying to discuss the issue with her. I don't know if she is like me and really is ok with a 'I don't feel that way about you' answer. This conversation also tends to lead into both parties defining their stance on personal preferences and views, which I feel are necessary. For me that gives me understanding and closure, even if not the answer I was hoping for. No relationship can last for long when always 'walking on egg shells.'

>I feel that I am on a spectrum of being female that does not identify with the traits that society holds as being female. I am a very strong person in many ways, and I find myself quite at home among males. I have worked in male-dominated spaces, and even though I dislike them for the most part, I can generally hold my own, and I don't feel threatened by men.

This hits the nail on the head as far as part of the issue. I view gender as a feedback loop between my 'essence/homunculus' which feels feminine and the way society treats me. When the to match, positive reinforcement occurs, when the don't, negative reinforcement. I truly think that if I were not to come in contact with people, the concept of gender is moot beyond 'I am what I am.'

Society has depended on the gender binary for long time, even so far as embedding itself deeply in language. Many don't even have the concept, let alone the words, for dealing the the infinite shades of grey between black and white. I see this as a problem ALL people have to deal with on some level, since we are all some shade of grey. They key here is to shuck the labels, as you have done, and find what works for each of us individually. 

While people talk about the difference between men and women, it's often forgotten that while looking at averages, these differences can be true, the variance of each group in reality have a huge overlap. For example:
https://perrystreetpalace.files.wordpress.com/2012/09/usmenandwomenheight.png

In this height chart, we can see that men are on average taller than women. And statistically speaking this is true. However we also see the huge variance that easily allows many women to be taller than men. This sort of scenario is common and often overlooked across the board. There may be tendencies, probabilities and averages, but in reality every situation boils down ONLY to the individual in question. All too often it's assumed a woman is or should be yada yada yada and a man is or should be yada yada yada. We'll be in a much better place when society as a whole recognizes the huge scale of individual possibilities and do away with such assumptions. Unfortunately, people like things that are nicely packaged, easy to deal with, that don't cause them to actually think about and analyze the model they are creating for another person.

>So, this translates into me not identifying with the female sex object role model, and it also results in me not wanting to draw attention to myself. I'm not gay by any stretch of the imagination, even though, there have been times I wished I was because of the grave fear of pregnancy. Many lesbians have confused me for being gay because I generally don't wear makeup and I don't wear fussy clothes. I dress kind of in a gender neutral way. I do, however, like to play dress up and sort of play around with female personalities. I like being dramatic and creative in making up female characters.

Biology plays a strange roll in all of this, which I view as coupled yet distinct from a persons essence. While I understand the  'lustful' drives of men, I feel women are often viewed purely in the biological sense sometimes. I don't think most men truly understand what it's like to have the stares, the looks, the pick up lines, or the creepy stalker. I don't mean to speak badly of men here, most truly seem to try and understand, but unless you are in it day after day, the true impact is lost.

The other part of this is that talking about sex or gender in general is really a taboo in American culture, which I find ironic because we are inundated with Sex Sells advertising constantly. There seems to be a social pressure to feel bad when not fitting into a nice category (which in essence doesn't exist with everyone being on the spectrum versus the extremes) which also inhibits conversation on the issue. Nobody can tell me how I FEEL, and I can't tell others how they FEEL. The ability to self reflect and then communicate ones own sexual orientation and gender identity is crucial in my mind. To me this doesn't change the essence of the matter, but rather acceptance and opening of communication. I truly hope to see society begin to shift away from thinking and speaking only in binary.

>For all these reasons, I feel kind of odd, like a true eccentric. I don't have a strong one-dimensional way I present myself. It's like I have a private identity that is creative and feminine, but I don't want to show it to the world...

When people first meet me and are looking for good description labels, I like to always start with 'I'm complicated.' Who and am and what I think can't fit onto a bumper sticker.

I truly believe every person lies in a unique area on the multi-dimensional scale of personality, preference and pre-disposition. This is something that any body (in my mind) HAS to have some concept of, even if subconsciously, to truly feel happy. 

I honestly think that everybody has what I term 'actual self' and a 'social self.' The actual self is just what you would think, completely free, sing while nobody is listening sort of [Flow state.](https://en.wikipedia.org/wiki/Flow_(psychology)) The social self however is more difficult, there are things we self censor for good reason (for example not using curse words around kids) and those we feel are externally imposed, typically not in accordance with the social self. I can understand the 'private identity that is creative and feminine, but I don't want to show it to the world.' I see this as a defense mechanism of sorts, like deciding (subconsciously) to not show certain emotions after getting picked on. Often the goal when deal with the public isn't to connect or grow, but rather to be left alone. This is a sad fact in my opinion that I truly hope to see change over the coming years. 

I do still think that in an ideal world there will still be a private, non-public self. For example I don't like to practice new things on my drum in public, instead prefer to show off the things I've already 'mastered,' which I'd expect is common across many others.

>And my sexuality has caused a lot of issues too. I am a straight woman, but I have some problems with intimacy. For many years, I sort of viewed my sexuality with disdain, I had a lot of guilt. It is for these reasons I feel that gay men are drawn to me, because in many ways our struggles are the same. Many gay men feel comfortable being themselves around me because of our shared difficulties in dealing with the male sexual relationship....

Some of this I touched on in the previous section of this reply. However, I will say that I feel the guilt is an effect of social pressure, framing and priming us. For example, imagine a woman walking around Missouri while topless...oh the stares, the lust, the disdain...soo many sensitized emotional reactions, because it's not something we think of ofter nor socially acceptable (regardless of right or wrong.) Now imagine a (non-white/cultural norm color) woman being topless among the Dogon tribe in africa, where it's the norm for women to be topless. The men don't lust constantly for them and nobody thinks anything of her breasts being exposed. 

My point here is that we a shown concepts of 'normal' and what is socially acceptable through parents and media, later being tested and refined more in school and non-family socialization. These concepts of what are acceptable or not are framed early on and primed as we go along, usually leading to feeling of shame when we feel we don't fit. This unfortunately only leads to 'society' being reinforced in it's normality, which really is just a show that causes us to become separated from each other. Don't we really judge people by who they are in essence and not the facade we present to society or Facebook?

To touch on the last part here on feeling comfortable with gay men. I think you are spot on that you are able to connect with gay men through shared experiences. That is really what any relationship, group or family are founded upon in my opinion. They understand what it's like to date men, I'd assume know where they fall on sexuality and identity spectrums, etc... that help for form that core connection. I also suspect that part of this being easier for both you and them is that the feeling of sexual attraction is completely removed. The walking on egg shell scenario commonly occurs due to questions of 'do they like me?'

I think I answered everything. Just let me know if I missed anything or would like clarification.

Great reply, questions @stellabelle! :)