One short and sweet observation:

[Call me Jess]

I only seem to consistently "pass" when I'm at my most andro.  I'm talking like flare cut jeans and a t-shirt, Chuck Taylors, a bandana tied around my head and my hair mostly stuffed into a ball cap.  Seriously, I don't think I'm capable of looking more boyish.  I mean obviously, if I'm in the gayborhood, that might be expected, but this happens everywhere.  Any thoughts on this?  It just seems kind of weird to me.

[Vincent E.S.]

I pass the best when I look andro too. I think it's because when I'm somewhat androgynous, people perceive me as a somewhat androgynous or feminine male, whereas if I'm trying to look manly, then there'll just be something... 'off' about it.
So maybe they're just thinking of you as a somewhat androgynous/masculine female?
Lots of cisgirls I know dress that way.

Based on the comments people have made to me in past years, being all done up in makeup and skirts would have you pegged as ">-bleeped-<" faster than a more subdued/casual appearance, which would look more natural. But that could just be the people who said those things.

[Call me Jess]

Well, it might be optimism saying people perceive me as a masculine female, or pessimism saying people perceive me as a feminine male, but I'm sure both happen.  It crossed my mind that the typical rude loudmouths probably aren't clocking me when my presentation is androgynous because I don't even catch their attention.  This could skew my perception on the matter, as that's not really "passing", per se.  Still, I get called ma'am most consistently when I'm at my most boyish, which seems counter intuitive to me, no matter how I look at it.  This might be a controversial statement, but maybe I just look like a butch lesbian (I really do believe there is dimorphism between lesbians and straight women in many, but not all cases), and when I dress appropriately for that, it just works.

[Vincent E.S.]

It's possible, nearly anything is, after all. I'm gay, so as long as someone knows that about me, any femininity usually gets chalked up to that.
Your [good grief I just forgot the word] picture doesn't look butch though, just not ultra-feminine. Is it worse to be thought of as a man, or a very butch lesbian?
I think you're right about androgynous presentation in general not catching people's attention. That's probably part of why it's easier to pass- people aren't examining the details as much as usual.
When I'm specifically trying to be androgynous(like when around extended family), I'm apparently really androgynous and it does draw attention; many strangers avoid using any pronouns whatsoever because they can't tell. But the people who don't look at me closely enough to be confused just assume that I'm male.

[Call me Jess]

Actually, I'm totally cool with being regarded as an androgynous dyke.  It's about as close as I can get to identifying myself on the spectrum in a couple of words.  Your experience seems to mirror mine completely, just in an inverted fashion.  I notice customer service greeting people with "sir" or "ma'am" and sometimes, when they get to me, it's a much more ambiguous, "What can I get for you today?", or something to that effect.  Kudos to them for rolling with it, you know?  I can appreciate that it may be an awkward position for them to be in, so it means something to me that they seamlessly get through the exchange without either of us feeling weird about it.  I used to get called one or the other seemingly randomly, but in the last few months, it's most often ma'am and occasionally just confusion.  I can't complain.  Uncertainty is an upgrade from being seen as male in my book.

[Gravity Girl]

You tend to pass better when you're comfortable and it sounds like you're comfortable doing the whole andro dyke thing. Me I swing between the whole andro dyke thing and being quite femme and have started describing myself as a very femme tomboy...heck, it works for me.

[Call me Jess]

It's good to hear from people who can understand the concept of a person being butch/femme variant independently of gender expression.  I spent many years being socialized into masculinity.  It's a part of who I am, and I have no intention of subduing or denying it.  At the same time, it doesn't have to compromise my femininity at all.  It took a lot of personal growth to get to the point that I can understand and appreciate this.  Having yourself figured out is a gift.

[Vincent E.S.]

Last time I went to the skating rink, I went with a close friend who happens to be a girl. We were the only two people  in there. When we got our skates, the employee handed a pair to her and said, "Here you are, missy!" When he handed me mine - "Here.. uh, buddy."    The confused look on his face was priceless.

Once I realized I what I am, I tried for quite a while to suppress anything remotely feminine about myself. I've lived my whole life in a very conservative state, so though masculine girls are somewhat tolerated, feminine boys get a lot of flack because they're "not normal." But hey, no one is normal!
It's actually been fairly recent that I've felt comfortable enough to swing between masculine-andro male and feminine male.
How long did it take you ladies to accept that aspect of yourselves?

[Call me Jess]

I'm not sure it was time so much as events that triggered it.  When I had to re-enter the dating scene, I realized authenticity was paramount.  That's when the real me just kind of floated to the surface, you know?

[Vincent E.S.]

That makes sense. I've never dated anybody because I'd feel like I was lying to them, since everyone interested in me thought of me as a girl, it wouldn't really be fair to suddenly say that they were actually dating a boy.
Though if it's a serious relationship, it should be with someone with whom you are comfortable being yourself, and that can't happen if you're hiding a very large part of yourself. I don't think my mother understands that, though.

[Lyric]

This could be a signal that you need to tone down a bit when you're trying to pass. Think about it. Most people wear the same clothes these days-- jeans or shorts and a t-shirt (or something close). Gender is often distinguished in the details-- walk, voice, facial hair (or lack of), jewelry, and chest bumps. I dress very andro most of the time, but sometimes get wolf whistles or honks when walking down the street. My slender silhouette, longer women's hairstyle and manner apparently make me pass without trying-- from a distance, at least. With a bit of makeup & basic fem clothes I seldom get a second look.

[Call me Jess]

Vincent - I'm just honest up front.  There's no sense in dragging it out.  The worst thing that could happen would be for you to really get into a meaningful relationship with someone only to have it all come crashing down when you come out with it.  It's an unfortunate fact that some people that are probably otherwise great just can't reconcile themselves with dating a trans person.  Luckily, there are plenty of people that it doesn't bother at all.  It can be tricky to find a good partner, but they're out there.  I'd implore you to cautiously give dating a try.  A good relationship with a person who understands you is a very enriching experience and helps you to learn more about yourself.  That's what life's all about, right?

Lyric - I can't think of much worse than having to make a concerted effort at portraying myself in an unnatural way for the rest of my life.  The concept of "trying to pass" sounds like hell.  The whole point of transitioning for me was to allow myself to act naturally.  (I know it's not like that for everyone, and they certainly have my condolences.)  The only thing I can do for myself that I'm not putting enough effort into is my voice.  I'm completely confounded in figuring out how to sound, because it comes off ultra-girly and that's just not me.  It makes me feel ridiculous.

I'm convinced my problem is bone structure and too much forehead.  I'll let you know conclusively sometime next year.  :-)

[Vincent E.S.]

You're right. The problem is that I'm in an exceptionally tiny private school that sucks. Seriously, counting all the students there from 6-12 grade, there are only 179 students. So, for one thing, nobody sees me as the male that I am, but I guess that since I'm actually a gay man, I've just always felt that it'll be impossible for me to have a serious (to the point of sexual) relationship with anyone who's not bisexual.
Also, nobody there is attractive, physically or personality-wise. There's only ever been one guy I had a serious crush on, but he lives on the other side of the country from me and he's straight.

I guess I'll just wait until I go to college to start dating. I've waited this long already, what's two more years gonna do?

[Call me Jess]

Yeah, that sounds rough, Vince.  It was presumptuous of me to think that everybody has an enormous community to pick and choose from.  I've lived in the heart of Dallas for five years now, and there are roughly six million people within a 100 mile radius, so I might be spoiled.  If two more years is what it'll take to get out of there, I guess all you can do is keep busy and do the best you can until graduation.  There are plenty of very liberal college towns all over the country.  Shop around if you have the opportunity.  I've noticed that FtMs tend toward technical brilliance, so I'm sure you have a bright future ahead of you.

[Vincent E.S.]

Eh, it's only natural to assume things based on one's own experience.
My mother found a list of colleges that tend to be particularly trans-friendly, especially with student insurance, and one of them was UC, which I was already considering looking into. I'm definitely choosing a college based on (in order of importance) culture, size, and climate.
I think technical stuff runs in my family, my dad's an electrical engineer. But he thinks large books titled, "The History of Salt" are not boring. I like to think I'm somewhat more exciting than he is.

I'm just curious, and you don't have to answer if this is in any way uncomfortable or insulting, but did you date people before you came out or transitioned at all?

[Call me Jess]

"But he thinks large books titled, 'The History of Salt' are not boring."

That's a really funny example.  You write very well.  I find myself wondering how old you are.

The question about dating pre-transition isn't uncomfortable or insulting at all.  I'm always willing to share my experiences with people who have a genuine interest in hearing them.  I had three or four substantial relationships (longer than a year) pre-transition, and was married once.  In spite of a protracted and incomplete puberty, I still managed to have high enough T levels to function as a straight, cis-gendered male for a long time, so in this period, I never had to reconcile being in heteronormative relationships with being transgender.

Does that cover the bases?

[Vincent E.S.]

Thank you! I'll actually still be a minor for a while yet, but I've grown up in a family that took weekly trips to the library, so my brother and I tend to have a better grasp on grammar and vocabulary than many people our age.

A very complete answer, thank you. I can't imagine myself trying to be in a relationship as a straight girl. It would feel like insubstantial and shallow. But then, we all have different experiences.