after having so many experiences with people intentionally trying to invalidate my gender or reassure themselves of their perception of it by calling me pretty, putting down my name, etc etc...  I've got to the point of being paranoid about it with just about everyone i meet.  I only pass maybe half the time, more or less depending on what kind of people I'm around and little details that are subject to change like the condition my hair is in or how my voice is doing..  so I never know if people are trying to "clock" me and being passive aggressive, or just honestly misgendering, or neither.  like today, a kid at work said "i like your name, it's pretty." my name is Kenny.  not exactly a fancy or feminine name.  I wasn't sure what to make of that.  I've seen kids' parents put them up to saying some rude things, so while I try not to over think stuff like this, sometimes I can't help it.  how do I deal with this constantly feeling like or wondering if people are trying to be hurtful?  it's not like them doing so would even hurt me, but having the whole gender/not passing thing rubbed in my face all the time really messes with me.

I wonder if you are taking it the wrong way? Having your name called pretty sounds like a compliment to me. I found that at least for me, I was (and am) my own worst enemy when it comes to judging myself.

You have to rationalize that these people don't care or think about it as much as you, and you caring and thinking about it as much as you do isn't helping you. They aren't going home and losing sleep over it. They probably aren't even aware half the time of what they're saying. For you to be as sensitized as you are to it has no benefits when it reaches the point of paranoia. The only one losing is you.

Digesting and accepting this is important to moving on from paranoia and relegating your sensitivity to situations that are more useful. Such as where you might be in danger.

At the end of the day paranoia is a problem mind state for a reason - 99% of the time it's unfounded and all in your mind. I don't know how well you pass at the moment or how long you've been on T but you need to be reasonable with whether or not you do actually pass well, and if you don't, there is no point blaming the rest of them for not being savvy enough to say what you want to hear. Unless someone has been explicitly told and is deliberately ignoring your requests, it's to be expected you will be misgendered until you sound male and look more male by the average person on the street. Not what any of us typically want, but reality.

If you have mental energy to spend on this, then spend it on figuring ways to further your goals and your desires than on whether or not other people are conforming to your wishes. We can't control the world, but we can control what we do and how we do it.

It's not like I'm putting off doing or planning real life things to sit and worry about the ->-bleeped-<-ty treatment I've gotten from other people..  but when someone makes a comment that seems out of place, or seems to be using an unusually high amount of gendered language, or putting emphasis on those things, it makes me feel like they're doing something on purpose.  because a lot of people do/have done exactly that, with the intention of upsetting me or putting me down.  and some of them go from passive aggressive to outright aggressive very quickly if you do anything other than agree with them.  I don't feel safe correcting people, especially if I can't tell for sure what they're doing.  and it's not always knowing whose intentions are benign and whose aren't that has me constantly on edge.  I'm not complaining about being misgendered accidentally by people who don't know any better, if that's what you got out of my post.  sorry if I was unclear.  but for all i know, I could be in danger because people are never up front about things and they can escalate in an instant if I'm not careful.

In that case don't bother correcting them. I didn't. I couldn't have given a toss if they got it right or wrong or what they believed about me. I knew where I was going and what I was doing and that was all that mattered. What makes them deserve the information about you, anyway? What people don't know can't come back to bite you in the ass, I say. Know what I mean?

If they're saying stuff to try to extract information so they can be even more aggressive then don't give it. I'd just act like whatever they're focusing on was misheard or glossed over, if it just means more trouble for you to respond. If you are in a potentially dangerous or aggressive environment then I'd play the innocent about their concern till you can get out of it. I volunteered nothing until it was plain as day what was going on, and until that point people thought whatever and usually just made up some idea in their own heads I suppose to explain their curiosity. You're asking how to deal with it - so that's how I'd deal with it... give them nothing to chew on or get their teeth into if that's how they're gonna be. Ignore it, act like whatever it was went totally over your head, or give them a fake smile of ignorance... whatever you feel like, but make sure it's non-escalatory, if confrontation is your concern. Goes without saying as well that if these people - whoever they are - can be avoided then avoid them.

That's what I do, generally speaking, and I have avoided confrontation except with those who force it to happen by not letting up.  but not saying anything to anyone has its own problems where my emotional well being is concerned.  I guess there's just no winning anyway.  I appreciate your response, even if I'm being difficult. 

Guys tend to shy away from receiving compliment like "Pretty".  You're "Cute" is okay, but Pretty is too feminine for most guys.  And cute is pushing it sometimes.  Years ago and a lot of pounds less I was told by a woman that I had a cute ass. 

I still tend to blush at compliments - just never geared or trained to accept them.

pretty in particular is one that people use with the specific intention of invalidating me, since it's used almost exclusively for women.  I am especially loathe to hear that one.  even when it's not meant maliciously, then it just means not only am I being read as female, but as an especially feminine one. and that's exactly what hateful and instigative people want to convey, twisting otherwise benign statements into insults. they do the same with things as small and subtle as using gendered language, hence why now I have an extra layer of discomfort about being misgendered--because while it may just be that, it might also be something worse.  so not only is dysphoria ramped up to 11, but I'm lowkey afraid one of these days I won't be able to avoid confrontation and who knows where that could lead? 

That's unfortunately one of the problems any of us might face. I have a hall-sharing neighbor for example who - if she figures things out, could be not only difficult but malicious. And she's got a very large son who's about as subtle as a brick who would probably follow her lead. I'm really not sure how things will go with them and there's not much I can do in that scenario other than be ready to move somewhere else. Someone like that pair could spread rumors around the whole place if they wanted to or worse. Still, if that does ever happen, I will just look to leave the building or immediate area. I could also be completely wrong about them, they might be fine with it and I might just be judging them too harshly. But it's the reality of the situation.

The same could happen with my landlord one day if he happens to feel like being a dick about things. I just have to be prepared and ready to deal with it if that happens.

As a former one myself, all I can say is welcome to "Manhood" where you have or at least I had to be on guard 24/7 and ready to respond.

One of the nice things of MTF'ing is that while it's difficult to shed one's self of the "Guardian" mentality, it's nice when it's not sooooooooooooooooooo pronounced.

Interesting thread. However it's a bit unclear to me who these 'people' who misgender you and hint you're female, are. Your family members? Friends? Coworkers? People you go to school with?

Who says you're pretty? People you don't know well? Acquaintances? Are they people who know you're trans? Or people more close to you?

I hate being called that myself. I remember once my mom saying that to me plus similar stuff to make me annoyed or, in her mind, just being 'nice' meaning trying to be an ass and completely disregard my gender. But then my family members are a piece of work in general. I already know they don't accept me so I spend minimal time with them.

My advice:
With strangers - just disregard. I know it makes you feel angry, but you also know they don't mean no harm
With acquaintances - politely correct if possible. Or avoid if that's not worth the trouble.
Friends etc. - demand respect. Choose your friends more carefully I guess...
Very close friends, family, etc. - extra demand respect!!! There's no excuse for their behavior!

Just saying that... do you need to see these people if their presence makes you feel bad?

Or did you mean just in general - that you hate not being automatically read as a guy and treated as such? You know the general trans paranoia thing? Wanting to be one of the guys but not really being/accepted etc. etc.?

I'm sure you must be able to find friends and people that are cool with being LGBT and can hang out more with them instead  .