I was recently puzzling over why I was having such difficulty doing a  particular piece of writing. Everything I tried felt a little off key, a  little false, and I couldn't understand it. It slowly dawned on me that  the explanation was that I couldn't write authentically about the topic  at hand without setting it in a different and broader context -- that  is, without talking at least briefly about my feelings about  masculinity. I've written about masculinity before, but I've never  focused on my emotional relationship to it, so I set that post aside for  the time being and started to work on this one.
A short answer to the question of my feelings about masculinity is that they are complicated and deeply ambivalent. 
Complicated
Partly  my feelings about this topic are complicated because that's just how  feelings are -- their shape and landscape don't (and shouldn't)  necessarily follow the same contours as analysis. In particular, I mean  their tendency to seep from their point of origin, to transpose  themselves across similarity or resonance or homology such that the path  to get there makes a certain sort of sense but the attachment of the  feeling to the new object may not be obvious to those who have not  shared the same journey. For instance, we first hear a piece of music  during a moment of great personal joy and forever after it makes us feel  happy, or we have a terrible break-up and for the next two years any  sort of stress -- job stress, family stress, whatever -- triggers  sadness about our lost lover. Why this is relevant will become clear  below.
Partly my feelings about this topic are complicated  because masculinity is complicated, as is gender more generally.  Masculinity and gender as a whole can feel simple to some of us, but  once we start to pay attention to them, they really aren't. 
I  understand gender to be about how we move through the world. It is not a  classification of inert physical bodies, but rather is socially  produced -- that is, gender is an experience created as we interact with  those around us. Those activities -- ours and other people's -- do not  happen in a formless vacuum but are socially organized and regulated in  specific ways. Partly they are regulated by the behaviours of the people  we interact with. Partly they are organized by written texts that we  take up and act on, and regulated by the ways in which other people take  up and act on written texts. Partly they are organized by more  amorphous forms of discourse in the broader culture that we take up and  act on, and regulated by the ways in which such discourse is taken up  and acted upon by other people. Through these ways, through all of our  actions every day, gender as a form of social relation is organized and  created.
As I wrote a year ago:
Though there is lots of specificity according to social and geographical location, the dominant social organization of gender in North America involves two clusters of bodies, practices, and symbols. One (masculinity) is organized into relative privilege and the other (femininity) into relative oppression, in ways that are interconnected with and articulated through all other social relations. Deviation from the "normal" way of clustering bodies, practices, and symbols is also punished. The ways that gender gets done in the everyday lives of most people results in people getting trained as they grow up to enact in turn socially regulatory practices on the people around them, to enforce both m-over-f and adherence to the binary, though there are lots of other, more specific ways to understand how these relations are reproduced, including social organization mediated through official texts (e.g. immigration regulations, the organization of employment, etc.). Note that the ways in which those trained into dominant masculinities engage in practices that not only oppress women and gender non-conforming people, but are also part of how subordinate masculinities are kept subordinate. As well, none of us completely conform to the binary -- we have practices, preferences, desires, inclinations, tendencies that deviate a little or a lot from the enforced gendered "normal" -- and active social regulation (and, indeed, production) of people's practices, preferences, desires, inclinations, and tendencies is required to keep the supposedly innate binary from falling apart. Obviously, there is several library's worth of detail to how it all plays out in different situations.
Masculinity  is the body-symbol-practice cluster. Masculinity is the doing (and the  textual and discursive organization of the doing) that constantly  recreates the cluster. Masculinity is a way of moving through the world  by individuals that draws elements from that cluster and/or that is  regulated based on the content of that cluster.
As I've written before  in a slightly different context, there are elements of the  body-symbol-practice cluster of dominant masculinity, and of individual  ways of doing masculinity, that are innocuous, that don't matter. You  like pro football and drinking a cold one and using power tools?  Whatever, I like the middle one and have no interest in the first or  last, but if you like 'em, good for you. 
Some aspects of the  cluster can be positive, though even with these things it is all about  our relations with others -- for example, the imperative to exercise  material care for others that is prominent in some ways of doing  masculinity can be a great thing. It can be part of equal,  intersubjective, mutual relationships with family, friends, partners,  children. However, it can also be disempowering, controlling, and  downright misogynist, depending on how and in what context it is  enacted.
In both of these cases, various practices may be  innocuous or (potentially) positive in and of themselves, but all the  ways in which we treat them as "boy things" are still a problem and  still do harm -- the assumption that people who don't do masculinity  can't/don't/shouldn't do them and those who do masculinity can/do/should  erases lots of people's realities; the social regulation, the everyday  social punishment, when we relate to them in a way that is contrary to  gendered expectations, can be heavy and painful burden; and the ways in  which the actual doing of many practices occurs in gendered ways is a  product of the social relations that produce the two hierarchically  arranged body-symbol-practice clusters of dominant gender relations,  even if that actual specific practice and its distribution doesn't  matter very much. That is, saying that some elements of the cluster are  unimportant or positive does not make the existence of enforced clusters  any less oppressive, in the m-over-f sense or in the mandatory binary  sense. The clustering itself is harmful to people.
And, of course, there are  specific elements of the body-symbol-practice cluster of masculinity  that are inherently a problem, that are inherently about exerting  power-over and doing harm. Like, say, rape. Or taking what other men say  more seriously than what women say in interpersonal interactions. Or  allowing your inertia and passive-aggressiveness and learned  helplessness to keep your female partner doing far more than her share  of the housework. Or lots of others. A few men do some of these, a lot  of men do others, and saying all of this is definitely not claiming that  "all men do X." But each of these oppressive practices is in part  produced by (and reproduces) the body-symbol-practice cluster that is  masculinity, and none of us who do masculinity can claim that the logics  and processes that produce them are nothing to do with us, even if we  don't ourselves do that specific thing.
Masculinity, therefore,  is complex and heterogeneous. Any particular enactment of masculinity  might be very different from another enactment, both in the sense of one  person doing masculinity differently from another person but also from  one moment of masculinity-as-practice differing from another moment even  when it is the same person doing them. That's one level of the  complexity. It is made even trickier by the fact that all of these very  different experiences of masculinity are connected in material ways  --that is, the relations which socially produce them are woven together.
So  it makes sense for our feelings about masculinity to be complicated,  since masculinity itself is complicated. After all, masculinity is not  one kind of practice but many different practices and all of the  experiences that those practices can create. There is no timeless  essence, but rather a contingent, socially produced clustering of  disparate elements that shifts with time and place. Yet that clustering  has material reality, because it is reflected (in diverse ways) in the  practices of lots of people. Just because there is no inherent, natural,  or inevitable connection among the elements that are clustered under  the banner "masculinity" doesn't stop our regular experience of that  clustering in the behaviour of other people from having an effect on our  own consciousness. And the tendency of feelings to transpose themselves  in non-linear, unpredictable ways adds a further layer of complication.
Ambivalent
I  should start off by saying that the deep ambivalence I feel about  masculinity is not the sort of ambivalence that would ever result in me  adopting a way of moving through the world that would cease to be read  as masculinity by the overwhelming majority of observers. I am cis, not  trans. My way of doing masculinity may be quirky and against-the-norm in  some moments (though in other moments it is entirely consistent with  dominant ways of doing masculinity), and I may see the deliberate adoption of ways of moving through the world that challenge dominant ways of doing masculinity  as an important political strategy for bioboys with critical gender  politics to adopt. But however strong my negative feelings about the  stream of doing, the cluster of bodies and symbols and practices, that  get labelled "masculinity," it is and will remain the sea in which I  swim.
Yet I have a lot of negative feelings about masculinity, for quite a wide range of reasons.
I  have been hurt and damaged by the social regulation that organizes the  clustering of practices we call masculinity, and that patrols its  borders. All of us who do masculinity have felt that. Even Erving Goffman's "unblushing male"  -- that is, a doer of high-status masculinity that meets the  requirements for what a man 'should be' -- has moments of not fitting,  moments of feeling the need to exhibit emotion that men are told we  shouldn't, moments of not being tough enough, hard enough, angry enough,  dominant enough. It happens to all of us, even if we want to fit, even  if we don't have the tools to articulate that the social punishment we  receive for not fitting is a source of pain and is wrong, even if we are  among the most enthusiastic at doling out punishment to other men when  they deviate from dominant norms of masculinity. From the moment of pain  in the hockey locker room when peers deride you as not being man  enough, to the long-term stunting of connection with your own emotions  brought on by relentless policing of emotional expression by others and  by self from a very young age, the regulation that creates masculinity  is a source of pain and damage for those of us who do masculinity. This  informs my feelings about masculinity.
I have also been hurt by  specific practices or tendencies or actions that are part of the  masculinity cluster that are not directly about pushing for conformity  with dominant ways of doing masculinity. In some contexts, men do  masculinity in ways that involve aggression towards others, or involve  treating those seen as subordinate in hurtful or disrespectful ways.  Such behaviour isn't unique to men, and can be associated in different  ways with different kinds of privilege. But it is a common element of  body-practice-symbol cluster of masculinity, and is part of how many men  do masculinity. Again, all of us have been on the receiving end of this  in one form or another, and all of us have been hurt by it. As a  relatively privileged man, this has impacted me less than many other  people, but it has impacted me. So this, too, informs my feelings about  masculinity.
Moreover, people I care about have been hurt both by  the punishing regulation that patrols the doing of masculinity and by  the various common practices of masculinity that are acts of domination  of men over women, straight men over queers of various genders,  gender-conforming men over gender non-conforming men, higher-status men  over lower-status men. People I care about have been bashed, raped,  assaulted, emotionally abused, disrespected, dehumanized, talked over,  erased, mocked, harassed, and otherwise treated unjustly where those  actions have been organized and enacted, in whole or in part, through  masculinity. As above, I'm not claiming that all men do these things or  that only men do these things; rather, I'm claiming that these things  are often socially produced in ways that are grounded in masculinity.  And this plays a huge role in shaping my feelings about masculinity.
I  have also done things that I regret, and some things that I am ashamed  of, that are related to my training into masculinity. I mean, I've never  done the worst things that can be produced in part through training in  masculinity, but I've done all of those everyday things that most of us  who learn masculinity from infancy do from time to time, from making  sexist assumptions, to talking down to a woman or a supposedly lower  status man, to falling into looking at some random woman's body in an  intrusive, objectifying way. I think I engage in everyday oppressive  behaviours rooted in my training in masculinity less often than I did  when I was younger, and I hope I'm more open to being called on them,  but I still sometimes do them. And I find that upsetting, and my  emotional relationship with masculinity is certainly informed by those  feelings.
So it is no wonder that there is a sizeable dose of negativity in my mix of feelings about masculinity.
Feeling It
So.  I encounter some action, some practice, some utterance, some media  product that I know flows from or is related to the body-symbol-practice  cluster that is masculinity.
Most of the time when that happens,  I don't actually have a noticeable emotional response. None of us  could, I don't think, given how pervasively gendered our experiences  are. We can't notice everything, we can't always dissect out the impact  of gender (especially on the fly), and we can't really react to  everything that we notice.
One consequence of that is that there  are probably lots of little things that really do matter, in the sense  of enacting troubling or oppressive aspects of masculinity, that I don't  see or don't react to, both in my own actions and in those of other  people around me. If you really pay attention, troubling gender stuff  (most of which is related to masculinity in one way or another) is  really, really common in our everyday experiences. 
It's not just  a matter of how the volume of things there you could react to, though.  Those of us for whom being on the receiving end is relatively rare and  mild and for whom gender privilege is an everyday reality, there is  little incentive to notice and lots not to notice, and less reason to  have an emotional response when we do notice. Seeing and feeling are  heavily influenced by privilege, and it takes ongoing work to counter  that. I see more than I used to, but I know I don't see everything.
On  the other hand, enactments of masculinity that I do notice and that  have sufficient emotional content for me to have an emotional response  are more likely to be things which are oppressive and therefore things  which evoke negative emotions in me. This is true in the moment, and it  is also true of more sustained emotion about particular patterns and  tendencies that show up in the doing of masculinity. As well, because of  the tendency of emotions to transpose in ways that do make sense but  not necessarily the same sense as, say, an assessment of what causes  harm and what doesn't, there are instances where I have negative  emotional responses to elements of the masculinity cluster that don't  really deserve it.
One interesting impact of this emotional  ambivalence about masculinity is that, in my case at least, it has  reinforced in my own doing of masculinity a particular element of the  cluster that is very common and that is not at all a good thing. That  is, I find it harder to cultivate substantial connection with other  people who do masculinity, particularly bioboys who have no interest in  critical gender politics, and I am, quite frankly, less inclined to try.  And this is on top of being quite shy and reserved to start with. So  almost all of the small number of men with whom I feel some  important-to-me connection do masculinity in some (though never all)  ways that run counter to dominant norms, and many are political  radicals, queers, trans, or some combination. It's not that I don't know  that it is politically important for men to cultivate substantive  connection with a much broader spectrum of people who do masculinity --  any collective critical gender politics has to involve men connecting  with each other, challenging each other, and supporting each other as we  act in and support struggles against gender oppression. But...well, I'm  working on it.
The Positive
Sometimes,  though, I encounter some action, some choice, some practice that is  clearly part of another person's way of doing masculinity, and I feel  inspired, challenged, enlightened. It doesn't happen often, mind you,  and as with the negative, most of the moments that theoretically might  evoke such a response do not, in fact, do so.
For instance, above  I mentioned the fact that there are practices that are part of dominant  conceptions of masculinity and that are, in and of themselves,  innocuous or (potentially) positive. Encountering those kinds of  practices rarely makes me feel much one way or the other.
There are also the countless little moments of refusal that I know  are part of the everyday lives of all of us who do masculinity. It's my  understanding that all of us exist in the context of oppressive social  relations in a way that is within, against, and beyond them. In the case  of social relations of gender for those of us who do masculinity, we  all have moments where we refuse to "act like a man" or at least "like a  real man is supposed to," where we instinctively feel the ways in which  our possibility or the possibility of a loved one is limited if we go  along so we just don't. Even the biggest multiply-privileged patriarchal  jerk has tiny moments of everyday refusal like that. Often we don't  recognize them in ourselves or in those around us, partly because they  are often small enough that they are hard to see but also because part  of our gender training is, I think, not to see such moments of  resistance. These moments are crucial, and part of cultivating critical  gender politics among people who do masculinity is to connect with those  moments, nurture them in each other, help them grow and become explicit  and collective. Nonetheless, largely because of how hard it is to see  them, this kind of moment is rarely a source of positive feeling for me.
No,  the actions, the choices, the practices that give me positive feelings  of various sorts are usually those that are more overtly, and often but  not necessarily more consciously, counter to dominant norms of  masculinity. It can be as simple as seeing a dad parenting in a tender,  nurturing way, especially if I detect some kind of explicitly  pro-feminist edge to it. Or it might be witnessing a moment of genuine,  tender emotional connection between men, especially between straight  men. Or it can be like a moment I remember from an Ivan Coyote  story in which the viewpoint character and a friend, both women,  overhear without being observed a working-class father passing values of  genuine respect for women on to his adult son. Or lots of the  subversive, delightful choices of people I know who are somewhere on the  transmasculine spectrum. Or lots of other ways in which men visibly,  deliberately don't do what they are supposed to do -- the visible and  non-utilitarian enjoyment of some "not a guy thing" thing, the  unexpected refusal to just accept a sexist comment from a fellow man,  all that kind of stuff. 
That is, my reactions to masculinity are  at their most positive when it is masculinity that is being done in  ways that -- intended or not -- act to directly subvert m-over-f and the  mandatory binary, to oppose the ways in which those those relations and  the practices which produce them harm so, so many people. 
Which  sounds cheesy and maybe even made up -- like maybe feelings invented in  the service of performing a particular politics. Which it isn't. In  saying it, I'm not claiming any particular success in doing the kinds of  things that give me positive feelings, or at least not nearly enough,  and I'm certainly not claiming that I never do masculinity in all those  ways that are the basis for my ambivalence about it. By the very  complex, heterogenous, socially produced way in which masculinity is  enacted by those of us who do it, we are all a mix. And as I said,  overcoming the ways in which my own reaction to that mix often prevents  me from forming productive connections with others who do masculinity is  part of my journey. But even so, it is the kind of counter-normative  moment I've just described that gives me hope, gives me positive  feeling, when it comes to masculinity.
Reprinted with permission from Scott's blog, A Canadian Lefty in Occupied Land.