Oblivious allies

So I've been dwelling a LOT lately on the allies in my life, how they do/don't support me and others that are targeted by oppression. I have an incredibly difficult time identifying with targeted peoples, I was raised to work hard and keep your chin up, don't complain and whine about things you can't change, good people get what they deserve in life, we are not of this world anyways right, yadda-yadda, etc. Basically, these are fucking excuses for internalized oppression (for targeted people) and internalized superiority (for privileged people). I'm a woman from a rural area that largely consists of middle-to-lower class people, the vast majority of which are blue-collar workers. It's strange to be partially targeted and partially privileged according to which aspect of my identity one is referring to. I'm a woman, but I'm white. I'm from a lower-middle class home but I'm straight and cis-gendered. This leaves me dual roles as both ally and targeted person. And I bet you can guess which one I feel most comfortable identifying with...

I am not the BEST at acknowledging my privileges in life, I'm much better at it than I used to be, but it's a constant struggle to keep that shit in perspective. It's important that as an ally to women (and men) of color, lgbtq peeps, working class folks, etc, that I respect the different forms of oppression they face that I am completely exempt from. Yes, some allies do get flak for standing up for targeted peoples, BUT that is NOT oppression. That is the price allies occasionally pay for going against systemic oppression, whereas targeted people pretty much always deal with that crap.

I have a friend who is a white straight cis- male from a middle/upper-middle class background (he claims his parents don't make that much money, but I've seen their giant house and both of them have college degrees, and have invested money in his name... sooo ya). As one of the few male friends I have right now, and one of the ONLY close friends I have who is a card-carrying hard-lefty liberal, we often end up talking about 'isms. Or I just tend to bring them up around him a lot. Anyways, most of the time he at least pays me enough lip service to make me think "well he's got it! a straight white guy who isn't a douche!" But then he'll say some COMPLETELY colorblind, sexist ridiculousness that just makes me want to scream. I've talked to him a lot about the role of an ally, and in no uncertain terms have said that I expect him to behave like one, that he shouldn't just assume that we're on the same page and that if he SAYS something offensive I will take it at face value rather than waiting for the punchline. He knows all this, and yet he still complains to me about how hard it will be for him (a white male with a master's degree) to find a job when I (a white female with a bachelor's) have been working a dead-end job for the past two years, sending out resumes and praying for a chance to get into the my field of choice. I realize that there is definitely privilege in both of these positions, but for some reason, he doesn't notice the inherent differences between them. It also fails to register that all the jobs open to him pay about $20,000 more per year than the jobs available to me. I could probably list several hundred more small advantages this guy has had over me that result in a higher probability for success and freedom in life than I will ever achieve, but my point here is to say that allies should be aware of this stuff, that I shouldn't have to remind him at every step of the way that he has a leg up on me and thusly, shouldn't complain to me about the trivial struggles he faces. It's completely insensitive and smacks of ignorance.

The worst part of all of this, is when I confront him with his un-allyish behavior, and he gets defensive. I really don't do it that often, although he may disagree, but I'm a firm believer in picking your battles. I am careful to distinguish between his words and actions, and try to specifically point out what I found problematic and why. I refrain at all costs from calling him, the individual, sexist/racist/adultist/etc. I try to remain calm, rational. Still, calling him out puts me in such a vulnerable position, I don't want to lose my ally, and I don't want to be misunderstood as perpetuating some killjoy femi-nazi stereotype.

The difficult part is, that he is still my friend. I DO want to be a good, supportive friend and "be there" for him. I want to be able to listen to his woes like he (usually) does mine and feel empathy for him. It makes me wonder if other people I'm an ally to feel this way about me; that if only I'd quit talking about how hard it is to be [insert privileged identity here] I'd be a decent friend to have around. I'm gonna keep trying with this guy, there's potential, and if I don't show him how to be a good ally, who will?