May as well start with prison tutoring.

On the one hand, you're a piece of meat. I mean, you know that when you sign up for it, if you're female and young, you're signing up for getting stared at. In the world outside the prison, people noticing you follows several stages, starting at indifference and moving up through perception to interest and sometimes on to staring and talking and in very rare cases to whistling or lewd comments. In prison, the first few stages are either cut out or there's some special supplement they put in the food that gives the inmates the magical power to go from zero to sixty in under a second and run through indifference, perception, and interest in the time it takes me to register their presence in the hallway or the classroom.
Staring is the norm, as was made abundantly clear to me on my first day, when the education director took Fellow Tutor A and I on a tour of our classrooms and every head in the place snapped in our direction when she opened the door to let us meet the teachers. "They're young and they're horny," she told us with a fairly thick Jersey accent (she's awesome), "and if the wall were a woman they would stare at that."
It wasn't as if I wasn't expecting all of this. I may not have watched Oz (and I don't plan to until I'm done with this gig), but I know about prison logistics and I know about guys in their late teens and early twenties and I'm not an idiot.
Even when it was fairly obvious to me on that first day of orientation that there were guys in the corner whispering about Fellow Tutor A and I in Spanish, I didn't mind that much. In the real world, I wouldn't put up with that kind of thing, but prison, I told myself (and I still believe) is an already imperfect system and you have to take it as it comes and choose your battles wisely.
The battle I eventually chose was the Great Definitions Battle of April 2010.
Most of the time I spent tutoring, I tutored math. The teacher likes math, the inmates like math, and even though I usually hate it more than any other subject (except maybe chemistry--and that only because I'm counting physics as glorified math), I found myself liking math too because it's easier to teach students who like a subject than students who are barely putting in the effort. Grammar, I found, was not a fun subject to teach, and if I thought about it in terms of French I could definitely identify. How do you tell people who have been communicating perfectly well for over fifteen years that they're doing it wrong? Obviously as an English major I want people to be able to use the English language in ways that highlight its beauty and complexity, but that's in the real world.
But, then again, these classes are all about the real world. One of the subjects the teacher spent time on was Career Education, after all, and Career Education is focused on what the students could possibly do once they've been released. The grammar and the math (as much as it pains me to say it), those are for the real world too, as well as for their advancement within the prison school system.
So grammar is complicated. It's hard for the prisoners and it's hard for me to reconcile my sympathy for them with my love of the language, with my separation of the prison system from the real world, with my growing realization that teaching prisoners is more important, more of a last-ditch attempt, than teaching almost any other group of people in the country.
But I digress. Back to the Great Definitions Battle of April 2010.
I had determined that math was easy to teach, but I was still excited when they started doing spelling. Vocab! That was something I had always been interested in. So I sat expectantly in my corner, waiting for someone to break the ice and raise his hand and ask for help. Pretty soon, the guy sitting closest to me looked up from his dictionary and said, "I don't get this."
Spelling is really great, from a tutor's point of view, because the students are asked to use sixteen words in a sentence and sometimes they don't understand the definitions, and that's where you come in. So I slid over expectantly.
He passed me the dictionary and pointed to the word "boycott." The definition was pretty convoluted, so I said, "Okay, boycott. Well, it's like the bus boycotts during the Civil Rights Movement. When people stopped riding the bus."
He stared at me like I had a hole in my head.
Until then, my tutoring had taken the form of helping them get through the worksheet, making sure they understood enough to do well in the class. When this guy made it clear to me that he didn't know about the bus boycotts, I launched into a whole, wholly unrelated to spelling, explanation. (During this explanation, I found myself hovering over whether to say "black" or "African American" in this context, to...an African American man, but that's another story, for another very long post.) I didn't care whether he knew how to spell boycott or not, I just wanted him to know what a boycott was and why it was important to the history of the country.
This was my last day of tutoring for the semester, and until that moment I hadn't hit my stride. Listening to Roommate J talking about her experiences tutoring, I was sure I was doing something wrong, not making enough of an effort to get to know my students (although I had at least ten more than her, so that wasn't a very logical worry), not circulating enough, something. Explaining boycott, though, I knew I was doing something right. The student was listening, nodding, understanding what the word meant. And I wasn't shy (something I spend enough time fighting in the outside world), or nervous, or unsure I was being taken seriously. I chose the right battle and there I was, discovering the right tone to take as a tutor for inmates. Until then, I wasn't sure I would tutor again the following semester. Now I know that I will.

I'm still a piece of meat, though, even in my regulation, over-sized, bright yellow volunteer t-shirt.
The guy I explained "boycott" to was the guy who had complimented me on my shoes the week before--"Nice chucks."--and who was a frequent starer. Yes, I picked my battles, and yes, I said the staring didn't really phase me at first. After a while, though, it began to. Roommate J, when I mentioned this to her, didn't feel the same way, hadn't had the same experiences. I didn't object to being viewed sexually per se--that, like I said, I had totally expected and accepted--but it began to wear on me, week after week, to be seen as just one thing: just what I look like, that hot chick who comes in Monday mornings and helps out in Ms. T's room and sometimes scoots over close to help with math problems (oh, and she has nice chucks), and all the assumptions that come with it. It feels like you're being taken advantage of, and that's never good.
I guess it's appropriate that I was in prison when I came to the conclusion that the most dispiriting, horrible feeling is being looked at like you're not a person. This happens to prisoners all the time, after all, both in prison and in "the real world."
So it's a learning experience. Duh. That's why everyone's there. Fellow Tutor A might be there purely out of the goodness of her heart (she's that kind of person), but I'm there because I wanted to learn more, and lend a hand while I was at it.

Both those goals have been met, in ways I couldn't possibly have predicted in January, and this time next year I'll probably know even more about life, inside and out.