When my brother graduated from college, I was just finishing my freshman year at Northwestern. With one or two exceptions, I was closeted to most of my college friends. (Or is it “closeted with?” ACT tutoring is messing with my head. What’s the proper idiom?) My first major negative experience with a therapist – the one who told me I “probably wasn’t trans” – had scared me away from seeking medical or therapeutic help in figuring out my trans identity. I was still figuring a lot of things out, something which is probably true for most college freshmen.

A moment of my visit to my brother’s graduation sticks out in memory, and still occasionally gets me ribbed by family members. We were at a restaurant in town, my family and I, celebrating my brother’s impending  graduation. People were ordering drinks, and someone (probably my dad) made it clear I could have an alcoholic drink, too, should I so desire. So while everyone around me ordered beer or wine, I ordered a rum and coke.

Looking back, the reason I did it (and the reason my family finds it funny) is because I didn’t understand that there was a difference between beer or wine and mixed drinks. So while I probably could have ordered beer or wine without incident, ordering a rum and coke was cause for conversation.

Remembering all this still makes me a little embarrassed, because I hate not knowing how to behave. A big part of my transition has involved figuring out how to behave, how to present, how to interact, how to identify. And a big part of my hesitation around transitioning stemmed from not wanting to feel like I didn’t know what I was doing, didn’t know how to do something, not wanting to feel like I didn’t understand.

Part of growing up – and part of transitioning – is learning how to do things you don’t know how to do. And no one likes being embarrassed or feeling foolish; I don’t exactly have a monopoly on that experience. Another time, in high school, the pride youth group I attended had been listening to Melissa Etheridge, and in particular to Scarecrow, a song about Matthew Shepard. I was out to my parents at that point, but not to my brother. On a family shopping trip, I bought Breakdown (the album with Scarecrow) at a Best Buy. On the ride home, I asked if I could play it in my dad’s fancy new in-car CD player. We drove in awkward silence as Etheridge sang out the pain and anguish of being alone and different. And, in the back seat, I felt alone and different than these strangers, my family.

I want to write something in defense of awkwardness. In defense of putting yourself in a situation where there’s the potential for embarrassment or discomfort. I wouldn’t have been able to transition had I never stuck my neck out, been willing to be uncomfortable, been willing to be unsure. No one could ever grow up at all if they stayed perfectly safe and sequestered. And one of my big life lessons over the last few years has been, “People care less than you think they will.” To put it another way, everyone is tied up in their own shit and doesn’t have time for yours.

It feels somewhat silly for me to say that awkwardness still holds such fear for me. I’ve performed in front of large audiences, taught classes with kids and adults, spoken at great length about very personal issues. I’ve been topless on stage in front of both of my parents, and their significant others. It seems like I should be pretty awkward-proof.

And maybe faking awkward-proof-ness is really all it takes. How should confidence be defined? Is real confidence believing that you’re confident, or being perceived as confident? There’s a parallel with gender, there… And I know I can fake confidence, but I don’t like to that I’m  ’faking’ gender, whatever that would mean.

Maybe I need to embrace the awkward. The not-knowing. The willingness to say “I’m not sure how this will work out.”

But it sure is fucking scary.