You guys, you aren't going to believe this one. Seriously, I can hardly believe it happened. In San Francisco. I was almost in tears, I was so upset.
I understand that Straight Dudes have a hard time with the fact that I've only dated women for 13 years, that I still very much identify as queer, and that I have a a transgender best friend. It's a lot for them to wrap their heads around. So, I try to be gentle. Ease them into it, bit by bit, and never on the first date. I have learned to try to say it as casually as possible, allow at most two questions about it, and then quickly change the subject. It's almost a fine art. But, sometimes, things don't go as planned. This was one of those times.
So, I'm on a date with this guy. It's our first time meeting, so it starts off a little awkward. We get coffee (separately. Apparently, he was waiting just outside of the coffee shop, where he could see in but I wouldn't immediately spot him. He waited until I sat down to approach me, saying he wanted to give me time to "get settled." I have a feeling he just wanted to make sure I was cute), and then wander around the book store next door. Within 10 minutes, he asks, as we pause in front of the pscyhology section, "So, what kind of books do you like to read? LGBT books?" and points to a copy of Gay Lives. I smiled and answered the question, pretending it was the joke he misguidedly meant it to be.
We wander out to the bay, and walk along this long pier. We're chatting, and he gets this bright idea that he should take a picture of the bridge. And then of me. And then ask this homeless guy to take a picture of us together. And then text it to his mother. Seriously, this happened. Did I mention this happened right after he was mentioning to me that the last time he was on the pier, he was so upset he was "wishing [he] could keep walking off the end"? It was over losing a temp job, but don't worry, kids, he got his life together.
We then walk back inside, and he starts telling me about finding Jesus (and that isn't a euphamism), and his life with the church. I mention I'm Jewish, and he starts grilling me about whether or not I believe Jesus is the Son of God. As I plan how to get out of this situation, I somehow find myself saying, slowly, "Well, I have to be honest, I'm queer, and most religions just aren't okay with that." "What does that mean?" he replies. "That I'm queer? Well, that I'm not straight." "So, you've dated women, or what?" "Yes, I've dated women."
I allow the requesite two questions. They're benign and earnest. I think I'm in the clear, and can go back to planning how to get out of a plain and simple awkward and boring date, when he says it:
"You know, I kissed a guy once. I was closing my eyes and trying to pretend he was a girl. He tried real hard, but even though she identified as a woman...well, he, I guess...he'll never be one. He's one of those trans..."
"She was transgender?"
"Yeah, I guess so. You know, I get it, that they feel in their mind and their heart and their soul that they're female, but they'll never be female."
I was livid. Seeing red. Tears stung my eyes as I tried to convince myself that flipping the table over on him was a bad move. He was 6'3", so I (probably) couldn't take him. Instead, I looked him dead in the eye, smiled, and said, "You know, actually, my best friend is transgender." He sputtered for a moment, and then asked me what it was that made him male, and then had the nerve to ask if that was an appropriate question. I told him it absolutely was not. He fell silent for a moment, and then the flood gates opened. He told me about his time in outpatient rehab (he was in for alcohol abuse, apparently) that he ended up at an LGBT treatment center, and THEY discriminated against HIM, so now of course he knows our plight. He told me about how the new guy at his church was "obviously" gay and no one wanted to be friends with him, but HE was the one who went out of his way to be friends. He told me about how his job sometimes has transgender individuals come in and he treats them the same as everyone else (except for the fact that they "can't just say that they identify that way, they have to prove it, you know, with medical documentation"). He told me how he was sooooo progressive that he even had gay roommates. GAY ROOMMATES, people! Of course, the gay roommates would make comments about him when he'd walk to the shower shirtless, and he told him he couldn't live like that, but let's not split hairs here.
Not long after this, he tried to hold my hand. I politely told him it was time for me to go, thanked him, and wandered off to BART.