When I dated Cassie, she was a rough-and-tumble butch who was more masculine than feminine and that’s just the kind of woman she was: a muscular and freckled force of nature in ripped Levis and trashed Docs. She loved light beer and made a mean mixed tape. She managed the bar where I worked and was in turns fierce and delightfully funny. An impulsive protector, she once chased down a man who shoved me off the sidewalk on Haight Street. Like many stone butch women who enjoyed a fluid gender identity and tended towards masculinity, we called her “Cass,” avoiding gendered pronouns altogether.

Cass and I dated briefly after I got dumped by a crush that took me back again, and after some temporary awkwardness, Cass and I remained friends.

True to her big-hearted nature and physical strength, Cass eventually left the drink-slinging world to become a firefighter and pit pull rescuer.

When I moved from the Bay Area to Los Angeles, Cass and I spoke on the phone every six months or so, and I got an annual Christmas card with pictures of her latest adopted dogs in red felt Santa hats and elf costumes, accompanied by a personal update about her latest girlfriend or love interest —always straight girls or high femme ladies whose only gay partner was Cass.

The last card I received was a collage of Cass’s dogs and two cats who had died within a six-month period. Then, a couple of months ago, I received an email from Cass introducing herself by the name “Nathan.”

Nathan informed me that he had undergone top surgery and, in a good-humored tone stated that he looked forward to having “All male anatomy. No more female.” He mentioned in the email that he was sure I would not be surprised. (I wasn’t.) Of course, I was happy for Nathan and chipper in my response. I mentioned that I had planned a trip to the Bay and would love to catch up in person.

A few days later, I received a phone message from Nathan.

He said that it was a strange coincidence, but his surgery date for his phalloplasty had been set, and it happened to take place during the week I had planned to visit. He would be home laying low but would love it if I could stop by. It’s a serious procedure that many trans men don’t end up doing: the technique involves grafting the skin from the patient’s forearm or thigh to create a working penis and extending the urethra so the male can stand while peeing. To some trans men, this final step is important in order to be completely free of their lady bits and to finally have more permanent working boy junk. Many female-to-males consider it a final chapter to their sex reassignment surgery: It makes things as official as possible.

Nathan was the fourth butch woman I had dated who was now a man, and when I heard Nathan’s testosterone-laced voice, it hit me harder in the gut than I would imagine.

I was supposed to be elated for my friend. In fact, I’d spent my entire liberal undergraduate education studying the complexity of gender fluidity and sexism in our culture and others. I’d spent my entire adult life fighting for queer and women’s rights. I was supposed to raise my fist in the air and defend my butch ex’s journey to manhood, where he could shine and be the best version of himself possible.

That was how I wanted to feel, but actually, I felt a little sad—and then angry with myself for feeling that way. On some level, Nathan’s transition represented the loss of a woman I adored and respected in part because of the uniqueness of her femininity. As much as I wanted be supportive of a friend’s next step, I realized that there is also no blueprint for this strange new grief: the loss of all of my butch exes leaving the ranks of women to become men. It felt like a visceral betrayal, even though I know logically that it’s nothing of the sort.

I came of age in the 90s in San Francisco when butch-dyke hotties were many-splendored. Now, in many of their places are dudes with new names and lower voices and body parts. Gone are the women I dated who had the swagger and the piercings, the tough chicks I dated and fisted and loved. As queer butch hotties, they were my masculine lovers, turning the hetero-normative paradigm on its head. As trans men, they’ve ended some of that gender-fucking sisterhood.

I realize my butch exes very much want their bodies to match how they feel inside and may have felt inside their entire lives. They were given names like Cassandra and Rebecca. They grew up with enviable natural C cups and feminine curves, but those curves happen to be on the wrong body.

They wanted to fuck with their own dicks. I get that.

While I look forward to a new friendship with Nathan that’s grounded in shared memories and love, the fact remains: I treat dudes differently in ways that are hard to explain. I am not alone in this.

Vexed by my discomfort, I met with Danny, a friend who transitioned to male in 2007 and has undergone chest surgery but has kept his ovaries and uterus.

As a marathon runner, he realized that women treat him differently out on the running trails.

“I scare women now,” he said. He told me a story about jogging and passing as a man:

I was running around the reservoir in broad daylight and I started running behind a woman who was running a pace I wanted to run. She turned off the path. I chuckled. Because I was following her I said, “Oh, I was following you.”

She said, “Yes, I know,” and stopped abruptly. It was like getting kicked in the nuts. This reminded me of how I was seen in society: I scared her. It was a wakeup call.

Ironically, I am a way more kind, gentle person as a guy.

Before Danny made the difficult decision to start taking Testosterone, his biggest fear was that he would lose the intimacy of feminine bonds. When I asked what he meant he said, “As a man, I love more distantly.” He was the first trans man I had heard describe the loss of being feminine in a way that made perfect sense. He also grieved the loss of being welcomed into women-only spaces, like the Michigan Women’s Festival where he went for eight consecutive years. It’s more of a personal belief than an official festival policy: “If you make a decision to be a man, you shouldn’t be in women’s space,” Danny says.

After speaking with Danny and Nathan I realized that this new grief is a part of all of us now: the parents and partners of my trans friends and the spaces and circles they used to call home.

I may not have sleepovers with my trans men friends who used to be hard-core feminist dykes, but that doesn’t mean we have lost them entirely to a legion of men. Like a new set of boobs or a phalloplasty, this new grief is a part of our terrain now.

The less we silence our grief and the more willing we are to tell the truth about it without being accused of being unsupportive, the better chance we have of loving less distantly.

I have not yet changed Cass to Nathan in my phone because I’m not ready to do that yet. I may secretly keep Cass around until I get to know Nathan better and wait for the two to merge and adjust in my heart and mind. I have one month until I visit Nathan during his bottom surgery. One month to show up with my whole heart, supportive and a little bit sad and excited for him to embark on his journey to manhood.