Wednesday, April 3, 2024

Missy's Prom

By Missy

Greetings! As a visitor to Stana's site and some of the blogs on her list (especially Kandi's Land) for a while, I finally felt comfortable enough to share a story from this past year. Thank you in advance for taking the time to read it.

Here's my brief introduction:

I have been fortunate for the past couple of decades to teach at a school that supports me. Beyond the classroom, my work includes coaching, advising, committee work, etc., but I have also tried to always be an advocate for students simply being themselves. I don't need to tell you how difficult that is for people of any age... but I believe teenagers need extra support when we can give it. My oldest daughter came out to my wife and me while they were at college a number of years ago and recently let us know that they are non-binary. That experience has given my work as an educator even more meaning.

The reason for sharing this small episode through Stana's site is simply out of "sisterhood." We are both educators and I appreciate her efforts. And... I just figured it was worth the effort to connect and share with somebody beyond my own circle – something which Stana clearly supports on her blog.

I have crossdressed for as long as I can remember. In the instance of how much time it would take to give the entire background, I will skip over my full history. But like most of us, I have had highs and lows and there have been numerous internal debates and battles with boundaries as I have worked to learn more about myself and find my comfort zone. Let's leave it at that.

With so much LGBTQ+ news getting both positive and negative attention in the media, I decided to be a part of the conversation in my school community by throwing caution to the wind last year. Over the past year and a half, I took the opportunity to be more fully myself in public and join students for their various "themed" days and events at school. This opened the door for some really fun "costumey" opportunities like Britney Spears, Mother Goose, Wednesday Addams, Taylor Swift, Barbie.

I am pleased to report that in addition to quite a few turned heads and subsequent discussion, there was almost complete support from both my colleagues and (more importantly, perhaps) my students. Or at least there were no actual difficulties... and there were some good conversations. And as I'm sure you all know, there was also a personal "freeing" factor that came along with these opportunities. Given the nature of many schools around the country, I continue to feel extremely fortunate to be in such an open and accepting community.

But... those are just costumes, right? Part of the ongoing struggle is trying to determine what "feels right" and how much of one's self can be shown on a daily basis. And so, as prom season 2023 neared, I pondered and internalized deeply and came to an important decision. That is actually the story to which I was initially referring, by the way... but I figured at least some setup was necessary, so thanks for playing along.

The 2023 prom story is told below via the email exchange between me (in red) and my Head of School (in blue). Very little of the original back-and-forth has been altered... only some names and school references. Here goes:

Hi Chief.

Heck of a year. I'm pretty much ready to wrap it up with a bow.

Before that happens, of course, are the festivities – my favorite of which is prom. A lot of my colleagues call me nuts to chaperone the event every year, but I love the atmosphere... I love the free-spirited joy, I love sharing the laughter, the smiles, the music (most of the music, anyway), the pageantry and I simply love being with students outside of the classroom. Plus, I was granted a "lifetime prom chaperoning pass" upon stepping down as a Dean a few years ago, so I might as well use it, right?

So... here's the thing.

I've been thinking about it on and off and then on and off and on again, but there was a strong resonance over the past week or so, which you echoed in our recent text exchange. I wholly believe in my own advice that I promote to students. Be yourself. Our school has, for the most part, allowed me to unabashedly be myself. I'm pretty sure you have enough evidence of my efforts to that effect.

As I have shared with you, my oldest daughter often had a bit of a hard time being her best self during her time at our school because of the somewhat homophobic corners of the community. She is beyond that now and knows and loves herself much better, but as a colleague reminded us recently there are lots of students who need support, safety, kindness, and role models on their journey to being themselves.

So therein lies the purpose of this email. It's in my nature to "ask for permission rather than for forgiveness," as the saying goes. Honoring the promise I made to my daughter (which I mentioned at the end of the Day of Silence this year) to try to be a better advocate for our LGBTQ+ students... but in all honesty, to also be true to myself, something like this photo (right) is my plan for prom, because... well, it's a part of me I embrace and have fun with, and which I feel our community has also embraced.

In theory, this shouldn't be any big deal, right? In fact, I'm hoping it doesn't even come across as "asking permission," but rather just a heads up... and the chaperoning will simply go on as usual without anything being out of the ordinary. Odds are strong that there will be a wide array of student fashion choices anyway, that run the gamut with regards to how many of them will present themselves, so should engaging with students in this manner really be of any concern?

I don't want to be phony and I would rather we not seem hypocritical with what we strive for with our students through our mission statement. I see this as a total "putting my money where my mouth is" opportunity and to paraphrase a recent student's presentation, I don't mind being vulnerable because that's how all of us will learn and grow.

To be clear, I'm not looking to take anything away from students; I'm not looking for self-attention and this isn't a "coming out party" by any means. I simply want to share the night and some memories with the students, but it's also a chance to remind those that need support that I (and we) see and hear them, and that we "get it." But... I think it will be fun, too, in the spirit of "you be you."

I also don't see this as "my prom" so I'm not planning anything over the top, but rather just dressing for the occasion as any chaperone would do for such an event. The few opportunities earlier this year during which I dared to be myself were received very positively by the community (from what I could tell) and supported, especially by the students and colleagues who bothered to say something and a few parents who went out of their way to let me know that they appreciated my efforts on behalf of their children. That meant a lot to me. At least there was no backlash of which I was aware, but one never knows what goes on behind the scenes. Thus, I am hoping that this would be just more of the same.

If, however, you do not feel that the time or place is appropriate for whatever reason, I will respect and stand by that decision because this is a want, not a need, that I think has the potential to help our community, especially during Pride Month.

Whew. That wasn't easy to write (and I didn't know if I was ever going to hit send), but I had to do it and I feel good having verbalized it. I appreciate you reading an email of this magnitude, and as always, I appreciate your support in my daily workings at school.

Please let me know your thoughts, so I can plan accordingly. Thank you.

Hi _______.

This is easy – sure!

Thanks for checking (which I view more as a sounding board that comrades rely on one another for – to “check our own weather report,” if you will). Thanks also for the openness and candor. I’m honored.

You embody our mission, core values, and mottos through your actions every day. And while your craftsmanship as a master teacher is inarguable, it’s your authenticity and the joy you bring to school that allows you to build such great partnerships with kids, colleagues and families. Prom is meant to be a joyful, fun celebration and I love the idea of you embracing and having fun with it.

As TB12 would say, “Let’s GO!”

Thanks Chief.

I appreciate the quick response and your kind and affirming words… and your accepting forecast of my “weather report.” [:-)]

Let’s GO, indeed.

Hope you enjoy the rest of your weekend.

And that was that, dear readers.

Once it was cleared with the powers that be, on the afternoon of prom, I let all three of my children know what I would be doing, via this note, accompanied by that email exchange with our Head of School.

Hi kiddos.

When you have the chance, please read the thread of the conversation between me and ____ from a few days ago.

Tonight I'm going to be a little brave, a little vulnerable and have a lot of fun (I hope) and hopefully, do a small thing to help out an important part of our community.

I just wanted you to hear it from me first so there's no mix in the message... and hopefully you simply "get it." Meh, might not even come as a surprise to you. [:-)]

Thanks for reading. Love you a bunch.


They were wholeheartedly cool with the idea as was my wife (she has learned along with me for the past 30 years). I am blessed with children that understand the need to be supportive of others, empathetic and as open as possible.

Two of my children are starting their careers as educators this year and I like to think that this was just another lesson for them.

Oh, the Prom itself? 100% Amazing (photo right)

I won't lie. I have dreamed of being fully dressed for an event like that for a long time, so I went all out and loved the result. And as has been the case, my colleagues were fantastic and most of my students embraced my choice... or at least were tolerant, which was a minimal expectation.

A few students obviously wanted a photo or two, and many asked why I was dressed as I was. Thus, I got to talk a bit about my daughter and their struggles while at school and how I was choosing to use one of my "superpowers" to hopefully raise awareness of the difficulties that come along with personal gender journeys, the need to pay attention to mental health, and again... the importance of simply trying to be yourself.

But I'm also pretty sure many of them knew that it was an indescribable night for me, too. Now well into my 50's, I think about the "you only spend time on this big blue and green ball once, so make the most of it while you can" mindset more than ever.

So that's the story I have wanted to share with a wider audience for a while. I still try to keep some things somewhat private, but sending this note to Stana was potentially therapeutic. I have also been thinking about Prom 2024 for a while, so... we'll see how that plays out.

Thank you again for taking time to read part of my evolving story. 


Source: Rue La La
Wearing Michael Kors

Kevin Kline femulating in the 1998 film Wild Wild West


  1. Thanks Missy for sharing your story and for being there for your daughter and your students. I’m glad you had that opportunity and that your school allowed it. It does send an accepting message. I am also glad that you can use Stana’s site to share your story with even more of us.

  2. Thank you for sharing such an amazing and positive story. Given some of the -ahem- 'news' going around at the mo, to read about acceptance and kindness is fantastic. Thank you!

  3. Missy,,,,thank you so much for your honesty and for sharing your story,,I wish I had had a teacher so caring in my life,,,thank you again! Trina

  4. On my! First of all Missy, I am honored to have been mentioned. Now I have to wipe away the tears. One of the things that brings me such pleasure is for sisters to have the same types of experiences that I have been blessed to have. Bless you and thanks to our fairy Godmother, Stana, for spinning the tale!

  5. As another contributor to Kandi's, I can only say well done too! Congratulations on putting yourself out there--taking the risk, and reaping the rewards.

    I am 1000% sure now that you have broken the ice you are planning your outfit for the next prom!

  6. In my opinion clothing needs to be decoupled from a person's gender. I read somewhere men's and women's clothing did not strongly diverge until around the 1500's. As I have remarked before I wear dresses far more frequently than trousers, and yet I regard myself a man and not a trans-woman.

    Having said the above I applaud Missy for having the courage to dress as a woman and being given permission to do so.


  7. Also as another contributor to Kandi's land I want to congratulate you on first taking those risks throughout the school year and having these risks cumulate for your prom attire. Very well done.

  8. Missy, thank you so much for sharing. It was exciting, uplifting and empowering all in one message.

  9. Missy, I apologize in advance and don't mean to offend but I am going to be a little contrary here to the other comments. I can appreciate your desire to express your true self and educate others about your transgender status but prom night is a very special night for students especially the girls. The focus should be on them and I think presenting as your female side at such a big event in the students' lives took some of that focus away from them in spite of what your best intentions were.

  10. It's a tough call as to whether Missy would be a distraction on prom night. I went to an all-male city-wide high school. There was no prom night. Over the years my wife and I happened upon high school kids congregating at the local mall to struct their stuff. What happens now, if the kid and a prom date are a boy-boy couple or girl-girl couple. And, in a case I know a high school trans-girl showing up in a floor length evening gown? Maybe, Missy presenting at the prom in a good thing because there were plenty of boys and girls not presenting in their "true shelf" because of the pressure of societal norms and expectations. I am happy that Missy's school administration was supportive. Of course, the supportive was not universally supportive. In the case I am aware of, one of my friend's (now deceased) grandchild came out as a trans-girl during high school. Her treatment and non-support by the school administrative was brutal. At a minimum Missy's attendance would have shown to some boys and girls that they are not alone. Maybe one or two boys and girls would go on to live an authentic life rather than hiding and struggling.