Dear Charlie by Brett Dineen

Dear Charlie,

Some things never change.  After transferring to Tabor Academy to repeat of my freshman year, I felt like I had the same conversation with a thousand people at these annoying mandatory orientation activities.  Any Prep School kid knows exactly what I’m talking about.  The conversation would go something like this:

Me: “Hi, I’m Brett Dineen.  What’s your name?”

Stranger: “Hi Brett, I’m New Person. Nice to meet you.”

Me: “Oh cool nice to meet you, where are you from?”

Stranger: “Oh, I’m from wherever. How about you?”

Me: “ I’m from Marion, Massachusetts.”

Stranger: “Cool, play any sports?”

Me: “Yeah, I play hockey. How about you”

Stranger: “Nice, I play soccer. You have any siblings?

Me: “Yeah. Older sister, Meg, and younger sister, Elizabeth. How about you?”

My goodness I felt like I must have had that conversation with everyone three times.

Another unchanging part of my life was my identity as a hockey player.  I lived for the crunch of steel edges in the cold, hard ice.  The ring of a post was my favorite musical note.  And for that rush when you scored. Holy smokes, there was absolutely nothing like that.  It never got old to me.  Now, this may be due to the fact that I just flat out suck at scoring goals, so even at the ripe age of 20 there is still a sense of novelty to the thrill of lighting that lamp.

Sports ran deep in my family’s veins.  My father was an All-NESCAC defenseman his senior year as Mens’ Ice Hockey captain at Middlebury College and a standout baseball player as well.  My mother is still the all-time leading scorer and rebounder for Trinity College’s Womens’ Basketball program and was the ace for the softball team to boot.  Meg earned a quite impressive eleven varsity letters at Tabor and could have had twelve if she didn’t get sick of soccer her senior year.  Not a big deal.  If I’m not mistaken, we were bred to be NESCAC athletes.

Of all the sports we tried as kids though, nothing stuck like hockey.  We were skating by the time we could talk, and it was a typical “family day” if it was spent at the rink.  We were your typical rink rats.


There are some things that do change though.  As successful as Meg was as a high school athlete, she did not want to continue her athletic career in college and chose to pursue music at Middlebury College.  Elizabeth too was starting to distance herself from sports.  She had always loved hockey but she realized that it wasn’t for her at a young age, and so she took up swimming and was pretty damn good at that.  Elizabeth’s true passion, however, were the arts.  She was obsessed with all the fundamental art forms such as drawing, music, painting, and more.

Now for me, hockey was still my focus.  My goal was always to make it to the next level. Making the jump to prep hockey from public school was that next level.  Growing up watching Tabor Hockey play, I knew I had quite the challenge ahead of me, but I was determined.  While it was a close call, I made the team my freshman year and never looked back from there.  Walking into the locker room as a shrimpy 5’9”, 145-pound freshman and seeing the tree trunks that were Ryan Barnes’ legs made me realize that I had a lot of work to do to get up to speed.  I wasn’t playing with boys anymore.  These were men, and I was still a boy.  As challenging as it was at times, doing battle everyday against them forced me to become the best version of myself that I could possibly be and I gained a lot of confidence in my game that year.  It was at that point that I made it my primary goal to play college hockey as that was the next level.

Playing prep hockey, as almost any prep hockey player will tell you, was the time of my life.  My first three years flew by, and all of a sudden I was entering my senior year, in the heart of trying to find a home to play college hockey.


Entering my senior year was a little different than the previous three years, however, because my sister Elizabeth was now one of the many fresh faces that made up the freshman class.  Most people would tell you that going to school with your siblings is awesome and I’m not saying that isn’t true, but to be perfectly honest, I was nervous entering the year with Elizabeth being a freshman.  Although many senior boys have freshman sisters that they worry about for a multitude of reasons, my worries for Elizabeth were of a different variety.

Meg and I shared many similar traits growing up.  While I would never consider us big-time extroverts, being social and finding our crowd had never been much of an issue. The same could not be said for Elizabeth.

She never had many friends over the house and was always anxious about meeting new people.  A lot of girls go through a tomboy phase when they are young, but Elizabeth never really grew out of hers. She always had this manliness about her that other girls did not.  For one she was just huge, like one of the most jacked 14 year-old girl you have ever seen and had height that my Dad would have killed for in his playing days.  The girls’ crew coaches were drooling over the prospect of having her anchoring their first boat for four years even though she had never picked up an oar.  She also always loved the way she looked in baggy jeans and an adult medium hoodie.  It is safe to say that the first time I saw her in Tabor dress code I just flat out laughed because I couldn’t remember the last time I saw her in a skirt.  She looked as out of place as Dwight Schrute in a jewelry store.

How out of place she looked was what made me nervous about her arrival at Tabor.  I was nervous that she would never be able to find her group at Tabor because she was just different. Much to my delight, she proved me wrong initially.  She was sitting with people at every meal and I was happy for her to say the least.  It looked as though I would have nothing to worry about.

However, it is never that easy.  Just like any new toy, the novelty of people wear off with time. As Elizabeth got to know people better as time passed, she started to find more of the people she had initially considered friends were not truly her friends.  She had still not really found her crew while most of the freshman class had developed your typical high school cliques.  The number of people at her meal tables were steadily declining.  I realized that she often spent weekends at home as opposed to going to hang out with friends in dorms or the athletic center and soon started to isolate herself.  Me being my naïve teenage self, I really didn’t pay much attention to it.  She never voiced how she felt to me directly but in the back of my mind I knew she was struggling.  Looking back on it, would it really have been that hard for me to eat a meal with her, or play a game of pool with her in the athletic center?  Why didn’t I just have a conversation with her and ask her how she was really feeling?  Sometimes that is all it takes to turn the tides and get someone going on the right track.  It all came down to the fact that I was too focused on myself, my college process, and the upcoming season to worry about being a good brother.  That is inexcusable.

All it takes is one day for those things that you thought never change to actually change. That day came in the middle of last April.  For months, Elizabeth had been seeking help after admitting her depression to the family and seemed to be doing a little better.  She seemed to have found a new crew that included many upperclassmen, and while many of these kids were not necessarily people I considered my friends I was just happy to see her doing better and finding her new clan.  But I was completely taken aback one day when my parents approached me one night with a note that Elizabeth had left them before heading off for after-school activities.

I cannot remember exactly what this note said but its message was and still is loud and clear. For her whole life Elizabeth had felt trapped. Trapped inside her body.  She knew who she really was and it was not Elizabeth.  Elizabeth was Charlie and wanted to begin the transition to identify as a boy.  Charlie’s pronouns were to be he, him, and his, just like any other regular dude.  Charlie was excited to be coming forth with this and finally being able to live his life the way that most accurately reflects who he really is. However, he did not want this to become public yet.  This was only the way it would be at home, but at school everything would be the same.

I didn’t really know what to feel after I read the note.  I wasn’t angry and I wasn’t sad. Instead I just felt kind of lost, and this feeling lingered for weeks. I mean, when something that you are so sure of just disappears or changes you are simply shocked. Imagine just having your pet’s name and gender change all of a sudden and start calling him by a new name.  It’s hard to explain just how foreign it all was to me.  It’s like breaking a habit that you’ve had your whole life but multiplied by a hundred.  It was not an easy time for my family and I.  The world stopped for a few days in our eyes.

After over a week of going through the motions in the classroom and on the baseball diamond I knew I needed someone to talk to.  I needed to just vent in a sense and just explain to someone who would understand what I was feeling.  Typically in this situation I’d turn to my parents, but I knew they felt the exact same way as I did.  Next on my list would be my older sister, Meg, but she was currently traveling the world and also trying to adjust to this change.  The next person in my progression would have been a friend or teammate, but I wanted to respect Charlie’s wish to keep it private for the time being.  I needed someone who was educated in the LGBTQ realm and someone I could trust; I found that person in LuLu Ward.

Advice is not the point of this article but if I had any piece of advice for anybody, it is to find that friend that you could tell absolutely anything to because you just never may know when you need them most.  Find your LuLu Ward.


LuLu was a classmate of mine who I had always been close with throughout my time at Tabor. She was smart, progressive, and someone I had always been very comfortable speaking openly to.  We met up one night during study hall and boy did she get an earful from me for a good 30 minutes.  I lifted everything off of my chest there in Beebe Grill for her to absorb.  I really didn’t even need her to say anything to me, but she said just the thing that stuck with me the most over the next few months.  It went something like this:

“Listen Brett, I know that this is all hard to accept, but you need to look at this differently.  Your brother isn’t hurt and he’s not terminally ill.  He’s happy and he’s ready to become whom he has been suppressing the first fourteen years of his life.  Things could be much, much worse than this.  When you spend time with him, you will notice that things really aren’t that different between you too.”

It was the shot of reality I needed.  And it turns out LuLu was pretty spot on.  Charlie still binge watched The Office, challenged me to the occasional map of Star Wars Battlefront, and starred in every open mic night on weekends. Elizabeth had really just been Charlie for all those years after all.

Now, I realize that many people who read this will have differing viewpoints than I do on this matter.  I am not writing this piece to be political and I am not asking any readers to march in pride parades in your nearest city.  I am writing to tell the story of my family.  However, I do not think it is unreasonable for anybody, regardless of your political background, to respect the LGBTQ community and their way of life, and to treat them as you wish anyone would treat you. Call the members of the LGBTQ community by their desired names and use their desired pronouns.  It really doesn’t take much effort on your part.

Now, if I take some heat for this article, so be it. Family is family and I will always stand behind mine no matter what other people have to say about us.  At this moment in Charlie’s transition, our family cannot do some of the stuff we used to do together.  We can’t all go for a swim at the beach or dine at restaurants that aren’t accepting of the LGBTQ community, but that does not matter to me.  I’ll go for a swim on my own time and there are no Chick-Fil-A’s nearby anyways.  I’ll take everything exactly as it is now, with two loving parents, a kick-ass older sister, and a happy younger brother.


Now Charles, this one is for you, from me:

Dear Charlie,

It’s been quite the ride, but I am thankful for it and I know we are both better people because of it.  You are one tough son of a bitch.  I know we sucked at CCD and never got confirmed (hope our grandparents don’t see this), but I do believe that God gives his toughest soldiers, his toughest battles.  You are as tough as anyone I know in your own way.  Keep it up and keep fighting for what you believe in.  Even though we have our disagreements, that’s just a part of being brothers.  No matter what, I have your back, and I know you have mine because that’s what brothers are for. I am excited for what the future has in store for you.

Love you always, kid,


Upon my arrival at Middlebury College last fall to begin my freshman year, one of those things that I thought for sure would always stay the same, changed.  Introductions went something like:

Me: “Hi, I’m Brett Dineen.  What’s your name?”

Stranger: “Hi Brett, I’m New Person. Nice to meet you.”

Me: “Oh cool nice to meet you, where are you from?”

Stranger: “Oh, I’m from wherever. How about you?”

Me: “ I’m from Marion, Massachusetts.”

Stranger: “Cool, play any sports?”

Me: “Yeah, I play hockey. How about you”

Stranger: “Nice, I play soccer. You have any siblings?

Me: “Yeah. Older sister, Meg, and younger brother, Charlie. How about you?”


Edited by: Angelos Tsalafos (editor & publisher)




2 thoughts on “Dear Charlie by Brett Dineen

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