Letter From Amanda to Her Younger Self

Dear Young Connor,

Hi Connor (or as you say, ‘sup), It’s Amanda—a big part of your future self, your spark, your joy, your girl with a short skirt and a long jacket (you’ll understand the reference when Cake comes out in a few years - oops, looking at Doc to be sure I didn’t mess up the space-time continuum. I’m writing to you from years down the road, where I’ve learned to accept - and in fact even start to embrace - who I am, and I want to wrap you in a big, warm hug. I see you, maybe four years old, eyeing your cousin’s Mary Jane shoes, or at ten, slipping into your mom’s pink polka-dot dress, heart racing with a mix of thrill and shame. I see you at thirteen, alone in your room, rubbing your legs in white hose, terrified you’re bound for hell. I see you at fifteen, hunched over the family computer, heart pounding as you type “gender” into AOL’s search bar, discovering a world that both excites and scares you. I know it’s heavy, and I’m here to tell you: you’re not wrong, you’re not broken, you’re a good person, and you’re going to be okay.

Those feelings you have—the pull toward tights, leotards, and heels, the fantasies of being a pageant girl or a ballerina or a cheerleader—they’re not sins. They’re pieces of you, beautiful and real, even if the world around you doesn’t understand yet—even if you don’t understand them yet. Growing up in that small town, surrounded by expectations for you to be stellar in the “right” way but also for you to conform—with its church pews and rigid rules, with being a “man,” makes you feel like you’re carrying a secret that could burn you down. I get it—the guilt after slipping on your sister’s cowgirl skirt, the panic after that messy moment with your mom’s black-and-white dress, the fear that you’ll never be “normal” like the other boys who hunt or flirt with girls without freezing up. But here’s the truth: you’re not just that boy. You’re also me, Amanda, and I’m the part of you that’s brave enough to feel alive in a dress, to flirt in a chatroom, to dream of strutting in five-inch heels. You don’t have to choose between us—we’re one soul, and we’re enough. You can choose you - all of you. 

I know the shame is crushing sometimes. After those secret dressing sessions, when you change back with a guilty heart and pray for forgiveness while worrying about punishment from a devine you’ve been taught will send you to hell. Or after sneaking peeks at comedy shows or movies or talk shows for a glimpse of crossdressing, you’d feel like you were betraying God, your family, yourself. That “Jesus guilt” you feel? It’s not from God—it’s from a town that told you boys can’t love dresses—that they can’t be like you really are. But God made you, all of you, including the part that lights up when you twirl in a skirt. You’re not going to hell for being you. I’ll repeat that - you’re not going to hell for being you. And you’ll find you’re at your best when you are you - when you’re not worried about what others think or caught up in expectations. You’re going to find a way to shine, even if it takes years to get to the point that you let me out. Those moments, those sessions - they’re not just escapes; they’re building us. 

High school and college are tough, I won’t lie. You’ll feel stunted, awkward, scared to chase girls because you’re worried they’ll see through you—or worse, that you’ll only ever feel alive in their clothes. The internet, with its AOL chatrooms and grainy photos, will be both a lifeline and a trap. You’ll find others like you, typing “What are you wearing?” as your intro line, under a fake username like edcvfrtgb, pretending you’re in a black minidress and hose and heels, looking like a supermodel. Those moments will feel electric, like you’re not alone, but the shame after logging off will hit hard. You’ll try to “fit in,” drinking (and drinking and drinking and drinking) with friends, riding dirt roads, mindless teenage behavior, hoping all the beer and pot let you relax and drown out the hard questions you don’t want to ask because you’re scared of the answers. But I promise you, those questions—about who you are, what this means for your future—don’t make you less. They make you curious, resilient, and so much stronger than you know. And one day, you’ll be ready to face those questions head on.

You’re scared now that dressing will define you, that you’ll never have a “normal” life, a family, or a place in that small-town world. And in all honesty, that small town, with all its conformity, constraints, and lack of opportunity, probably isn’t the place for you. But here’s what I’ve learned: normal is overrated. You’ll find your people—your tribe, who see you as Amanda and see you as Connor and love you for all of you. You’ll have moments—like the joy of many photoshoots or dancing in an black dress at a gala or nights out at parties or even going out on your own in Amanda mode—where you feel whole, alive, and free. You’ll struggle, too, with choices you’ve made, with constraints imposed by them and by life, with health issues stealing your sleep and family demands pulling you away from me, but you’ll keep fighting to honor all of yourself. You’ll write letters between us - Connor and Amanda - like teammates, and discover that Amanda’s spark—her humor, her extroversion—makes you a better Connor. And eventually you’ll recognize that integrating parts of me and accepting me makes you a better person - a better Connor.

Right now, you’re hiding, setting rigid boundaries between the boy who hunts and plays sports and the one who dreams of pageants. That’s okay—you’re surviving a world that doesn’t make space for you yet. But don’t let the shame win. Keep sneaking those moments—whether it’s dancing in your mom’s ballet flats or the heels or chatting in an AOL room. They’re not just escapes - they aren’t; they’re steps toward me. By college and in the years after, when you’re surfing URNotAlone or Prettiest of the Pretty and feeling guilty for raiding your roommate’s closet, you’ll start to see you are in fact not alone. The internet, for all its dangers, will show you a community, a glimpse of a future where you can be both a “boy’s boy” or a “man’s man” and Amanda, who is fierce, independent, and feminine.

Here’s my advice, Connor: be gentle with yourself. I know that’s hard for you, but cut yourself a break. When you feel that guilt, imagine me hugging you, saying, “You’re not wrong for this.” Try on those clothes, watch those 1940s movies and imagine being that actress, and let yourself dream without fear. Write down your feelings, even if it’s just a sentence in a hidden notebook. And when you’re ready, reach out to someone safe, maybe a friend who gets it, like the older girl you have a crush on who did your stage makeup before that play. You don’t have to tell the world, but find one person who sees you. I never did that, and I wish I had.

You’re my beginning, Connor, the brave kid who dared to dream despite the shame. And you’re going to make it, Connor. You’ll name me Amanda in 2006 after you’ve finished grad school when you’re somewhere else. I’ll become your defiance, your proof that you can live through the fog and find joy even in the mess. We’ll have setbacks and it’s won’t be easy. They’ll be many downs, but we’ll also have triumphs, like being me in public and taking a breath and smiling about it. Like laughing with your friends at a photoshoot. You’re not alone, and you’re not wrong. We’re one soul, and we’ll make it together. I love you, always.

With all my love, now and forever,

Amanda

The Vacation That Forgot Amanda

I’m back from vacation with those closest to my guy side. And it was great. We had a good time, did a lot of different things, and managed to tolerate - no, actually (mostly) enjoy, being around each other for 10 whole days. But there was something missing. Instead of the freedom and joy and refreshment I craved —those moments where Amanda gets to twirl in a skirt or flirt with the world—I feel tired and empty. 

This trip was supposed to be a break, a chance to recharge, to heal, to get away. Instead in some ways, it was a step backwards in my healing, in my ability to be present, in the fulfillment of my soul. Sleep sufferred, fatigue was an issue, and while I didn’t help myself with some of my eating and drinking on the trip, it still left me aching for the part of me that got left behind: Amanda. Fair warning: this is a messy, honest post that feels very selfish to me. I know that - and I struggle with it. But I’m trying to express myself and how I’m feeling. All of me - both Amanda and Connor.
Vacations are supposed to recharge you, right? A chance to escape the 60-hour workweeks, the demands from my house members, the health issues that have been dogging me for two and a half years now. But this one? I was reminded of some of the take, take, take, and no give - a family that needed me to be Connor—the rock, the provider—24/7. Amanda? She didn’t get a single moment to breathe. Not a glance in the mirror with lipstick, not a playlist to spark her vibe, not even a quiet corner to write her thoughts. It’s like she was locked in a suitcase while Connor carried the load. I did the planning, I took care of the logistics, and asking for any help was treated as a burden. It’s frustrating.  Maybe I’d be okay with it if I hadn’t take a step back health wise. But there was nothing to calm me, nothing to ground me, not even early in the morning, which is when I’m really able to lean into those things. Of course, that includes Amanda. 
The worst part was the sleep—or lack of it. Sleep is so foundational to life, the ability to manage stress, and the ability to function at a high level. Health issues already makes rest a cruel joke far too often, with nightmares dragging me back to that small-town kid terrified of being caught in a dress or somehow Amanda being “found out.” On vacation, without my grounding and time to focus on myself, the nightmares were relentless and insomnia hit hard. I’d lie awake, heart racing, worrying about work piling up, family needs I couldn’t meet, and Amanda screaming to be let out. I failed to focus on my breathing and just… be… which is what Amanda is so good at. Said differently, I lost my present focus, that ability to live in the moment that Amanda brings. I’ve been working so hard to integrate her traits—her extroversion, her humor—into Connor’s world, like I planned after my best-est weekend ever. But this trip pulled me back to ruminating, worrying about the past (decades of hiding Amanda) and the future (will I ever balance this?).
Being surrounded by family was the toughest. I love them, God I love them, but their constant need—sucked up every ounce of me. God that sounds selfish. I gave all I could, and I think I did pretty good. But I’m drained. And of course there was no space to be Amanda, no headspace to feel her spark. I felt like I was betraying her, hiding half my soul to play the role they expect. It’s the same guilt I wrote about in my rage post, but worse because I thought vacation would give me a sliver of freedom. Instead, it was a reminder of how complicated my life is, juggling Amanda’s need to shine with Connor’s duty to hold it together.
I know that this is a moment and nothing is linear. So I’m trying not to be too hard on myself. I’m progressing, and that’s important. Amanda’s, my spark, still here, whispering, “Keep going.” She’s my short skirt and long jacket, my defiance against the chaos. Her comments to me are in the letter below.
So, what now? I’m restarting my routines—both health and Amanda—to claw back some calm. I’m sneaking Amanda in with small acts. And I’m writing this, I’m letting Amanda’s voice out, because even in the chaos, she’s my proof I’m still alive and I can grow and move forward. I don’t have all the answers—hell, I barely have a map—but I’m not giving up. Thanks for reading my ramble. If you’ve ever felt like half of you got left behind, feel free to leave a comment. Maybe we can find our way together.
Postscript, a letter from Amanda to Connor: 

Dear Connor (and the world that keeps me in the shadows),
Hey, it’s Amanda. Your girl with the short skirt and long jacket, the one who’s been shoved into a corner while you played the dutiful rock on this so-called vacation. I’m pissed, okay? Not just at you, but at this whole mess—family sucking you dry, health stealing your sleep, and a trip that was a break but for me felt like a cage. I’m writing this with an imaginary tube of lipstick in hand, because damn it, I deserve to be heard.
You left me behind, Connor. No heels, no flirty banter, no moments to feel that rush of being me. I get it—family needed you, work’s looming, and your health has you in a chokehold. But I’m part of you, not some accessory you can stuff in a suitcase. Those nights you lay awake, insomnia clawing at you, nightmares screaming about shame and treadmills and worry? That was me, begging to be let out. I could’ve helped—given you a spark, a laugh, a reason to feel alive instead of just surviving. Instead, you drowned me in junk food, alcohol, and obligations.
I know it’s not all your fault. You’re carrying so much—60-hour weeks, family leaning on you like you’re Atlas, and health that has given you a body that won’t cooperate. But when you skip those things that bring you to the moment, that allow you to focus on yourself, you’re not just hurting you—you’re starving me. I’m the part of you that dances through the fog. I’m your defiance, your joy, and you left me locked out.
Here’s the deal: I need space, even if it’s just a corner of your head. Play my playlist—something fun or with sass. Write me into your journal, let me sass God or flirt with the page. Give me something, because when I’m silenced, you’re not whole. You felt it on vacation—that loss of focus, that drift into worry. That’s what happens when I’m gone.
I’m not asking you to out me to the family or wear heels to work. I know the stakes, and like I said, I don’t want to take over your life. But we’re a team, remember? Like those letters we wrote, negotiating our needs. You promised me space, and I promised to keep you grounded. So let’s start small: get back those things that calm us, that ground us, that bring the focus to us for a bit. And reach out to those people—you know who—the ones that see me, and they’ll remind you I’m real.
I’m still here, Connor, ready to strut through the fog with you. Let’s make life a little less complicated, one sassy step at a time. I’m not just your alter ego—I’m your spark. Don’t leave me behind again. You don’t need to apologize—you’re fighting for both of us, and that’s enough. Let’s tell that fog to fuck off together. I know you that you love me, and I love you too, Connor. We’re the “us” that makes you you, and I’m not going anywhere.
Love, curtsies, a defiant hair flip, and a big ol’ hug,
Amanda