A young man battles his own anxiety before asking out the girl of his dreams. Should he go as “himself”, or should he don the armor that gives him strength and confidence? Which will she accept? And more importantly, which is truly him?

Ryder Bateman stares at his thin, wiry and generally unimpressive nude body in the bathroom mirror of his college dorm, pondering a single question: what to wear?

Over the past few months, this question has been growing especially hard to answer, but today it feels nearly impossible, and the anxiety that grows over the impending decision sits like a ball in his throat. Ryder turns on the faucet for the cold water at the bathroom sink and splashes his face. The chill sends a shock down his spine but does nothing to quell his growing anxiety. So, with shaky hands, he cups his fingers together while letting the cold water collect in his palm. He tries to bring the water to his mouth, but with all his shaking, there’s barely anything left once his hand reaches his lips.

“Shit.” Ryder curses under his breath. He takes hold of his right wrist in an attempt to steady himself. The lump in his throat feels like it’s doubled in size. He feels like he wants to vomit, but forces himself to swallow down the feeling. This is no time to be getting sick. More determined now, he uses both hands to cup the water pouring from the faucet, leans in, and slurps up as much water as he can handle. The cold seems to bring some sense of relief but the shaking still won’t stop.

“What the hell do I wear?”

Although he keeps posing this question, Ryder’s true dilemma is not that he does not know what to wear, but rather, whether or not he should put on what he wants to wear. It’s such an important day – he needs the confidence that his armor gives him. Without it, Ryder knows he won’t have the nerve to do what he has to do. To talk. To really talk to her – before it’s too late.


Just the thought of her makes Ryder’s skin prickle in excitement. Like most guys, the first thing he noticed about her was her looks. Big expressive brown eyes, a head full of wavy chestnut brown hair, and long legs that just seemed to go on forever – she is unbelievably gorgeous. In fact, she’s an Instagram model with a fairly large following. Alyssa turns heads everywhere she goes. But it’s not just her looks that draws people to her. Alyssa is also probably one of the nicest, most down to earth people Ryder’s ever met.

For a long time, Ryder didn’t realize that Alyssa knew his roommate, Conor, so imagine his surprise when he saw the two of them hanging out in his dorm a few months back. Conor had been so depressed after his boyfriend broke up with him, but Ryder didn’t know how to talk to him about it. He knew Conor didn’t have many friends. His boyfriend had been his whole world – and now all Conor had was an inept roommate, staring awkwardly at his pain, unable to figure out the right words to say. But Alyssa had worked some kind of magic on him. She was so kind, and so helpful, and in time Conor started going out again. Ryder had been bewitched by her looks, but after seeing who she really was, Ryder fell helplessly in love with her.

Once Conor got out of his funk and became a happily single guy, and friend to Alyssa, he loved spending his free time poking fun at his roommate’s helpless crush.

‘Just talk to her! She won’t bite!’ he often teases. But for Ryder it’s not that simple. She seems to be able to make friends with everyone. Everyone except him. She and he are both Marketing majors and share a number of classes together, but they are worlds apart. She is remarkable, but he is astonishingly forgettable. That has always been Ryder’s curse. How many times has he tried to explain to Conor, that he actually has talked to Alyssa? He’s spoken to her a number of times! He just never leaves an impression.

As many times as he’s tried, Alyssa never seems to be able to remember him all that well. And it’s not just her. He’s been singing the same sad song most of his life. That is, until recently.

That’s because, as far as most people are concerned, Ryder is a pretty ‘meh’ looking guy… but he’s a damn cute girl.

He learned by accident, back in high school. A friend of a friend – Ryder has forgotten her name by now – was putting on a fashion show. She needed to make adjustments to one of her models outfits, but the girl was out of town until just before the show. The model was thin and none of the girl’s friends could fit the dress. That’s where Ryder came in. He was that thin. And, being the pushover he was, Ryder was somehow roped in to being this girl’s mannequin. But a funny thing happened.

The girl and his friend had so much fun dressing him up. Soon the girl wanted to see how he looked in her other outfits. Outfits led to make-up and wigs and shoes and accessories. It was embarrassing, but they were having so much fun, Ryder couldn’t help but have fun too. The day before her model came back for the show, Ryder and the girls had one last dress up session. The girl that was putting on the show took a picture with all of them and posted it to her various social media pages, with the caption:

Much luv to Ryder for filling in as my model this week. Couldn’t have done it w/out you! #theshowgoeson

Ryder was mortified. The idea of the ridicule he would receive made him want to hide his face forever. But there was no ridicule. The post got tons of ‘likes’. His real profile wasn’t connected to the image and no one seemed to realize that the pretty model in the picture, was a guy. For weeks after the post was put up, he stalked the comment section. Yet, the feedback was incredible. People congratulated the girl on her show and her designs, and remarked on Ryder’s good looks.

‘Great designs, beautiful model’

‘ZOMG so gorgeous’


The comments went on and on. As embarrassed as he was, the response to the post only served to solidify the feeling he’d had that entire week. It was a feeling of self-actualization he’d never received before. For the first time ever, he liked what he saw in the mirror.

He finally felt attractive.

Since high school, Ryder has experimented with lots of styles. He’s learned how to use and put on make-up and learned different ways to style his hair by watching YouTube beauty tutorials. He owns about 7 different pairs of high heels, and half the clothes in his closet are women’s. In the last few months he’s taken a huge step, sharing photos of himself on a separate Instagram account – and to no one’s amazement, it has more followers than his “real” account.

Alyssa is one of them.

Seeing her follow request made Ryder’s heart leap out of his chest. He’d even worked up the courage to send her a direct message, thanking her for the support. But her response, though cheerful and friendly, revealed a heartbreaking truth. She had no idea who he was. She didn’t recognize him – she just liked the pictures.

He’s been talking to Alyssa ever since, back and forth via direct message. With each new notification, he falls for her harder, but his anxiety grows. How would she react if she found out? She’s shown no acknowledgment that she’s aware of who he is. That he is Conor’s roommate, her classmate, or even a guy – a guy who likes her. And now, from their conversations, he knows that she’s considering switching majors. She will decide whether she’ll leave the School of Business while she’s home for break – and she leaves soon. If she does decide to switch majors, it means they won’t be sharing any classes and unless he stays roommates with Conor forever, there will be far fewer organic opportunities for them to talk. And so Ryder has decided that today is the day.

He needs to talk to her before she leaves for break. And to make sure he has the confidence to ask what he wants to ask, he needs to wear his armor and his war paint. He needs to be the person who likes what they see when they look in the mirror.

He’s never worn his armor around campus before. Only in the safety of his room and off campus for photo shoots. In his armor, he feels amazing. He stares at himself and smiles. Even his little sister has remarked that he is, ‘disturbingly pretty’ while dressed up. But just as quickly, she points out that, ‘no girl will want you though’ and Ryder’s confidence deflates like a sad balloon.

“I know this is out of the blue but, would you want to go get bite to eat sometime?” Ryder practices in the bathroom mirror – but the reflection looking back at him is unconvincing. He looks thin, pale, and scared. He is a tiny frightened creature that you take pity on, pat of the head, and then forget about as you go on with your life.

A swell of pent up anger and frustration bubble up to the surface as Ryder beats his fists against the sink. The pain ripples up his arms eliciting a painful shout.

“God dammit!” Ryder complains, shaking his now sore hands. “This shouldn’t be so hard. Why is it so hard?” Ryder sucks in a deep breath, to calm himself. He leans in to take a good look in the mirror, but his vision is blurry. His eyes are welling up with painful tears. From the pain in his fists? Not likely – but Ryder can pretend.

“Why is this so hard. What should I wear?”

The lump in his throat is growing bigger again and his hands won’t stop shaking. He takes another deep breath, trying to push everything down; the fear, the anxiety… the shame. That’s what it is. Shame. But of what, he’s still not completely sure. That he prefers the way he looks when he dresses this way? Or not being brave enough to admit it. He wishes he could look in the mirror and the confident, beautiful version of himself would look back and tell him to get his shit together.

‘Either do it, or don’t. Just stop being a damn crybaby about it.’ is what she would say.

So maybe…

Ryder wipes his wet eyes on his forearm and quickly goes to work lining up the desired items from his make-up kit. Methodical, practiced fingers make quick work, plucking eyebrows, applying foundation, contouring, applying blush, eye liner, and lipstick. He doesn’t want a dramatic look, so he goes light. Natural looking with a hint of flare – a bright lip color. With his face done, he moves on to his hair. He’s been growing it out, and it now hangs just past his shoulders, but he opts for the clip in ponytail instead for more volume. With each step the shaking eases.

Ryder looks in the mirror and waits. He sees the face of a pretty girl. The kind of girl he’d ask out in a minute if he could. But he’d probably get rejected. The idea of asking himself out and being rejected makes him laugh. It’s a nice smile. Open, warm, friendly, and attractive. ‘This is a confident, powerful woman. She’ll know what to do.’ Ryder thinks to himself.

He waits. But there is no else there. No confident powerful, female alter-ego. It’s just him, looking back at himself. A prettier version – but still just him. Just Ryder. He rolls his eyes and groans.

Ryder considers washing his face and starting over, but something stops him. His more confident female personality? No. Nothing like that. It’s just a guy, wearing make-up – not ready to turn back into a pumpkin yet. He looks at himself a little while longer. He really does enjoy the way he looks. He could primp and peacock in here all day.

“Yeah, I’d do me.” Ryder jokes.

He’s feeling the nerves again, but he shakes them away.

“She’ll either be open to it, or she won’t. Either way, I still look good.” He tells himself with a smile, but his insides are turning and coiling non-stop. He pushes through the fear, pushes through the shame of unknown origin and begins to dress.

***                        ***                         ***                          ***                            ***                      ***

Clad in a cold shoulder flowy blouse, skinny jeans, and three inch heels, Ryder steps out into the world, fully armored and generally confident. Most of the day goes by without much fuss. Conor is shocked to see Ryder’s choice of attire, but applauds his bravery. Ryder’s professors and classmates seem not to notice immediately, mainly because they don’t know who he is. There is at least one incident where a guy on campus flirts with him, and upon closer inspection realizes he’s a guy and throws a homophobic slur.

That rattles Ryder a little, but not enough to deter him from his mission. Alyssa.

She hasn’t been at her lectures today and he fears she’s already left for home. However, just as he’s ready to give up, he sees a familiar outline. Ryder’s heart skips a beat as he sees Alyssa standing with a few of her friends outside.

“Alyssa-” Ryder starts, but in his excitement, he trips over his heels and nearly breaks his neck. He looks around, immediately to see if anyone noticed. No one he cares about it seems.

Ryder straightens his clothes out and checks his make-up in the window of a nearby lecture hall door, before walking outside. His heart thuds non-stop in his chest, pounding in his ears and behind his eyes.

As he grows closer, his voice gets caught in his throat. He’s just a bundle of nerves, and her friends are right there. He wishes she were alone, but that may be asking too much.

“A-” Ryder tries to speak, but as her eyes lock on his, he freezes.

‘Grow a pair!’ an annoyed voice shouts in his head. It’s his voice. His confident voice.

“Hi Alyssa.” He finally manages to say.

“Hi.” Alyssa answers sweetly but obviously confused. Ryder can understand why. His face and voice don’t match. He can actually see Alyssa and her friends trying to compute who and what he is.

“You getting ready to head home?” Ryder asks, shyly.

“Uh, almost. Pretty soon.” Then, very suddenly, there is a flash of recognition. “Sorry girl! I almost didn’t recognize you… I didn’t realize you were a student here!”

Suspicion confirmed. Ryder feels flush and his ears burn with embarrassment. The way she addressed him as ‘girl’ can only mean one thing. She recognizes him from Instagram, but has no idea who he is. Not only that, the way she emphasized the word ‘girl’ – she can definitely tell he is ‘different’ and is probably trying her best to be use the correct pronouns. He finds it all the more endearing.

“Oh um, I’m not a girl.” Ryder smiles.

Alyssa’s friends do their best to hold back laughter as poor Alyssa’s eyes grow wide with horror and regret. It’s almost as though he can hear the tiny voice in her head screaming at her, ‘you had a 50/50 shot and you blew it!’ Suddenly, he’s feeling a little less nervous.

“I’m so sorry.” Alyssa apologizes, but Ryder can’t help thinking how cute she looks when she’s embarrassed. Regardless of how this goes, Ryder takes a moment to vow to hold this image in his mind.

“I guess this explains why you never said anything to me before.”


“It’s me. Ryder Bateman.” He pauses to give her a chance, but she appears to draw a blank. “Conor’s roommate.”

There is a moment, as Alyssa does a few mental calculations, where the silence is deafening. And then, all at once, her eyes shoot open once again with recognition. She stares at him a moment, completely and genuinely dumbstruck.

“Oh my God!”

“Hi Alyssa.”

“Hi. Ryder. Oh my God, I’m so embarrassed!”

“Wait, who is he?” One of Alyssa’s friends asks, curiously.

“Don’t we have like three classes together?” One of her other friends points out, drawing a triangle between the three of them.

“Something like that, I think.” Ryder nods in agreement.

“Wow, Alyssa, you’re the worst.” Her second friend teases.

“No, I’m sorry. I really am!” Alyssa’s face is bright red now and it makes Ryder’s heart melt. But when she gives him an apologetic hug, he stiffens.

“It’s cool, it’s cool” He says. “Actually, it’s kind of embarrassing but, I wanted to say something to you.” Ryder looks over at Alyssa’s friends wishing they would magically disappear or read the atmosphere and saunter off somewhere.

No such luck.

“What’s up?” Alyssa asks, friendly as always.

Ryder inhales deeply, willing her friends to go somewhere, anywhere else, but they don’t budge. They look on with deep interest.

“Look, I’ve really enjoyed being kinda Instagram friends, or… whatever… and…” Ryder searches for the least embarrassing way to say this, because he knows, now more than ever that he’s about to get rejected by the girl of his dreams in front of a flock of women. “Um… I think you’re great. I think you’re beautiful actually. Inside and out – ” and suddenly the words are falling out of his mouth  and he can’t stop them.

“Awe, thanks. You too – ”

” – I’ve thought so for a long time and I know you’re probably gonna say no – but did you maybe want to go out some time, or maybe just grab lunch or coffee… or something?”

Ryder’s body feels like it’s on fire as he looks at Alyssa’s dumbstruck face. He can’t read her expression. Confusion definitely, but something else. Whatever it is, it hurts his heart. His stomach coils and coils, making him feel sick.

He hasn’t been paying attention to her friends, but he nows at least one of them looks beyond disgusted. He doesn’t care though. Another of her friends seems embarrassed for her.

“You mean as friends?” Alyssa finally responds, but there’s a hint of an edge to her voice that Ryder just can’t handle. More certain than ever that he’s just made a huge mistake, Ryder backs away.

“I mean… I’m sorry, I shouldn’t have just ambushed you like that. I’m sorry…”

Without another word, Ryder turns on his heel and walks away as quickly as he can, back to his dorm, back to safety, before this chip in his armor has a chance to reveal itself.

***                     ***                    ***                    ***                    ***                   ***                      ***

The blue notification light on Ryder’s cell phone blinks rhythmically in the blackened room. He has been staring at it for nearly an hour, clearing his mind, allowing the periodic flashes to induce a hypnotic effect. His heart hurts. His eyes burn. He is exhausted.

Ryder lays in his bed, revisiting the events of that afternoon. Try as he might, he can’t get the sound of Alyssa’s voice out of his head. The edge of suspicion and… was it anger? Had he offended her? Ryder groans and turns in his bed.

He’d been ready to be rejected. He knew he would be. But he wasn’t ready for that suspicious hilt in her voice or that look in her eye. Remembering it makes all the other side eyed glances he’s gotten today feel so much worse.

And yet…

He is alive. Wounded, yes, but he’s made it through the day. He has walked around all day wearing what he wants to wear, looking the way he wants to look, and the sky hasn’t fallen down on him. His world hasn’t come to an end.

Ryder runs his hand through his disheveled hair, admiring it’s length. It feels good between his fingers, though it does need a trim. As he twirls the strands between his fingers, he considers a different style all together. What would look good on him? Lazily, Ryder reaches for his phone to do some impromptu research but pauses as he sees the source of the blinking notification light pop up on his lock screen. He has a new message. From Alyssa.

His stomach turns yet again and he remembers, for hundredth time that day, the look on her face when he asked her out. For a moment, he considers ignoring it completely – but that’s not him. At least, that’s not who he wants to be. He wants to be a confident person. An unapologetic person.

No personas. No alter-egos. Just him. Unapologetically Ryder.

So, Ryder does his best to prepare himself as he unlocks his phone and opens the Instagram app to see Alyssa’s message.

She writes:

Hey, I’m sorry if I came across some kinda way earlier. You just surprised me. I was a little embarrassed that I went all this time not recognizing you and once I did, I kind of assumed (cause of the way you dress) that you were trans, and when you said you weren’t a girl, I assumed you were gay so… yeah, wasn’t expecting all that at once. lol.

The message is simple, but fills Ryder with relief.

“She’s not angry.” Ryder speaks to himself quietly. Like a magical incantation, those words make Ryder feel so much lighter. He’s not just relieved, he’s floating. Riding the high, Ryder begins to respond back:

Hey. LOL no worries. It was probably a lot of info I dumped on you all of a sudden. I was afraid I upset you. Def didn’t mean to do that.

Ryder stops, considering for a moment if he wants to say more. Perhaps, he thinks, he should leave it at that? But something makes his fingers keep moving.

I’ve liked you for a while, but if you’re not in to me, it’s okay. I get it. Really. I just didn’t want to risk never saying anything to you, just cause I was scared of you saying no.


Ryder stares at the screen, proud of himself for saying that much. It’s the truth. He hadn’t expected much. Alyssa is too beautiful, with too many admirers to waste time on a guy she barely knows. Especially one in women’s clothes. She has so many options. But he still needed to try – to put his armor to the test. And despite everything, it all seems to have worked out.

Just as Ryder is about to put down his phone, a new message pops up. It’s Alyssa again, responding much more quickly than Ryder expected. He reads the message hungrily.

Can I ask a personal question? Why do you dress like a girl? You don’t identify as a girl, and I’m guessing you don’t identify as LGBTQ at all? Is it just, a hobby or is it an artistic thing? Just curious.

Ryder stares at the message and ponders for a while. For a moment, he wishes he could be self righteous and give an indignant ‘why do I have to have a reason’. But he can’t blame her. A few years ago, he would have wondered the exact same thing. Why would a ‘normal’, ‘average’, cis, hetero male, willingly submit himself to other people’s ire and vitriol, when he, technically, doesn’t have to.

He looks down at his nails, trim and painted with clear polish. He has tried for a while to understand himself why he feels compelled to dress this way. While doing research online, he’s come across a number of ‘crossdressing communities’ and was surprised to see how many self proclaimed straight men were there. Married men, with supportive wives. But these communities seem centered around a shared kink.

Ryder’s desire, he quickly realized, is not sexual. It’s vanity.

After mulling over her question, Ryder responds.

Because I like looking good. lol. I’m not trying to make a political statement, or channel my inner diva, or anything like that. I just want to be my best self.

Ryder waits, and within a minute, he has another message.

There are lots of diverse ways that guys can ‘look good’ tho. What drew you to that style?

Not an attack. Just curious.

Ryder looks at her message and laughs. He’s sure he’ll have to answer this question a lot going forward. But he’s oddly ready for it now. He writes:

It suits me

It takes a while for Alyssa to respond.

Fair enuf.

You’re def a knockout, so can’t argue. lol

And Ryder’s heart skips a beat. He thanks God that there is no one there to see the dumb grin on his face. Then, another message pops up.

I don’t think I’m secure enuf to date a guy that looks better in my clothes than me. I’m sorry.

But if you’re down, me and my housemates are throwing a party before I head home for break. Come thru! I may know a few girls that are a little more flexible than me.

The messages continue as Alyssa sends her phone number and details for the party, but Ryder is at a loss. On the one hand, the pain of rejection stings. Even though he knew from the beginning, it still stings to hear the final, ‘No Thank You’. Even the way she tried to soften the blow hurts. Actually, it probably hurts even more than if she’d just flat out rejected him. Ryder sends back a simple, ‘Thanks, I’ll think about it’ and turns off his phone.

In the darkness of his room, Ryder allows himself to feel all the pain and the lingering bits of shame and frustration that still reside within him. He’s done it. He’s donned his armor, and taken the beating that comes with it, and he feels stronger for it. Free of the anxiety he’s been carrying all day, Ryder suddenly feels incredibly tired.

As his eyelids grow heavy, Ryder thinks of Alyssa, and her clumsy invite. He has no intentions of taking up Alyssa’s invitation. It’s too much too soon. And besides, he doesn’t need a pity party. Then again, it is a good excuse to go out.

But that begs the question: What to wear?




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