Go Big or Go Homeless

“I’m going to die alone, man.” Skylar Ellison was quite intoxicated, as was everyone else standing on that green steel balcony dangling over Lafayette in the French Quarter, in New Orleans, Louisiana. It had been January first for about five minutes, and nearly everyone at the party had someone to lock lips with, save one particularly sad recent college graduate. The uniquely awful feeling completely alone in a crowd full of people permeated his very being, not helped by the fact that literally everyone in attendance could better be described as one of his roommate’s friends, rather than his own.

Realizing no one was actually listening, he couldn’t help but interrupt a moment of romance between some random pretty redhead, and her beau. He poked them both not so subtly, and slurred, “How do you do that?”

“I’m sorry?” the girl replied, while her boyfriend snickered at the scrawny twenty-something, swaying back and forth, splashing beer all over the concrete floor. He seemed to be held up by sheer force of will rather than a functioning sense of balance.

"Love?" the drunken youth asked no one in particular, before deciding he agreed with himself. “Yeah, love. How’d you find love? I mean, I’m like…nice…I’ve got stuff to offer…I think. Where’s my happily ever after? Nevermind, you don’t care.” Skylar began to turn and stumble away, trying to decide if he should ambitiously aim for his bedroom, or if it was worth waking up on the couch with male genitalia drawn on his face, just to save a few steps.

“Wait,” the girl said, grabbing the short boy by the arm and turning him back around. The blurry image of her face fueled his uncertainty. Was that a flicker of understanding in her eyes, or simply a reflection of the city lights? “I care. I know exactly what you’re going through. You might not believe me, but I know exactly what you’re going through. I never thought I’d meet someone who makes me as happy as him.” The girl kissed her boyfriend on the cheek, seemingly desiring more, but not wanting to rub the troubled mess’ face in her obvious jubilance.

Skylar was incredulous. “HA! Yeah right! A hot chick like you? No way.” After the drunken youth blew a raspberry in her face, it was clear she must have been built of infinite patience, or at the very least, found his sorrow supremely relatable.

“You’d be surprised.” the girl replied, rolling her eyes.

Like a moth drawn to a flame, the boy's path led him inexorably towards the bait. Resistance was futile in the face of its irresistible pull. “Okay, fine. Tell me your secret.”

“It’s simple. Last year, I made a New Year’s resolution, and I stuck to it. I said I was going to find love, and held myself accountable.”

Skylar scoffed, “You’re fucking kidding me. What a laugh. Besides, nobody ever keeps those things anyway. It’s just some shit people tell themselves when they’re riding the high of the ball drop, but everyone turns their treadmill into a very expensive coat hanger sooner or later.”

“No, I’m serious. You don’t believe me?” Skylar shook his head. “Here, give me your phone.”

With a shrug, the youth complied. The girl pulled up an app in the store, one with an incredibly rare, perfect five star rating. “I used this last year, and it really worked. You fill out the forms, give them your resolution, your self-imposed deadline, and then whatever collateral you feel confident enough to put up. If you don’t succeed, they keep the money, or whatever, but that’s the point. It’s an excellent motivator. Like, it literally forced me to stay accountable to myself.”

As drunk as he was, Skylar was still apprehensive. It all sounded a little too good to be true. “I dunno. That sounds like a scam.”

“It’s really not. Just look how happy we are now. You said so yourself, right?” Her smile was a siren song, and his defenses crumbled under the dazzling assault of her pearly whites. Before he could think twice, Skylar found himself hitting download, lost in the moment's euphoria.

Speedily scrolling through the terms and conditions, clicking agree, agree, agree, he finally reached the moment of truth. Resolution. A moment of pondering, and a light bulb lit up above his intoxicated head. “I’m going on a Valentine's Day date this year. Like, I’ve literally never done that before. God, saying it out loud, I feel like such a loser.” Next was collateral. “Ummm…actually I don’t really have any money. Just like…my car.”

Most people, even Skylar, would have thought better of it then after remembering that fact, but hearing the simple provocation from the girl’s boyfriend, “Go big or go home, bro.” was enough to seal the deal. Proud of himself, he climbed back inside through the window, and opted to fall asleep on the couch, face sketches be damned.


“I’m sorry, Skylar, but you can’t stay here anymore, at least not for free. The rent in this city is too damn high already, even without a deadbeat roommate refusing to pull their weight. Look, your name isn’t on the lease, and you’ve contributed absolutely zero dollars since we agreed to let you stay here, so that means, you’ve got to go. I mean, fuck dude. You even eat all our food. I know you’re not like, a total piece of shit, but everyone’s got their limits. End of the month. Discussion over.”

The look on his best friend, and roommate’s face told the boy she meant business. “Please, Rachel. I’m trying my best here. It's just like, you know…nothing’s been a good fit.”

“Oh, that’s bullshit, and you know it. You’re just too picky. Sometimes you’ve got to do shit you don’t want to do. Do you honestly think it was my lifelong dream to work for a staffing agency? Look, I’ve tried to help you a dozen times now, and you’ve always got an excuse. Kelsey and Brianna agree, but when it comes down to it, it’s my ass on the line if the rent doesn’t get paid, so it’s my decision. If you want to hate anyone, hate me. End of the month. You’ve got two weeks. Figure it out.”

Rachel felt guilty as she stormed to the door, but tried not to show it. A glance back at Skylar, hanging his head in shame almost got her to change her mind, but enough was enough. “It’s for his own good.” she told herself. “That boy’s never going to do anything different without a kick in the pants.

Having grown up in a particularly affluent family, Skylar didn’t have a lot of experience with real discomfort. Being expected to do something he didn’t want to do seemed like a completely foreign concept. Not wanting to major in business, he switched to history, and completed his bachelor’s degree without mention to his parents. By the time they found out, needless to say, they were furious. Being cut off financially for the first time in his life, the young man found sympathy from his three best friends from university.

He didn’t want to move back to Seattle, so they offered him a room, and Rachel, in particular, took advantage of her position to help find him employment. The museum was too stuffy. The temp job at the docks was too strenuous. Being a waiter didn’t pay well enough, though that didn’t make much sense to the girls when no pay was the alternative. Truthfully, they just weren’t his dream job, and quite entitled, Skylar couldn’t bring himself to settle for less. It may have sounded silly to most, but what the boy truly wanted was to work for one of the many haunted tour companies that populated the Big Easy, but somehow none of them ever seemed to be hiring.

The air itself seemed to press down on Skylar as he collapsed onto the couch, a physical manifestation of his defeat. His eyes traced the cracks in the ceiling, their imperfections echoing the fissures in his own resolve. He thought to himself, “At least I’ll be sleeping in an Audi.” It was a gift from his grandparents, his last remaining worldly possession worth anything, the others being a half ruined mattress, a busted laptop, a smartphone with a past-due bill, and a suitcase full of rapidly decaying clothes.

Just then, a soft chirp from his phone nudged him out of his contemplation. There was a notification from an app he didn’t remember downloading. It read, “It’s February 13th, and you have one day remaining to complete your resolution. As a reminder, failure will result in the confiscation of [2022 Audi A6]. If you need any help completing your goal, please reach out to one of our customer service specialists who will be happy to assist you in any way they can.”

Reading the form notification, the events of New Year’s eve came flooding back into the panic-stricken boy’s mind. “They can’t seriously hold me accountable when it’s that easy for a drunk person to click their way through that nonsense. Jesus Christ!” Quickly, he opened the chat function, and began furiously typing.

Skylar: You guys can’t take my fucking car!! This is insane!!!!

It took a moment, but eventually those three tell-tale dots let him know someone on the other end was formulating a response.

Cup: Hello, Skylar. Hope you are well. Thanks for using Resolve It or Lose It. Please tell me what I can do to improve your experience.

Skylar: Are you kidding me?! You can cut this shit out, and stop threatening to take my fucking car

Cup: I’m sorry Skylar, but our terms of service were very clear, and our contract is legally binding. What can I do to help you complete your resolution?

Skylar: How would you even know where it is

Cup: Right now it’s parked on Lafayette, outside of your apartment.

Skylar: I’m just gonna move it. What then

Cup: Moving it to Royal won’t matter.

The fact that was the exact place he was thinking of creeped out the rage-filled youth enough to disarm him. He tried to rationalize it as a lucky guess, but still, it wasn’t enough to assuage his anxieties.

Skylar: Look, seriously, I can’t lose my car. I’m about to lose my place to stay already and I’ll die if I have to sleep on the street. This feels like a scam anyway

Cup: It’s not a scam, Skylar. It’s preferable to myself and the company that you get to keep your vehicle. I assure you, we started this company with one goal, to help our customers achieve their dreams. Like I said before, I will do everything in my power to help you do just that.

Out of options, the boy sighed, and decided to just do whatever the chat said.

Skylar: Whatever. Just tell me what I need to do

Cup: Right, give me one minute to review your file please, and I’ll be right back with you.

Skylar let out a groan, and shut his eyes, waiting on pins and needles for whatever came next. The chime sounded.

Cup: Okay, you stated in your resolution that you would go on a date on Valentine’s Day. Simple enough. The first thing I’d suggest is we set up a dating profile for you on our company’s sister app, Lovestruck. It’s very service oriented. You won’t have to lift a finger. I can take care of the ins and outs, but we’re going to need to clean you up a bit. You seem to be a little rough around the edges right now, and I doubt there’ll be much success if you’re not putting your best foot forward. I’ve set up a visit at a nearby salon for you, to correct the problem. They come highly recommended. I’m sure by the time they’re finished, you’ll be well on your way to feeling like a brand new person.

Skylar couldn’t remember sending a photo, but that night was a blur, so he had to assume it was part of the whole thing. None of that changed his current financial situation.

Skylar: I can’t afford that Cup. I can’t afford anything right now, remember. What kind of a name is Cup, anyway??? Like for drinks???

Cup: Not exactly. It’s a nickname. You’re probably saying it wrong. Anyway, don’t worry about the cost, Skylar. It’s all included with the service. Head to the address I’m forwarding to your email. You just have to show up, and they’ll know exactly what to do.

The youth tried in earnest, but couldn’t make sense of any of it. “How the hell does this company make any money?” he wondered. Whatever the case, it wasn’t like he had a choice.

Skylar: Okay fine. Leaving now


A quick drive across town to the Garden District, and Skylar arrived to his destination. He was expecting a typical, possibly bougie, unisex salon, but the pink, stylized, neon lettering on the sign reading, “Venus in Curls” told him it was anything but.

“You must be Skylar!” the middle-aged buxom blonde with an oversized bouffant said, as she welcomed her new customer in before he even had a chance to introduce himself. She pulled him tightly into an uncomfortable hug, smushing the much shorter boy’s face into her leopard print dress, and ample cleavage. “I’m Vennie. Nice ta meetcha. Cup told me you were a cutie, and he wasn’t kidding. Come have a seat, and we can get started. Would you like some cucumber water?”

Skylar shook his head, nervous to accept anything from the extremely alien establishment. He found the woman beautiful, not at all diminished by her advancing years, thinking to himself, “She’s no Helen of Troy, but I could still see someone going to war for her.”

“Okay then,” the woman continued, “let’s take out that ratty ponytail, and see what we’re working with.” Vennie ran her fingers through the tangled brunette locks, and twisted them around every which way. Whatever she was thinking brought a smile to her face. “Maybe I’m biased, but I’m thinking blonde and wavy. Perhaps a little retro. We can definitely do something with those gorgeous lips and cheekbones. You’re not very big, so C-cup, perhaps a B-cup? What do you think?”

“Wait, wha…?” Skylar was flummoxed.

The woman explained, “For your makeover.”

“I’m sorry, but I think there’s been some kind of mistake. Would you give me a minute?” Vennie stepped away, and the confused youth returned to his phone.

Skylar: There’s been some kind of mistake Cup. This lady seems to think I want to be made up like a girl or something

Cup: No mistake, Skylar. We need to get you on that date tomorrow, and don’t have much time. Did you know women are five times more likely to get a message on most dating apps? You said yourself, you absolutely can’t lose your car. This is the most efficient way to prevent that.

Skylar: That makes sense but I’m not a girl

Cup: I know that, but given the circumstances, I thought this was the best way to achieve your goal. It’s only for one date after all.

Skylar: There’s no way in hell I’m doing that

Cup: If that’s your decision, I understand, but failure to complete the resolution will result in confiscation of the vehicle. I’m sorry but my hands are tied.

Skylar pinched the bridge of his nose, a headache firmly pounding in his skull. He took a deep breath, and accepting he was at the mercy of this crazy company, decided to comply.

Skylar: Okay fine but this better work Cup

Cup: Satisfaction guaranteed.

Skylar didn’t exactly believe that, but despite his best efforts, he was unable to think of a better option.

In short order Vennie returned to her task, and within the hour, Skylar was staring at his reflection through the salon mirror, though it didn’t look anything like when he walked in. His very blonde hair was wound up in large rollers on top of his head, his countenance painted up like a glamorous starlet, complete with dramatic eyes, and plump ruby-red lips. The stylist’s effusive praise while putting the finishing touches on his new glossy talons was little comfort as he struggled to make sense of what had got him there in the first place. He almost ruined the manicure, nearly jumping from the chair, startled by the sound of his phone ringing.

“Skylar, hey. Look I’m sorry I got so mad earlier. You seemed pretty down when I left. Are you okay?”

Happy to hear Rachel’s voice, Skylar felt a sense of relief wash over him. “Yeah, umm…” Though his reflection told him otherwise he continued, “I’m okay. What’s up?”

“Well, I don’t know if it’s fate, or whatever, but I just had a job come across my desk, and I’m positive you want to hear about it first before I throw it up on the board. New Orleans Houses of Horror is looking for a new tour guide. Period dress. Great benefits. Education is a plus, so you’ve got some room to negotiate your salary. It’s all good news. I mean it though. This is your last chance. Don’t fuck this up. The interview is at four. I’ll tell them you’ll be there with bells on, okay?”

“Umm…actually, Rachel…I…”

“You’re not seriously gonna blow this, are you?! I swear to god, Skylar…!”

“No, I’ll be there…” the now gorgeous boy relented. “Just text me the address.” Groaning as he hung up the phone, Skylar let his head fall backward` only to be stabbed in his tender scalp by the velcro rollers for his troubles.


After work, Rachel was sitting on the couch thumbing through a magazine, when suddenly the door swung open. In walked a striking blonde girl she didn’t recognize, her arms laden with garment bags. She liked her style, the platinum strands teased just a smidge to give the do a little height, spilling down to her shoulders in gentle curls. Her immaculately made-up visage gave hints of Marilyn Monroe, and her outfit, consisting of black capris, and an off the shoulder white blouse could only be worn that far south in the month of February. Somehow she wasn’t toppling over strolling inside in those platform sandals with three-inch heels.

“Miss, I think you have the wrong apartment.” Rachel said, positive she locked the door. Only after getting up to help the poor girl did she recognize the face under all that makeup. Her jaw hit the floor. “Skylar, what the hell happened?!” The question carried genuine concern, but that didn’t stop it from being accompanied by tear-inducing laughter. She grabbed a piece of luggage to lighten her friend’s load, and was astonished by the weight. “What’s in this thing?”

“Okay…” Skylar held up a polished finger while he caught his breath. Finding his composure, he explained, “That’s my costume for work. I got the job.”

“That’s great!” Rachel unzipped the bag to find an antebellum period ensemble, complete with foundation garments, and a quality wig done up in sausage curls. “Is that why you’re…” she waved her arms around her bestie’s body. “...you know.”

“No, this is for my date tomorrow night. The salon lady gave me this outfit because she said I’d look weird if I left in my own clothes, and I’ve got another dress right here.” He held up the second bag and then carelessly dropped it on the floor before collapsing onto the sofa.

After going over his story in every excruciating detail, Rachel couldn’t believe the farce. Skylar had lived it, and he couldn’t quite believe it himself. The tale finished, the two shared a laugh at the absurdity of it all.

Skylar went on, “Anyway, I hope I can keep this job, when I tell them I’m a boy. I don’t know what info you got, but apparently they were only looking for women this time, anyway. I mean, I was just so happy to get some good news, but I can’t seriously be expected to do this every day. Hopefully it all works out.”

“Absolutely not.” Rachel replied. Her glare let him know she was serious. “ I meant what I said, Skylar. This is your last chance. If they want you to wear that dress, you’re gonna wear that dress, at least until you find another job. If you quit, there’s nothing else I can do for you.”

He wanted to argue, but with no energy left, he could only whimper, “Fine.” and then got up to go lie down in bed.

Before he could leave, Rachel asked, “What about tomorrow, though? You’re supposed to go on that date, but won’t your hair and makeup be wrecked by then. I don’t know about you, but I can’t recreate that. I mean, shit, dude. You look like a completely different person.”

“I know, right?!” The feminized boy gave a shrug. “I asked that lady about it, and she told me not to worry. Said it was guaranteed to last until then, and if I wanted a touch up or lessons, to come see her. I almost laughed in her face, but she was so nice I couldn’t bring myself to.”

“I’ve never heard of anything like that. Must be magic.”

“Must be… Anyway, I’m pooped. Talk to you later.” In bed, Skylar tried to go to sleep, but couldn’t stop himself from playing with the bouncy breasts glued to his chest. They seemed so lifelike, and he couldn’t remember the last time someone else let him play with theirs. He asked himself, “How the fuck did I let this happen. Like, a sane person wouldn’t have walked out of that salon looking like this, let alone went there in the first place. I must be losing my mind.”


February fourteenth had arrived, and Skylar found himself standing out front of a quaint little French restaurant hidden nicely down a little alley. All things considered, he still felt a little overdressed, wearing a tea-length, sleeveless, boat-neck dress inspired by Dior’s classic new look, flaring out over a sewn-in red tulle crinoline. His ten glossy red toes, peeking out from the equally glossy red peep-toe pumps, perfectly matched the color of the dress, itself decorated with a plethora of tiny black polka dots. A simple black belt, black chandelier earrings, and a tasteful glittering black clutch, were the perfect accessories, creating a Valentine’s date look, inspired by old Hollywood glamor. Somehow, the picturesque makeup, and bouncing bouffant hair were still firmly in place, just as Vennie had advertised, illogical as it seemed.

Never getting to use the app himself, Skylar had yet to even see the guy he was to be spending the evening with. Cup, playing secretary, insisted they’d be a good match, even though the customer service rep only had a few snapshots from Vennie, and his client’s reluctant attitude to go off of. The only information the boy turned girl had been given was to look out for a handsome man in a suit, carrying a single rose.

“How the hell am I supposed to know if he’s handsome?” Skylar thought to himself. “I’m attracted to girls. Dudes are just dudes, right?” One look at the guy as he approached answered that question for him. The pope himself may very well have tried to bed the man.

“You must be Skylar.” the striking young man said, as he approached and offered the flower. “I’m Mark. Nice to meet you.”

Skylar didn’t say a word. He just stood there mouth agape, wondering what this long lost Hemsworth was doing giving him the time of day. At that moment, he almost could have sworn someone had shot him in the ass with a heart tipped arrow.

“Sorry, are you not Skylar? I’ve really cocked this up, haven’t I?”

“Oh no, sorry. Yes, I’m Skylar.” The pretty youth accepted the flower, gently sniffing it, letting the petals tickle the tip of his pert little nose. In spite of himself his heart fluttered. When the young man offered the crook of his elbow, Skylar actually wanted to take it, briefly forgetting the absurdity of the situation.

Inside at the candlelit table by the window, a miracle reservation to get on such short notice, the two perused the menu, stealing glances at one another nervously. Mark’s desires hardly masked, the normally dense skylar found himself feeling desirable for the first time in his life, though not in a way he’d ever imagined. Suddenly very aware of himself, he threw up the wall, cleared his throat, and tried his best to decide between the duck, or the chicken.

After the pair placed their order, with a mental barricade erected, the delicately dressed youth tried to make polite conversation. “So what do you do, Mark?”

“Oh, I’m a doctor. I’m doing my residency at the children’s hospital across town, and I plan to specialize in pediatrics when I’m finished there.”

“Good god! I bet he’s got a hundred rescue dogs, and he calls his mother every day, too.” Skylar thought to himself, instead asking a different follow-up question, “Any hobbies?”

“Just rugby.” Skylar assumed he had the guy figured out now, but he continued, “I mean, there’s something else, but you’d think it was silly.” It was strange for the skirted boy to see an all too familiar look of insecurity on the face of a person he wasn’t completely certain to not be chiseled from marble. “Enough about me though, what about you? What do you do?”

“Oh…well I haven’t started yet, but Monday, I’ll be the newest tour guide for New Orleans Houses of Horror, doing ghost tours and the like.”

“No. Fucking. Way!” A gleeful expression spread across Mark’s face, devouring any twinge apprehensiveness felt between the two. “You’re not going to believe this, but I genuinely think that’s the coolest thing I’ve ever heard. I absolutely love paranormal history. Seriously, I’ve lived here for years, and I still take one of their tours at least once a month. That’s what I was too embarrassed to tell you. Most people look at you strangely when you tell them you’re into ghosts. How did you get into that?”

Taken aback by the guy’s sincerity, it took Skylar a moment to answer. “Oh, I umm…I majored in history with a focus on folklore.”

“That’s so cool! Your parents were supportive with that?”

“Absolutely not.” he chuckled.

You’re a brave girl, aren’t you? Far braver than me, at least.”

Skylar smiled brightly, and twirled a strand of hair around their finger demurely. “Yeah, I guess I am.”

Skylar didn’t find it strange when they referred to themselves as a girl. Nor when they went for a walk afterwards, talking into the night, despite several hours prior receiving a notification that read, “Resolution completed. Thanks for using Resolve It or Lose It.” Nor when they held hands as they headed back to their cars. Especially not when being kissed goodnight, and their foot kicked up behind them, just like in all of those old Hollywood movies. In fact, it was something they were very much looking forward to getting used to.


At the next New Year’s party, a sad young man was out on the balcony of a certain New Orleans loft, lamenting his misfortunes. A pang of loneliness shot through him as the countdown reached zero, his eyes drawn to a radiant couple locked in a passionate kiss. He felt like a forgotten footnote amidst the joyous revelry. Speaking to no one but the heavens, he asked, “How the hell will I ever be as happy as those two?” surprised when the pretty blonde gave him an answer.

“Well, last year, I made a New Year’s resolution, hoping to find love, and after sticking to it for once, it actually paid off.”

The girl didn’t seem like she was screwing with him, but he still couldn’t quite believe it. “Those don’t really work though, do they? I mean, they’re just nonsense people tell themselves to feel better until they inevitably break them and feel like shit all over again.”

“I used to think that too, but look at me now. Here, give me your phone real quick. There’s an app you have to try.”

Somewhere up on a mountain, there sat a chubby little baby in a diaper, fluttering around with his tiny wings. Checking his computer, he clapped his hands together, and shouted over his shoulder, “Looks like we got another one, bro!”

“Seriously, Cupid?” Deimos, the manifestation of fear and despair asked, genuinely surprised the mortals kept falling for his brother’s convoluted schemes. “Wasn’t the whole bow and arrow thing, easier?”

“Yeah, but Mom didn’t get to have as much fun then. She’s gonna love the baby fat on this one’s cheeks. Nice tushy too. Oughta be quite pretty when she’s done with him. You know me. Can’t disappoint mom.”

“I guess so, but this still seems kinda ridiculous. I mean, you used to flutter around two, maybe three days tops, to fill your quota. Now you’re spending months in front of that thing, click clacking on all those buttons, like some kind of human. And seriously, what’s with all the boys in dresses?”

Cupid shrugged. “Eh, it was getting boring the other way. Listen bro, you just keep setting them up, and I’ll keep knocking them down.”

If you liked this post, you can leave a comment and/or a kudos!
Click the Thumbs Up! button below to leave the author a kudos:
79 users have voted.

And please, remember to comment, too! Thanks. 
This story is 5146 words long.