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You Know What Trope Is Happening

We pull up to the hotel. It's extremely elegant looking. As we walk into the lobby a woman at the desk smiles at us.

"Hello, are you here to check in?" She slides over to her computer and opens something up.
"Yes, the room should be under either Enderson or Grima." Leo leans over the counter, looking at her. She begins to type some things in.
"Ah, Cas Enderson?" I nod. She smiles and slides a key over the counter to me. "You'll be on the 11th floor, room 8." She turns her attention to Leo. "Now let me see for you... Grima, Grima.... Hmm. I'm not finding anything under that name, Mr. Grima."
"Oh, we'll be sharing a room, thank you." I smile at her and begin grab my briefcase. She raises her eyebrow then gives a slightly forced smile.
"Oh! Well you two have... fun." Leo awkwardly nods and we head to the elevator.

In the long elevator wait we stand awkwardly.
"Haha, she looked at us weird huh?" I nervously chuckle, trying to break the silence.
"Yea, I think she wasn't expecting us to share a room. Since we're coworkers."
"I guess that's fair. It's weird that your name wasn't even on the check-in list. What if I let you have the room?" Leo's expression doesn't change.
"Well, I guess Elliot assumed that I'd be nice and give it to you.... Or maybe he just wanted you to have it in the first place." I'm about to say something when the doors chime open.

We walk down the hall, passing several rooms marked Do Not Disturb until we reach the eighth room. I swipe my keycard and open the door. I walk in and turn on the lights.
"Oh.... Um." There's only one bed. [( ͡° ͜ʖ ͡°)]

Leo walks in and sighs. Without missing a beat he places his bags in the chair in the corner.
"I'll take the floor." His tone sounds a bit irritated.
"I- I'm sorry. I really thought-"
"It's fine. Whatever. Do you need to go buy you clothes?"
"Oh, yea but I can do that by myself, and I can get you another room somewhere too, or I can get a new one, or-"
"Cas. Really. It's fine. Let me know when you're settled in so we can go shopping." He turns to pull a few things out of his bag and places them on the desk. For this room only having one bed, it's really big... and nice. This must have cost a fortune. My thoughts are interrupted when Leo pulls a piece of paper out of the desk drawer. After a second of looking at it he scoffs. "Huh." He shakes his head as he hands it to me. It says "Have a wonderful stay, Cas! I look forward to working with you - Elliot Kamski"

"Huh, what's up with that?" I turn the paper over in my hands.
"What's up is that I think you're the favorite. And he wants me to know it." Leo stares down at the desk.
"Why would I be the favorite? And what does he have against you?" After a second, Leo rolls his shoulder, shrugging.
"Who knows? Well, that's just the way it is I guess. You ready?"
"Oh! Oh, uh, yeah."
"Great. Let's go." Leo swiftly walks towards the door, not even looking at me. I speed walk after him, struggling to keep up after locking the door.

About 20 minutes later, Leo and I walk into a mall together. I begin to make my way towards Macy's and JCPenney when Leo stops me.
"What are you doing?" I look at his, confused.
"Going to.... buy... clothes?" He shakes his head.
"The company's paying for this, and you're not going to use this opportunity to buy nice designer clothes?" He makes a good point. This might be my only chance to get such fancy clothes. (If this were episode, this would be where you'd have to pay 30 diamonds to not wear literal rags.)

We walk over to some luxury stores on the upper floor of the mall. Leo stops in his tracks and points at a window display.
"Do you like that?" I turn to see him looking at a really expensive looking pinstripe suit.
"Wow, it looks really nice."
"Alright." Leo quickly turns and walks into the store, and flags down the first store assistant he sees. "Excuse me, they'd like to try on that suit you have displayed." The assistant looks over at me and nods.
"Alright, you're about a small, medium? I'll bring both out just in case. Be right back." She turns and walks to the back of the store.

"Really it's fine, I'll never have anything to wear it to anyways." Leo looks over a nearby shelf, picking out a few shirts in his size.
"Maybe, but it's better to have it in case you ever have to wear it. You need casual dress shirts?" I nod, looking through a rack of ties. After a second, Leo strolls over with a few neutral and pastel shirts, then also looks through the ties. He pulls out the most hideous tie I've ever seen; a zebra print with smiley faces all over it. It's marked 75% off. He holds it up to his chest.
"What do you think? I don't know if I can pass up such a generous deal for such an amazing tie." He raises his eyebrows at me, modeling the tie. I rip the tie from his hands throwing it back on the shelf.
"Don't even joke about that." He chuckles as he hands me the shirts he's been holding.
"Try these on in a minute." They're pretty decent.

The shop assistant comes back, handing me a suit set. They gesture down an aisle to the dressing rooms and escort us both there. Leo and I both go into our own respective changing rooms. Before I go in, he tells me to try on the suit last, and to show him before I change out of it. I try on all of the shirts he handed me, they fit perfectly. I never told him my size. Well, I guess he could just look at me and guess, but still. I slip one of the suits on, the pants are a bit big, but the jacket fits me perfectly. I switch the pants out and look in the mirror. I feel awkward. The suit looks good, but it's discredited since it's on me.

"Leo, the suit fits." I say to the dressing room wall.
"Okay, I'll be out in a second." I go out into the hall and look at myself in the mirror. As I stand there, the shop assistant passes by, then backtracks, and gives me a thumbs up while mouthing "wow." I chuckle as she walks away and hear the dressing room door crack open. I turn around and see Leo standing with a loose button down lightly tucked into some high waisted pants. He looks really good. He looks surprised when he sees me.
"Wow. I say you get it. You look good." He sounds a bit indifferent. I turn back to the mirror.
"Yea, I just feel like a dress might suit me better? I don't know. You look really good though." He stands next to me in the mirror.
"Thanks. Oh! Speaking of dresses..." he turns back to his dressing room and grabs a dress bag, holding it out to me. "While I was browsing I saw this and thought you might look good in it. Do you want to try it on?" I take the bag from him, tilting my head.
"Sure, why not?" I turn back to my dressing room to try it on.

I unzip the dress bag to reveal a floor length, dark blue satin gown. I know I said a dress would fit me better, but I somehow feel weirder about this than the suit. I quickly slip the dress on then step out of the room. Leo turns around a gives a small smile.
"How do feel about it?" He watches me carefully as I look in the mirror.
"It's nice, but it feels a bit too fancy for me." I give him a weak smile as he scoffs.
"I think it looks great on you. How about this, we get you the suit and the dress and you can wear either one to the party this week."
"... Alright." After I change back into my clothes we make our way to the register and buy our outfits. We spend the rest of the day talking, window shopping, and buying food.

Ok I know that wasn't a great way to end but this is getting long sooooo

When Cas thinks they don't look good in fancy clothes.