Jeremy Jordan Imagines

Dressed Up For You-Winn Schott

I shifted uncomfortable in my heels as I watched people dance. I pulled at the skirt of my dress as I took a large drink of my champagne. "Whoa there, Sparky. It's not even 9 o'clock."

I looked up to see Winn walking towards me. "It's Friday night and I am spending it at a stupid work party where, only 45 minutes into the party my boss walked over to me, looked at my dress and said, 'that's it?' So yeah, I'm going to drink." I scanned his face as he let out a small laugh. "Shut up," I sighed, drinking the rest of it.

"Okay," he said slowly as he took the glass out of my hand. "Come on," he said taking my hand as he put the now empty glass on a nearby table.

"Where are we going?" I complained as my best friend led me onto the dance floor.

"We are going to dance," he said as he put his other hand on my waist. I couldn't help but smile as he rocked us back and forth to the music.

"How are you always so happy?" He seemed taken back by my question.

"What. . . What do you mean?" He stuttered.

"It's just you always seem so happy. At work, after work, even when Cat is chastising you about something that isn't your fault. I don't understand how you can be so happy, all the time. I just. . . I could never," I cleared my throat avoiding the sad eyes Winn was sending me.

"Y/N," he said trying to get my attention. "Y/N, please look at me." I finally looked up from our shoes. "Talk to me?"

"I just. . ." I looked at his eyes and got distracted.

"Y/N, please." He whispered. I bit my lip and nodded. Before I could start, Winn took my hand, intertwining our fingers and led me outside to the balcony. I subconsciously wrapped my arms around myself as I overlooked the city.

"Here," he said as he took off his suit coat and placed it on my bare shoulders.

"Thanks," I said softly.

"So," he said as he stood next to me and leaned against the railing. "What's going on in that pretty little head of yours?"

"Well," I said ignoring the red rising on my cheeks. "I can't really explain it. I guess. . . It's just. . . I feel. . ."

"Confused?"

"Yeah," I laughed.

"Empty? Frustrated? Like you're running in place, not going anywhere?"

"Exactly," I said slowly. "Winn? Can I ask you something?" I asked, turning towards him.

"Of course," he nodded.

"Are you really happy? Like are you actually happy or are you just really good at pretending?" I could see the shock on his face.

"What?" He faked laughed. "Why. . . Why would you ask that?" He chuckled nervously. I stepped forward and placed my hand on his cheek, making him look at me.

"You can tell me the truth," I said softly. He let out a small chuckle and reached up grabbed my hand. I smiled as he intertwined our fingers.

"I don't know. I'm just tired."

"Well, faking happiness can be exhausting." My comment made him look up at me and laugh. "But, I have to give you some credit. I could never fake happiness all the time. I mean, I can barely stand wearing a dress to a work party."

"You look amazing." He said making me blush again. "To be honest," he leaned forward to whisper in my ear. "The real reason I gave you my jacket was because I hate suits."

When he pulled away, I gasped as our noses touched. Before I could comprehend what was happening, Winn pressed his lips to mine. I hesitated to kiss him back, causing Winn to quickly pull away.

"I'm sorry, Y/N. I'm so sorry." He backed up a few steps as he began to ramble. "I can't believe I did this again. I misread, no no, I read too much into our friendship. Damn it. I did this with Kara and now I'm doing it with you. I'm so sorry, Y/N. I shouldn't have. . ."

I step forward and pressed my lips to his, cutting him off. He instantly pulled me tightly into his chest and started kissing me back. I let out a small laugh as his coat fell of my shoulders. My heart beat sped up as our lips moved in sync. When we pulled apart, neither one of us said anything.

I looked down and saw his suit coat on the floor. "Sorry about your jacket," I said still trying to catch my breath.

He just shrugged as he used his finger to make me look up at him. I mirrored his smile. "It's okay. Like I said, I hate suits." His comment made us both laugh.