Jeremy Jordan Imagines

The Bet-Winn Schott

Winn's POV

Y/N is the kind of girl who won't stop working on something until she thinks it's perfect. Every day this week I had to practically drag her home because she was so focused on the pages she was working on with James.

I watched as Y/N and James discussed the photo sheet and page outline that she had been working on all week. I smiled when I saw how excited James was and how revealed Y/N looked. I couldn't help but feel proud of her.

For about a year Y/N has been working as James's intern. At least that's what she calls herself, but she is pretty much his assistant. Suddenly, I felt someone stand next to me. "Hey Winn." I looked over when Mon-El said my name. He had a smirk on his face.

I don't know, but something about the smirk on his face made me want to hit him. I tightened my fists when Mon-El looked over at Y/N and, very clearly, checked her out.

"Is Y/N claimed?" Mon-El asked.

"I thought we talked about this," I sighed, trying really hard not to get angry. "You can't claim someone. It's. . . It's more complicated than that."

"Oh, I see." He laughed, cutting me off. He looked between Y/N and I, smirking. "You want Y/N all to your self."

At first I felt like denying everything, but something came over me. "Yeah? So?" I challenged.

I could tell by the look on his face, Mon-El had gotten an idea. "I bet I can get her to agree to go out with me before you can."

"What? I'm not going to bet on who can get her to go out with them. She's a girl, not a football game." I started to walk away, but stopped when he chuckled.

"Come on, Winn. It's a harmless game."

"Mon-El," I sighed, turning around as I ran my hand through my hair. I looked over at Y/N to see her laughing at something James said. "She isn't some bet, Mon-El. She's more than that."

"Winn," he copied my sigh. "It's not like we are going to hurt her or anything. She gets a free meal out of it and attention from two guys."

"No," I said sternly. "We aren't doing this."

*****

The next day, I walked in to see Mon-El talking to Y/N. He noticed me watching them and sent me a wink. I couldn't help but get jealous when I saw her smile at him and laugh at whatever he was saying to her. I quickly stormed off, heading to my desk.

"Winn?" I stopped when I heard Y/N say my name.

"Hey, Y/N." I smiled as she walked over to me. I saw Mon-El send me a knowing look. The only thing that confused me was that there was nothing for him to know.

"What's up?" I asked, ignoring his eyes on us.

"My laptop completely crashed last night and I lost everything I was working on. I was wondering if you might be able to help me recover some of it?"

"Sure," I shrugged. "I can do that. Let me take a look."

"Thank you! I'll bring it by a little later," she smiled, sounding relieved. "You're my hero," She smiled as she quickly kissed my cheek, before heading back to work. My cheek burned from where her lips touched.

"Well played," Mon-El laughed as he walked past me.

"I wasn't playing anything!"

Y/N's POV

I was typing on my computer, searching through some records when I was interrupted by Mon-El. "Hi Y/N," he said sing-songy.

"Hi Mon-El," I sighed, not looking away from my computer.

"I have a brilliant idea!" He cheered, making me jump.

"Your definition of brilliant or mine?" I mumbled, still not looking at him.

"How about we hang out?" He winked when he said 'hang out' causing me to look up from my computer.

"Hang out. . ." I said slowly.

"Yeah, you know. . . Hang out," he said in a suggestive tone, placing his hand on my forearm.

"Mon-El," I said slowly. "Let go of me."

"Come on, Y/N."

"Don't touch me," I said through gritted teeth. I tore my arm away from his grasp and stood up. I grabbed my phone and quickly made my way outside. As I stepped out of the building, I took a few deep breaths trying to calm myself down.

"Y/N?" I turned around to see Winn making his way out of the building and heading towards me.

"Hey," I stuttered. I ran my hands through my hair as he reached me.

"You okay?" He asked, softly. I noticed him hesitate before deciding not to do whatever he debated.

"Yes, no, I don't know. He just always. . . Whenever he. . ." My breath came out shaky.

"Hey," he said gently putting his hands on my shoulders. "Breathe."

I closed my eyes and took a few more calming breaths. "I'm sorry," I whispered, my eyes still closed.

When I opened my eyes I saw Winn looking at me with a soft smile. "You okay?"

"Yeah. Wow, I overreacted," I said with a small embarrassed laugh. "I should probably go apologize to Mon-El." I walked past Winn and started heading back to work.

"Nah," Winn laughed as he grabbed my arm, looping it around his. "He deserves to be knocked down a few pegs."

"You're awful," I laughed, playfully bumping him with my shoulder.

We walked back in silence, but right before we walked in Winn cleared his throat. "Do you umm. . . Would you want to. . . Do you want to maybe go get dinner sometime?"

"Yeah," I smiled. "I'd like that."

*****

I was about to leave work when I thought I heard someone say my name. I walked around, trying to find the person but couldn't. I was just about to leave when I heard someone say my name again.

This time I recognized the voice as Winn's.

"I don't know how many times I have to say this Mon-El, but I wasn't trying anything."

"Whatever you say," Mon-El laughed. "You still won."

"You won?" I laughed, coming around the corner. My eyes narrowed when I noticed them jump. "You won what?" I asked slowly.

I looked between Mon-El and Winn, watching as they nervously glanced at each other. Suddenly it all made sense. Mon-El wanting to "hang out". Winn finally asking me to dinner.

"It was all a bet," I whispered. They didn't have to confirm that it was true. Their facial expressions said it all.

"Wow," I sighed, tears blurring my eyesight.

"Y/N just let me explain," Winn said as he stepped towards me and grabbed my wrist.

"Don't," I interrupted him, instantly pulling my hand out of his grasp and taking a step away from them. "I understand everything. I was just a bet to you. You don't actually care about me," I said, the tears finally streaming down my cheeks. I didn't even try to stop the tears as I saw the look on Winn's face.

"No," he said shaking his head. "It's not like that."

He tried to take a step towards me, but I instantly took a step back, getting ready to run.

"Yes it is," I said angrily wiping at the tears. I looked back up at him, glaring as my eyes filled with replacement tears. I bit my lip as I slowly started backing away towards the door. I had one last thing to say to him and after I said it, I was planning on running away and never looking back.

"You just lost more than a bet."

Part 2 Coming Soon