Jeremy Jordan Imagines

I'll Be There For You-Winn Schott

Dedicated to MadamCephas
I got a little carried away with this one lol #sorrynotsorry? Also, I couldn't resist the Friends reference in the title. Requests are open!

I jolted awake when my phone started to ring. I looked at my clock to see it was 11:52 pm. My eyebrows furrowed when I read the caller id.

IT Dork 🤓😎

Why would Winn be calling me so late?

I sat up, unplugged my phone from the charger, tucked my feet under me and answered. "Hello?"

"Oh shit. Sorry Y/N. I. . . I didn't mean to wake you."

"It's fine, Winn. Is everything okay?" I asked nervously biting my fingernail.

"Ummm," he hesitated.

"Winn?" My heart stopped when I heard him let out a sob. "What's going on? Are you okay?"

"Can you come to your front door?" He asked softly.

"What? My. . . Um yeah. Give me a second." I quickly got out of bed and headed down the hall to my front door, still on the phone with Winn.

When I opened my door, my heart sank. Winn stood on my doorstep with red eyes, messy hair like he had been running his hands repeatedly through it, and the same clothes he wore to work. His tie was loose and the first two buttons of his shirt were undone.

"I know it's late," he said quietly with his phone still to his ear, "but can I come in?"

"Of course." I gasped when he took a step forward and wrapped me in a tight hug. My heart sank as I heard him let out a sob. I rubbed circles on his back and ran my other hand through his hair trying to calm him down.

"Do you want to talk about it?" I whispered in his ear. He nodded as he pulled away from the hug. "Come on," I said as I shut the door. I grabbed his hand and led him to the couch.

As he sat down, he started to take off his tie. "How about you get comfortable while I make some tea?" I bit my lip as he nodded. I hesitated before going to the kitchen and quickly making two cups of tea.

"Peppermint tea," I smiled as I carefully carried the two mugs back to where Winn was. "My Mom used to say that coffee is for the workaholics, but tea is for those who know better."

I sat down and handed Winn the mug. "I always liked your mom," he mumbled.

"Yeah. She was amazing," I said sadly as I thought of her.

Winn and I have know each other since we were little. In second grade, some boys were picking on me at recess. Winn saw and instantly ran over and told them to knock it off. We've been best friends ever since.

I was there for him when his mom left him. He was there for me when my parents got divorced and I had to pick sides. I was there when he went through everything with his dad. He was there when my dad became an abusive drunk. And now, whatever was going on, I was going to be here for him.

"So," I said, clearing my throat. "What's up?" I tried to sound casual to lighten the mood, but it came off sounding too forced.

"So you know how you and James have been telling me to tell Kara," he said not looking up from his mug.

"Yeah," I dragged out. My heart sank as I saw him bite his lip.

"Well it uh," he cleared his throat. "It didn't go as well as you and James thought."

"What do you mean?" I hesitated to ask.

"I may have kissed her and she immediately pulled away."