Bill Hader Imagines

Why Are You Crying? (Richie Tozier)

Y/N had been Richie's assistant for two years, and she loved every minute of it. Richie was fun to work with and, he always managed to make her laugh with stupid jokes. The only downside was that Y/N had been harboring feelings for him.

She hid her feelings from him and just focused on helping him write new material for his show. Together, they came up with the funniest jokes and punch lines, and Y/N super happy to be working with a comedy genius.

Tonight was Richie's last show of his tour. He and Y/N had wrote down new jokes for the past two hours, and now, Richie had to get dressed in his onstage attire.

Y/N stood outside his dressing room with a bottle of water for him to sip on before he went onstage. The dressing room door opened, and Y/N forced her jaw not to drop. He looked absolutely amazing in his suit as always.

Y/N walked with Richie to his entrance to the stage. Richie turned towards her and gave her a nervous smile. His hands began to shake a bit, but Y/N automatically reached out and grabbed them.

"Hey, Rich. You're okay. This is your last show, and I know that you're gonna knock them dead."
"Thanks, Y/N. I needed a little pep talk, and I'm glad it came from you."
"No problem. That's what I'm here for."

Y/N was caught off guard as Richie pulled her into a tight hug. She hugged him back and attempted to hide the blush that was spreading to her cheeks. Richie pulled back as he heard the announcer say his name.

"Good luck, Richie."

Y/N spoke with a huge smile on her face. Richie smiled back at her, then turned and walked out on stage. The audience began cheering and clapping as he took his place on stage.

Y/N watched Richie from the side of the stage. She smiled to herself as she watched the man she was falling for do his thing on stage. Richie told one her jokes, and he looked towards her, shooting her a playful wink.

She began to think about Richie, and how he made her feel. They might not have been together, but he still had an effect on her. Y/N's feelings began to rise, and she ran from the side of the stage, looking for somewhere to hide herself backstage. 

She had began crying, and she didn't hear that the show had ended. She heard someone walk around the corner, and she tried her best to hide her cries. It didn't work because the person found her immediately.

Y/N looked up and saw Richie standing over her. He slowly crouched down and placed a hand on her knee.

"Y/N, are you okay? Why are you crying?"
"Y-Yeah, I'm fine, Richie."

More tears began to fill Y/N's eyes as she attempted to lie to Richie. He didn't buy it though.

"You're clearly not okay. Come on."

He suddenly stood up and grabbed YN's hands, pulling her up with him. He lead them to his dressing room and closed the door once they were inside.

Richie lead Y/N over to the couch, and they both sat down. He stared at Y/N, dying to know what was bothering her.

"What's wrong, Y/N. You can tell me."

Y/N sighed and looked at Richie to find him already looking at her. She took a deep breath and tired to find the right words to say.

"S-So, I've worked with you for a little over two years, and within these past two year, I have developed strong feeling for you, and I've tried to get rid of them, but I can't. I know that you're technically my boss, and I totally understand if you don't feel the same way-"

Y/N was interrupted by Richie pressing his lips against hers. She was shocked at first, but she eased into the kiss, wrapping her arms around his neck. When air became necessary, they both pulled away and looked at each other.

"What was that for?"
"I couldn't think of any other way to shut you up so I could speak."

Y/N gave him a look that was begging for him to continue speaking. He grabbed her hands and looked deeply into her eyes.

"I have feelings for you too, and I didn't say anything because I'm your boss, and I didn't want you to take it the wrong way."
"R-Really? Why?"
"Because you're absolutely amazing. You're super funny and stunningly beautiful, and a guy like me doesn't deserve to be with someone like you."

Y/N pulled Richie into a hug, and he instantly wrapped his arms around her waist, pulling her closer to him. He leaned back and placed a kiss on her forehead. She smiled at him, and he smiled right back at her.

Although Richie didn't think he deserved to be with someone like Y/N, he wasn't letting her go now. He finally had the one person that brought happiness to his life.