Bill Hader Imagines

You're A Beautiful Woman (Bill Hader)

(I recommend watching the video first!!😁)

Y/N considered herself lucky to have the opportunity to work on Documentary Now as a writer. She had known Bill, Fred, and Seth since their SNL days, and she was so happy that they asked her to work on the show.

She had a huge crush on Bill, but she was too afraid to tell him how she felt. Instead, she decided to crack jokes and make fun of each other and their friends.

On the first day of filming 'Sandy Passage', Y/N walked onto set, looking for Bill. A PA pointed her in the direction of hair and makeup, and Y/N made her way there. When she approached the hair and makeup located, she saw Bill standing in front of full length mirror fixing his wardrobe. She let out a huge snort when she saw his outfit. He quickly turned around and saw her standing there.

"My, my, my, Bill. I must say that you're a beautiful woman. This outfit really works on you. Those are some mice legs you got there."

Y/N barely got her last sentence out without laughing. Bill had a look in his face, and Y/N shot him her award winning smile. He shook his head and laughed.

"If you think this is funny, wait till you see the first scene were filming. You're gonna lose it."
"Oh, now I'm excited. What scene is being shot first?"
"The scene were I dance right in front of the camera."
"Today is gonna be a great day."

Bill and Y/N continues to talk, and Seth and Fred watched them from a distance. They knew that Y/N and Bill had a thing for each other, but neither of them wanted to make the first move. They just watched as their friends tried to make their feelings seem invisible. The director called Bill and the others to the set, and they began filming the scene. Bill tripped a couple times on the steps making everyone laugh.

The director called cut on the scene, and Bill walked over to the wardrobe location to get into his next outfit. Y/N followed him, and they talked and laughed some more.

"Those were some good moves, Hader. This show is gonna be fucking amazing. I already know it."
"Yeah, its gonna be great."
"Well, I better go so you can change."

Y/N turned to walk away, but she stopped when she felt Bill grab her wrist. She turned back to face him, and he had a nervous look on his face.

"Yeah, Bill?"
"Um...I was wondering if you would maybe like to go out with me sometime? Like not as friend, like an actual date."

A shocked expression came to Y/N's face, and Bill took it as a bad sign. He stepped back away from her and let out a nervous chuckle.

"You can say no if you want too. I would totally understand if you didn't want to-"
"I'd love to go out with you, Bill."
"Wait, really?"
"Yeah, I've actually had a crush on you for a while, but I was to afraid to say anything."
"I've liked you for awhile too. How's Friday night sound?"
"It's perfect."

Y/N leaned towards him and placed a sweet kiss on his cheek. She heard someone yell for her, and she smiled at him.

"Well, I gotta go. Duty calls."

As soon as Y/N turned her back towards Bill to walk away, he began silently celebrating. He was so happy that she said yes. He knew that this was the start of something new, and he was excited to see where their journey would lead them.