You/Angelina Jolie - Babysitter

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Summary: You've been her babysitter for a while

Prompt by: MerlucasMind 

Angelina had hired you right as you had gotten out of college. Time's were though and you literally applied for any job that was available. The only reason why you were even able to get it was because you knew someone that was well connected to the stars and heard about Angelina and Brad needing a babysitter. 

You were hired right away and had moved in the week that all the paperwork had been signed. It was honestly quite surprising that you would be earning that much just for taking care of their kids while they were away. It wasn't too bad considering they had both taken jobs that were close to their home. 

Overall, your experience while working with them was quite amazing. Both of them were great bosses. They allowed you time off that you requested and even helped you out on certain things you were struggling. Brad would hardly ever be around but he did help out whenever you needed him. Angelina was the one that you saw practically every day. You were at first hesitant about the fact that you were talking to your boss like if she was your friend but you ended up warming up to her. 

Everything was going fine. You got along with the kids, the pay was great and you got a lot of vacation dates. That is until you slowly started to develop feelings for your boss, Angelina. You couldn't help it. It was the little things she would do that attracted you and it was terrible. She kept doing them and all you could do was smile and thank her. It sucked how useless you tended to get whenever you were around someone that you liked, especially if they were married. 


Babysitting for Angelina had meant to just be a temporary thing. It was only suppose to last until Angelina finished her film but they decided to extend your contract. Practically telling you that they'll be giving you a job until you decided to leave. To which you wouldn't. Why would anyone leave a job that paid so much, had great bosses and lots of vacation. 

You've been there for a total of 3 years. Lots of things had happened but the thing that you couldn't help but be overjoyed was the fact that Brad and Angelina had divorced. You felt incredibly bad for saying it but it was the truth. Perhaps, you would have the tiniest chance on being able to date her. 


"How come you never mention a boyfriend or girlfriend?"

Angie asked you out of the blue as the two of you had dropped of her kids at a birthday sleepover. 

"I'm not really interested in anyone. Plus this job is full-time and I don't have time for anything meaningless."

Angelina stared at you for the longest time. She looked like she was contemplating something but before she could ask, she turned to face the road and headed back to her place. 

"It's bull."

"I'm sorry."

You weren't surprised at her words but more about how she had brought it up again.

"That you're using this job as an excuse to not go out and date anyone. Also the fact that you don't like anyone."

"It's the truth. I don't like anyone and I'm not using this job as an excuse it's the truth."

"Then go out with me."

You started laughing, practically in tears as you heard her. She wasn't serious, was she? You forced yourself to take a breather and looked up to find Angelina with an amused smile. 

"I'm serious. I like you, (y/n). You said you're not interested in anyone at the moment and you won't be able to use your job as an excuse this time because you would literally be going out with your boss."

Your heart started racing. It wasn't like you had imagined her asking you out but it was quite close. 

"I promise to give you the time of your life. I'll get another babysitter for the night and see how the night turns out. What do you think."

Angelina was getting worried, she had thought you would have jumped at the chance of going out on a date but she was wrong. You currently looked like you wanted to flee. She couldn't be any more wrong.

"I'm sorry. I shouldn't have asked. God, is this inappropriate? What was I thi-"

"Yes. I would love to go out on a date with you."

You decided to interrupt not wanting to make her feel bad.

Angie surprises you and gives you a kiss. 

"I'm sorry, I couldn't wait for the first date."

"Me neither. Now kiss me again."

She led you inside the house where the two of you skipped the second and third date as well. 


Send me prompts and suggestions. Will do any female celebrity or character.

I have several prompts to do and will post them in this order

Lena Luthor/Kara Danvers

Cat Grant

Lena Luthor

Angelina Jolie

Scarlett Johanson

Maggie, Lena, Alex, Kara

Alex Morgan - Part 2

Daenerys, Cersei, Sansa, and Arya - Part 2

Walking Dead


Sorry for the long wait. Will try to post them as soon as I can.

Thank you!

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