Readers Assemble!

Flirting Fail (Tony Stark x fem!reader)

*Y/S/N = your sibling's name

Tony did a double take when you walked into the building. He'd certainly never seen you before. He watched as you smiled and crossed the room to where one of his employees was waving you over. He knew you didn't work there, but that really didn't bother Tony. As long as his employees were getting the work done, they could have visitors. Besides, it was lunch time anyway.

Tony straightened his tie and walked over to you and his employee. "Oh, Mr. Stark!" the employee, Y/S/N, cried when Tony approached. You turned around and smiled at Tony. Tony smirked and greeted, "Hello, gorgeous. What brings you here?" You laughed and shook your head. "Mr. Stark, this is my sister, Y/N. Y/N, my boss, Mr. Stark." You offered your hand to Tony who decided to take the charm up a notch. He took your hand in both of his and kissed the back of it.

You rolled your eyes before turning back to your sibling and saying, "Shall we? I'm starving." Y/S/N nodded and you looked back at Tony. "Pleasure to meet you, Mr. Stark." You brushed passed him, leaving Tony to stare after you wondering where he had gone wrong. Normally, when Tony Stark took the time to flirt with a woman, she swooned. Not you. You had simply chuckled at him and went on your merry way. To Tony Stark, that represented the ultimate challenge.

Tony made a point to be in the building every day at lunch for the next month. You came in at least twice a week to have lunch with Y/S/N and each time, Tony would approach you and make an attempt at flirting. Each time, you would simple chuckle, scoff or roll your eyes before leaving with Y/S/N. Tony just couldn't understand it. His charms had never failed him before and he couldn't understand why they were failing now. He had to know!

On the last day of the month, like clockwork, you wandered in with a smile on your face. You went straight to your sibling, but as you were ready to leave, Tony stopped you. "Y/N, can I talk to you for a minute?" You gave your sibling a look and then nodded to Tony. He lead you to an empty conference room and closed the door. "I gotta know. Why don't you like me? My charms are legendary and yet, you don't even comment! Why?" he questioned the moment he turned back to you.

You laughed, softly at first, but soon it grew louder until you were chuckling heartily. Tony stood there, dumbfounded. When you finally stopped laughing, there were tears in your eyes. You wiped them away and took a deep breath so you could ask, "Did you ever think maybe you were trying too hard? That you were coming on a bit too strong?" Tony opened his mouth to speak but then closed it again.

You gave his arm a reassuring pat and said, "Think about it, Mr. Stark." You left the room and met up with Y/S/N again. Tony sat in one of the chairs, brought his fingers to his lips and considered your words. Most of the women Tony flirted with immediately fell into his arms. After all, he had money, looks and great pick-up lines. He was Iron Man, for goodness sake! You were different. You had no interest in his money or his fame. You wanted something more and Tony could see that. When you returned after lunch, Tony apologized profusely, making you smile.

When Y/S/N came in the next day, Tony immediately went over. "Mr. Stark! I was going to come looking for you. My sister told me to give you this," Y/S/N said, handing over a business card. Tony read the front of the card, where your work and cell numbers were typed up. He turned it over and on the back, in neat handwriting, you had written:

How about a date, handsome? Give me a call sometime ;) -Y/N

Tony didn't even bother to hide the smile on his face.