(Disclaimer: I don't own anything, Ironman belongs to Marvel)

(A/N: This story came to me last night when I was watching "Walk The Line" I loved how John kept asking June to marry him wither he was drunk or sober, and the more I watched the more this idea formed in my head, and I thought Tony and Pepper's relationship is like Johnny and June's:) I know there's similar stories like this, especially the one from dress without sleeves but I just had to write one with Tony asking Pepper over and over again to marry him. Anyways I really hope you enjoy:)

Th first time he asks is a year before Afghanistan. He just finished working on the Hot Rod and is half drunk half sober and he looks like hell. He has grease all over him and looks like he hasn't showered or shaved in days. Pepper looks up at him when she hears him enter the living room. She's a little surprised that he wasn't out partying tonight.

"What'd you still doin' here?" He slurred his words a little but Pepper, with years of experience, has learned how to understand his drunken tone.

"I'm still cleaning out your inbox sir." she said as he sat down next to her. She could smell his aftershave and the smell of scotch and grease all mixed together on him.

"You should go home. You need rest." He said.

"I'll be done soon Mr. Stark." She said as she got busy with her--his--emails again. She didn't hear him move or say anything else but when a hand came over her laptop to shut the lid she jumped a little.

"No. You need rest now." He said as he took her laptop and settled it down on the coffee table.

"Fine. But I need to get you cleaned up first." She said as she helped him to his feet and put an arm around him to guide him upstairs. Then he said something that took her completely by surprise...

"We should get married. I know this great Casino Hall in Vega's." He said with a smile. She didn't say anything, not really knowing what to say when her half drunk boss just asked if they wanted to get married in Vega's. By the time they reached his bedroom he was just about passed out.

"So what'd ya say Pepper?" He asked with a grin as she laid him down on his bed.

"...Good night Mr. Stark."

The next time he asks her is when she's patching him up after an Iron Man mission. She doesn't really notice he's staring at her, she's more focused on the big swelling bruise on his shoulder.

"Hey Potts, how come you're not married?" He asked. Once again she was taken back by the sudden, random question.

"Um..I'm sorry what?" She asked confused.

"Why aren't you married? Why don't you get married?" He asked again.

"...Because I'm to busy running your life." She said as she put some ice on his shoulder, he hissed in pain and got on his feet as she rubbed peroxide on his back.

"But that shouldn't stop you from dating and marring your boss." He said with a smile even though he knows she can't see it.

"Excuse me?" She asked as she arched an eye brow.

"Well just because you run my life shouldn't stop you from wanting to marry your handsome, devilish boss." He said with a really big grin now. She huffed out a breath and put the peroxide and gauze pads away and retreated up stairs while hearing her handsome, devilish boss snickering.

The third time he asks her is when he's sick and can't get out of bed. Pepper's standing above him taking his temperature while Tony is looking worse than he ever has.

"103.7. That's it Mr. Stark, no going down to your work shop today." Pepper said as she cleaned the thermometer and put it away.

"I don't even think I could make it down there by myself...unless you were going to help me?" He asked and still amazed her that as sick as he is, he can still crack a joke, one she wasn't taking today.

"No Mr. Stark. You are to stay in bed until you get better. No going down to the work shop to work on the suit or your cars. No going into the office today. And NO missions until you get better. Clear?" She asked sternly. All Tony did was give her a cheecky grin and...

"Well if we were married I'd probably would remember more." He said with humor, even though he knew Pepper was in no mood for it today.

"If we were married I would find very painful ways to make you remember." She said as she pursed her lips, something Tony found very attractive.

"Does that mean you'll marry me?" He said with a bigger grin.

"No Mr. Stark. I'm far to busy." She said as she propped a pillow behind his head and walked out the door and cracking it.

"Love you too!" Tony yelled back, and she heard those words repeat in her head all day long.

The forth time was a few weeks after he told the world he was Iron Man and the work just piled on for poor Pepper Potts.

She was walking down the stairs to his work shop, completely stressed and not even watching where she was going, just to busy focusing on going to her apartment and get some sleep. She was so tired that she miss calculated the step count as she walked down to his work shop and ended up skipping a few steps and falling into some of glass that had yet to be picked up from the doors. Tony heard this and ran as fast as he could over to her. She had some glass stuck in her arm but she mostly was still in the stair way.

"Pepper are you okay?" Tony asked frantically as he helped her up.

"Um..yeah, I just have some glass in my arm." She said as she lifted her right arm to show several pieces of glass in her arm and hand.

"Come on, I'll get the first aid kit." Tony said as he helped her over to the chair where she had to change his Arc Reactor that one time. She still shuddered at the memory but sat down when Tony got the tweezers out of the first aid kit.

"Ow!" She yelped as he started taking the glass out.

"Sorry. So...what happened? How did you fall Potts?" He asked.

"..I, I guess I was just to tired and not thinking clearly when I was walking down here." She said.

"Too tired from working for an annoying man like me?" He asked with a laugh.

"You could say that, Iron Man." She hissed out the last part.

"I'm sorry about that. Are you going to sue me for injury-on-the-job?" He said with another chuckle.

"Maybe...I have been eyeing these new shoes I've seen at the mall." She teased.

"Well, you know, when we get married you won't need a law sue just to get a pair of shoes." He said with a grin. She sighed and rolled her eyes.

"Right. Of course Mr. Stark." She said sarcastically.

"You know, I always take what you say seriously Miss Potts." He said with a big grin as he removed the last piece of glass.

"I'm sure you do Mr. Stark." She leaned into him and kissed his cheek. "Thank you Mr. Stark."

"Your welcome Miss Potts."

The Fifth and final time he asks Pepper she was once again sitting in the living room of her boss's mansion and it was well after mid night and way past when her shift ended. She didn't hear Tony come up from his garage/work shop.

"Wow, another all-nighter Potts?" He asked with amusement.

"Yes Mr. Stark. I still have at least 500 emails left to sort out before I can go home." She said, still not looking up at him from her laptop. She, again, did not notice him sit down next to her but she did give another yelp as he closed her laptop.

"No. You need rest." He said as he guided her to her feet.

"Tony I--"

"No, whatever it is it can wait until tomorrow Pepper." He said sternly but yet softly. He took her to one of the guest bedrooms.

"Tony I can go home and sleep in my own bed." She said.

"Yeah but you look exhausted and your apartment is a 30 minute car drive from here. It's safer to just spend the night, and away from your laptop as far as you can be." He added with a genuine smile. Pepper gave in and sat down on the guest bed while taking her shoes off. The light came on automatically when they entered and Tony was resting his head against the door way.

"Yes...?" She asked. She noticed that he seemed like he wanted to ask her something. He bit his lip nervously before kneeling next to her bed, and she really had no clue this time what he was about to do.

"...Pepper...marry me." He says as he pulled out a black velvet box. Pepper's mouth hung wide at this. Sure he's asked her that before but only as a joke. He has never got down on one knee and asked so seriously. She would have laughed and said "You got me" but the look in his eyes said it all, 'I love you Pepper'. Tony was starting to get real nervous and his palms were starting to sweat a little. Pepper smiled down at him and nodded her head. She dropped down next to Tony and kissed him.

"Yes, I will Tony"

Well i hope you guys liked it. This story was so much fun writing. Please review:)