AN: Hi everyone! This is going to be a series of short moments coming from the scene at the end of 'Spider-Man: Homecoming' when Tony proposes to Pepper and Happy claims to have been carrying the ring around since 2008, and, as expected, none of it belongs to me. The chapters are all short, but because each one jumps forward quite a bit in time I felt it worked better for each to get a chapter of its own. The title of each chapter is the month and year in which it takes place, but I know there's a lot of dispute over dates and timelines in the MCU so for clarity I will put an AN for each one to explain when it occurs relative to the films.

This chapter is set before the beginning of 'Iron Man'.

Enjoy :)

November 2008

"Just lift your feet off the ground a bit more, boss, almost there" Happy Hogan grunted, oblivious to the beauty of the sunrise as he hauled his employer towards the mansion.

"Happy, Haaaappy, listen t'me, I need you t'do somethin' for me." Tony slurred as they reached the door.

"I'm already doing it – I'm getting you home." Happy shot back, straining to reach his pocket without dropping Tony. "JARVIS open the door, could you?"

"Certainly, sir." came the reply as the door swung open.

With new found enthusiasm Happy dragged Tony across the room and deposited him on the sofa.

"Right - night, boss!" he called, already making his way out again.

"Happy waaaait! I still need you to do the thing for me!"

Rubbing a hand over his groggy eyes, he turned back to face his employer.

"I need you to keep it secret though! It is of the extremestest importance than no people find out about this 'cept for you."

Happy nodded, internally counting how many hours sleep he could get before he had to collect Miss Potts for work while Tony fumbled about in the pockets of his rumpled suit jacket. Eventually he produced a small, velvet box and held it up for Happy to see.

"No! Tony, tell me you didn't!" he exclaimed, shaking out of his stupor. "This'll be a nightmare for Miss Potts to sort!"

"Nooooooo, Hogan, you misinterpertate. Pepper'll love it." Tony grinned, waving the box around in his hand.

"I really don't think she will, boss. How public was it? How much do the media know?"

"Course she'll love it, it'll suit her perfectly." Tony mumbled sappily as he opened the box to admire the ring inside.

Happy stood for a moment, unsure if his tired brain had heard Tony's words correctly. Suddenly Tony was standing a few feet from him, narrowly avoiding Happy's nose as he waved the box in front of his face.

"I need you to mind it for a bit." he said, looking suddenly much more sober than he had been before. "Just 'til I get a few things sorted out."

"Okaaaay," Happy replied, watching Tony suspiciously, "Look I'm far too tired for your games, Tony, I want to go to sleep and you should too."

"I'm not playin' any games here. I need you to keep a hold of it, just for a few years or so, so when I talk Pepper round to it she can marry me."

"And that's going to happen?" he asked, raising an eyebrow.

"Course it is. Just not just yet. Which is WHY I need you to look after it. And then when I need it I'll know where it is."

Tony was giving his best sincere puppy eyes, but it was the thought of his soft bed at home that won Happy over.

"If I take it can I leave?" He asked sullenly.

"Absolutely."

"Fine." he said, grabbing the tiny box and storming towards the door. "But I hope you're thoroughly embarrassed about this in the morning."

"I won't be." Tony called cheerfully as Happy shut the door.

"You're right, it'll be the afternoon."