Five Teeny AU's that kinda make up one story.
1. What Tony doesn't know and something Pepper will never, ever tell him is that part of the reason she said no to being his girlfriend is because she wants so badly to say yes, her teeth hurt. She wants him to be the knight in shining armor who'll swoop in and take over her life and love her like no other. She wants him to follow through with all the promises he's not quite making and for everything to be perfect.
But she knows herself and she knows Tony (even if he's in the process of changing), and she knows that childhood dreams never, ever work.
2. He catches her looking at him sometimes. Out of the corner of his eye, or in reflections in mirrors or glass, he'll see her watching him. Not in a weird or creepy way (although, she probably deserves that honor), but with this half-wistful look that gets him half-hard and yearning for a surface to ravish her on.
He doesn't, obviously, but those little looks keep hope alive.
3. It surprises him when he falls in love with someone else. He didn't know that he could have all this unresolved whatnot for Pepper and still honestly love and adore someone else. It's confusing and hard, especially in the moments he catches Pepper off-guard, sadness written in the lines of her eyes and the curve of her mouth. Still, she said no, and actually manages to look happy for them - truly, honestly happy.
4. As sad as it sounds, it's only once Tony's in a long-term relationship that Pepper really allows herself to hit the dating scene with any kind of regularity. It actually feels good to have the time off and to spend it with men who aren't Tony. This isn't to say that seeing him with his girlfriend isn't hard, or that telling Tony she's got a date with Jeff/Brad/Andrea and watching that possessive streak of his flare up isn't fun.
It just feels like the clock is ticking on inevitability, and she needs to enjoy it while she has the chance.
5. The first time he kisses her, really kisses her, she's crying.