Hey! I just watched The Proposal (for, like, the 20th time) and decided to write a little Andrew/Margaret :D Sorry it's so short, by the way!
Disclaimer: I don't own The Proposal, the characters, or the actors! Just the idea!
The first time Andrew knew he loved Margaret was the boat incident. They had been yelling and terribly angry and just so upset and then… Then he turned around to see why the hell she wasn't fucking responding to him after she had been reckless and let go of the steering wheel and she wasn't there. She wasn't fucking there and it scared the shit out of him.
And when he saw her out there in the water and remembered she couldn't swim, he was so genuinely worried she would die that he turned that boat around right then and went back for her. After she finally got on the boat, cold and trembling and scared as hell, Andrew just gave her that sweater and held her tight and started up the 'You're fine, you're okay' chant and knew. He knew that he had feelings for her.
The next time Andrew knew he loved Margaret was at the wedding, when she was holding Gammy Annie's arm down the aisle towards him. She just looked so… Breathtaking didn't even do her justice.
Then when she confessed to the crowd about their deal and she said all those amazing things to them and him, he knew she was beautiful inside and out. It was really fucking incredible how much his opinion could change of a person after just one speech (even if he was pissed at her again after he read the letter).
The third time he knew was at the airport after stupid Chuck couldn't stop her plane and Andrew was left standing there staring after the great metal bird as it soared away, carrying the love of his life along with it.
His parents and Gammy got off the plane and his dad didn't understand what the fuck was going on at first, but after his mom had said, 'That he loves her' in response to his question, his father ambled over to apologize and give a horrible little pep-talk of some sort. But it had thrown him back into action, and that he was grateful for.
The fourth time Andrew knew he loved Margaret was when he was back in New York, after he'd ran all the way back to the office only to have her not even listen to him and show a little bit of her real, lonely self as she spoke to one of his co-workers about where to ship the boxes.
He yelled then, told her to stop speaking because he had something very important to say to her. And he proposed to her in front of that office full of people that probably still hated her and she went to say no, that he didn't want to be with her. But he wouldn't have it. He told her that yes, it may be the easier way and they stood there, staring at each other with their red, misty eyes and he knew he had to do something then, so he did. He reached forwards, framed her face with his hands, and pulled her into their very first kiss.
That was definitely not the last time, however, that he knew he loved her, but it was one of the more significant. Throughout the rest of their years, the love the two shared grew impossibly stronger and happier.
And for that… Well, for that Andrew was grateful.