When he looks back it's hard to know when his feelings for her changed. When she went from his cutesy young friend to everything he ever wanted.
He knows that even casual onlookers have seen this coming a mile off; seen the ridiculous excuses they come up with to spend time together and the opportunities he jumps at to touch her in even the most infinitesimal ways. Abed tells him he knows the exact moment, but for the sake of the romantic narrative he chooses not to share it.
There were those kisses, for one thing. The debate team finale that ignited feelings he'd never even let himself consider before. Or their moment at the end of first year; when he'd kissed her until his lips were sore and let himself relish the feel of her, small but determined in his arms.
If he had to pick one moment himself, just one second where he first realised that he was teetering on the edge of something more than just slightly creepy lust, it would be the night she came over to find him drunk and cycling through his collection of sad childhood memorabilia. He let her wipe away the tears on his cheeks with the pads of her thumbs, make him soup and wrap them both in a blanket on his sofa. If it was anyone else they might have laughed at him, fully grown and still clinging to mementos of a father he claimed meant nothing to him. Annie just let him be with his grief.
She came back the next night with an arm full of craft supplies; he stared at her in horror as she unloaded sequins, ribbon and construction paper on to his coffee table.
"Annie, what the hell is this?"
"Crafting is cathartic," she said simply, as if that explained everything, "We're going to make a scrapbook!"
"A what now?"
"A scrapbook. We're going to put all of these things together in a nice book so you don't have to keep being ashamed of them."
He was still dubious when he sat down on the floor next to her, slumped over the coffee table and sorted through the page options.
"If I do this will you promise to never mention it to the others?"
She looked at him as if he were stating the obvious and his stomach at flipped at those doe eyes of hers; the look of concentration on her face as she carefully pasted his most guarded memories in to something beautiful.
And so now, when he's still reeling that she's agreed to move in with him, he finds himself enthusiastically agreeing with the minute changes she makes to his apartment. The photo collages that hang up next to the art he purchased at Target; the home-made cookies that sit on a plate in his previously carb-free fridge; the ridiculous throw pillows showing off her brief foray in to cross stitch.
He loves her a little more for every time she takes a piece of his life and turns it in to something, in her very Annie way, infinitely beautiful.