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Oliver Warbucks was a cold, ever-working man.
Yeah, not anymore.
And here's a few examples of times their new bond was truly being shown or tested.
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Now that Oliver has Annie running around the place, his whole world's been changed in a lot of ways that he didn't expect. Like the fact that all of his staff decided to team up and adopt the several other orphans left at the orphanage for Christmas, which was great in theory, until he thought about the fact that all of his staff lived in a wing of his estate. Seven little girls always running about was a handful at least, but Oliver was trying his hardest.
"Daddy Warbucks?" Annie asked one afternoon, snapping Oliver out of his thoughts. "What is it dear, you know I'm working at the moment-" "Molly got sick on the floor... Cecile is taking care of it, but I thought I'd tell you, I'm not ever really sure why." Just wonderful he thought. He never was quite a fan of dirt and grime, let alone vomit, but the fact she was willing to tell him something random out of the blue gave him a soft feeling in his heart.
"How about you stay in here till it's cleaned up? I suppose a break wouldn't be too bad on me; I've been working all morning." Annie's smile seemed to light up his whole office with how bright it was. Annie was pleased with such an answer, going to his shelf drawer and opening it, pulling out a checkers set. He's used to this by now, but every time they play together always brings a spark to his face. "Of course we can play, just don't expect me to go easy on you, dear."
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Oliver was stuck in his bed all day, and for the first time since he's adopted Annie, he's having a genuinely bad day. Today would have been his 40th wedding anniversary with his dear Edith, and her passing has always made this day a hard day for him. Edith passed twenty-five years prior due to childbirth complications, and that fact stayed with him for a long time. He thought it was his fault for her death, even though he's heard plenty that it isn't true.
He glances at a framed picture of their wedding all those years ago, her smiling face, her soft brown eyes, her light brown princess curls tucked into a bun. She was a bigger woman, but he didn't mind at all, he loved every bit of her with his whole heart. That's why it's so painful now, decades later, as he looks upon what was such a cheerful picture, it's memory forever tainted with macabre sadness.
He hears his bedroom door creak open, Annie's head of ginger curls peaking in. "Daddy Warbucks? You've been in here all day... are you alright?" Oliver changed his gaze to focus on her, a slight smile coming to his face. "Not truly, but you made it a lot better stopping by. Care to hear a story?" Annie's interest was piqued at the mention of a story, so she fully entered the room, climbing onto the bed with him. "I have one I think you'll enjoy hearing..."
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Oliver was sitting by the pool, watching his staff, their children and Annie having a good time from his deck chair. "Grace?" "Yes, sir?" She replied from the deck chair beside him, lifting her sunglasses up. "Please Grace, just call me Oliver, no need for formality at this event. But I must ask... what is Drake doing?"
Grace looked over at Drake, whose inflatable raft was being capsized as the girls tried to climb atop him. "Oh my goodness, oh my goodness!" Tessie said as her head peaked up above the water, her shoulder length curls wet, making her look more like a wet dog as Molly and Duffy swam away giggling. Kate and July were splashing each other as they came back up from under the water's surface as Pepper was calling them all a bunch of dumbbells from the poolside for messing with her new father. The scene was wholesome in a new chaotic way.
Oliver wishes his dear Edith could be there beside him and see how much he's grown. Be the mother of his little girl, who is now his whole world just like she was before. But maybe this is for the better. Edith wouldn't have wanted him to be in misery, especially on such a lovely day, and Oliver knows in his heart she would have loved Annie just as much as he does.
"Were you even listening to what I said? ...You're getting in your head again, Oliver. How about you go join them? Live a little, you deserve it." Were Grace's only words. And Oliver decided to take them.