Filmmaker Kevin Lim tells the story of Shilo Dashwood, a self-made woman who drinks as hard and she works. Every Wednesday, she meets with her long-suffering personal assistant Teddy to conduct matters of business.
But today, he’s interrupted by a text from his girlfriend Audrey. He pauses before revealing that he broke a promise with her to work late. Shilo remembers Audrey, affectionately calling her “goat-face.”
Shilo pushes ahead and keeps insulting Teddy, even insinuating that he may be gay. Finally, Teddy reveals that Audrey broke up with him because she thinks he and Shilo are having an affair.
Shilo offers to help fix the situation, but Teddy refuses — insisting that every time he shares something personal with her, she drunkenly ridicules him and forgets about it the next day.
For a moment, Shilo becomes serious. Then, she reveals all the important events of Teddy’s life that he assumed she never noticed. He’s surprised.
Teddy then asks Shilo if she’s ever loved someone.
For a brief, vulnerable moment, she opens up an old wound from her past — about a man she could never win the affections of. As she tells the story, she sheds her armor and shows she wasn’t always a cynical pragmatist — she once felt heartache, as well.
Shilo and Teddy quickly exchange gifts — small show of sacrifice. Then, they mull over the co-dependency they’ve come to rely on each other for.
That’s when they both agree to make a change.