I headcanon when Whitaker first moved in with Santos he just kinda kept to himself
At first he kept all his stuff in his bag, then he slowly started leaving stuff on his bed. He didn't put anything in the closet; he felt it just looked pathetic with two shirts and a few pairs of old jeans from his farm days.
He would wait until Santos was done in the kitchen to make his coffee, and wouldn't use creamer or anything because he felt bad thinking about how it costs money to replace.
Santos and Whitaker might grunt or nod heads at eachother but that's about it.
Until one night, Santos is in the living room watching some movie and Whitaker comes in to make coffee and gets hooked, standing in the kitchen trying to discreetly see how it ends.
Santos knows he never left, and she doesn't really care, but about after ten minutes it gets a bit uncomfortable knowing he's just standing behind her in the dark.
Eventually, Dennis hears a "Are you gonna sit down or what?"
"I really don't care. And you can use the creamer, dude, I'm not gonna kill you."
At his pitiful expression, she adds, "I'm just joking, Fuckleberry. Are we gonna do this all night or can I focus on [insert hot woman in said movie here]?"
And they spend the rest of the evening watching that movie together.
The next morning when Dennis walks in, he hears a "hey".
The next week, while Dennis is lying in bed, Trinity walks in and promptly throws a fuck ton of shirts at his face.
Once he's pried enough of the clothes from his face that he can actually see, he goes, "huh?"
"I don't wear these anymore. Thought you might like a shirt from somewhere other than 'Broken Brow High'," and then she's gone.
Dennis never brings up the price tag he found dangling inside one of the shirts.
She never brings up the fact she sees him wear it every other night.
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