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There are some things I've never properly established for my cast - I don't have their blood types or their birthdays or a list of everyone's favourite foods. This is for two reasons: on one hand, it's far too much work for something that doesn't matter to the story, and on the other hand, leaving it unstated allows me to insert something specific later if a plotline requires it.

One of the things I could specify but haven't is all the cisfemale characters' menstrual cycles. Leftover Soup does have a specific timeline - if I wanted to, I could easily make a little day chart and line up everyone's uterine schedules on it. "Okay, this is the third week, so in this scene, Gina is just starting her period and Nicole is just ending, I'd better be sure to let that information inform their mood and dialogue in this conversation about fourth edition D&D rules..."

I'm not going to do that - not for my work, nor for any other work of fiction. It would be creepy as fuck.

As I've stated before, creepiness is in the eye of the beholder. Jamie's specific behaviour here is only creepy insofar as Ellen had not expected it. Certainly he hadn't intended to be unnerving or inappropriate. He just happens to be observant about the wrong things - as Ellen said: low Wis, but points in Spot.

(Sunday night, INT: EB and JH's apartment)

EB: I think maybe accepting that you'll never be a complete adult is part of being a complete adult. Understanding that everyone else who appears to have their shit together is just as much a jumbled mess behind a mask as you are.
JH: ...or maybe that's what jumbled messes behind masks tell themselves.
EB: Whatever. Fuck it. No waiting until we're ready. Jamie, do you want to go on a date with me?
JH: I don't think we need to go on a date, do we? I mean, if the point of a date is assessing a potential romantic partner... we already know each other. We've lived together, we've eaten together, we've played games together, I know when your menstrual cycle is...
EB: Why do you know when my menstrual cycle is?
JH: Because I take out the bathroom trash and I can do basic math.
EB: That is unfathomably creepy.
JH: How is that creepy? I'm showing an interest in you and your wellbeing.
JH: Oh, speaking of, I got you a refill of that cream for your armpit rash.
EB: Great. Thanks. Super glad you did that.
JH: See? Not creepy. Helpful.
EB: Right.