jester from fate strange fake... but also i think that you might like addelle from baccano

Raynesia from Log Horizon. She's a bit outside your usual tropes, but a young woman choosing to go from a political pawn of her grandfather's to a player on the board, using her looks to get a large group of adventurers to actively participate in a large battle against goblins...I can see that.

(Though Akatsuki might also be an option. Deadly ninja, fiercely into roleplaying, pining over the nerdy guy...)

i'm not sure about anyone in macross delta specifically, but i think you'd like grace o'connor from the prev entry (macross frontier), who is very much a girlboss

knives I think

encouraging asha and/or arya

timekeeper cookie.... girlboss who isn't afraid to fuck around

i stg I haven't suggested a single character whose series I've actually played from once tonight, but klaasje discoelysium, maybe?

odasaku: oh i looked her up and shes hot

i have an oc named jester who is a vampire lad so jester fate strange fake vexes me every day

darkersolstice: akatsuki seems very gender too

subwaymaster: oh i looked her up and her design is very good.... the idea of a galaxy conquering idol manager is very fun to me

goodluckmodes: yeah he fits. anime boy chara.

bitterends: i do need to set up an arya journal

spellweaver: this cookie isn't here to make friends