Hc prompt;; Whats a date with Miles typically look like/Consist of?
headcanon | always accepting
This goes in one of three categories because Miles is greyromantic, so he very very rarely ever develops romantic feelings for anyone and thus doesn't feel the need to 'date' in the classical sense. (He does share very deep connections with everyone he cares about, however this is a topic for another time.)
One, most likely: it's just hooking up. He's a very sexual person and he knows he's pretty — it usually doesn't take him much effort to pick someone up to take home; although it usually stays at one night stands. Here's a thing: Miles will either obsess over someone in one way or another (not all of them positive), or lose interest almost immediately. It highly depends on how interesting he finds someone.
Secondly, and in a similar vein — using people. Again, he's aware he's pretty and charming, and the easiest way to get people to open up about things they shouldn't is usually to feign interest into them or sleeping with them so that also means occasionally going out with people he has no real interest in; but at the end of the day he's still there to dig up dirt on people and will use whatever means possible to achieve such. Naturally that means he'll adapt to whatever his chosen victim wants him to be in such a situation, it's simply an act to get what he wants.
Third, rarest, when he actually does care about someone — he really wants to impress people. He'll be way early, then nervously pacing. If given the opportunity he will absolutely cook for the other person because it's something he's both passionate about and knows he's good at — going out is fine and all, but when he's actually into his partner he will want to make it somewhat private and personal. If going out is a thing, he'll try to find something oddly specific that aligns with their interests — if they mentioned they liked reading, he'll take them to a small hidden bookstore and make a game out of reading passages to each other; if they have an interest in architecture he's going to figure out how to sneakily get them to gorgeous sights that aren't actually accessible to the public (although being a journalist helps there), or taking them to the arcade with unique challenges or a board game cafe, or even something stupid like making a game out who can make the most dumb puns about a certain topic. Go to an art gallery and pretend to know shit about art, making a whole lecture up on scratch. He tries to be creative.
He's very attentive then. Not that he isn't generally about people he cares about, but in such situations they really become the sole focus of his attention, which can be ... a little intense, sometimes.
