Ichigo Kurosaki

•Honestly, it might not be as difficult of a process as you might think. At least not at first. He’ll have a lot of ideas in his head, but once he starts eliminating options and considering whether or not they sound silly or boring, it comes down to the final few, and that’s when he might panic a little

•He’d probably lean more toward a chill date, rather than a super romantic one (at least for the first date). It’s closer to the atmosphere he feels most comfortable in, and he’d want his date to loosen up around him and feel just as comfortable

•That in mind, he’d also make the actual asking out part very casual. Whether it’s just a short talk by their locker at school, offering to walk them home and then asking, or, and this might border a little too cowardly for him, he might ask one of their friends to mention it to the person first, just so Ichigo could test the waters. But I think he’s more of direct guy, so he wouldn’t resort to that unless he was like, super intimidated by the person

•It’s possible that he could stutter and mess up, highly possible. But when he’s smooth, it’s pretty good. He passes it off with something like “If you’re not doing anything tomorrow night…” or “Do you think you’d be down for _______ a little later?” Would never actually use the word date, but he’d be pretty forward with his intentions and tell them exactly what he had planned

•However, he can be the type who asks them to choose where they want to go. He knows it can be troublesome and most people like the dates to be planned, but sometimes he just worries that he’ll pick somewhere boring? Or somewhere they don’t like in particular? Better to be safe than sorry