I do at least feel bad for the dead-aunt guy who might just have been a procrastinator with terrible luck. And possibly for the missed-deadling guy who might have been working on stuff but didn't get it done on time and just communicated badly. The protagonist could definitely stand to see things from other people's perspectives and be a bit more sympathetic...
...But this prospective love interest really brings it upon himself XD Okay, author, this is an... interesting place to start from, where are we going? I'm all ready to be mad at this guy, not root for a romance with him. o.o; What sort of turnabout are we heading for, hm...?