To be fair to 2 on the list:
-Hyodo Issei suffers from PTSD since the first girl who showed interest in him , was the one who killed him, he’s got a bit to work through
-as far as Kyosuke from Oreimo is concerned. Kuroneko is more to blame for him hooking up with Kirino, since she broke up with him in the Shittiest way possible, then expected him to choose her
(please excuse the language)