The Principal (To Love-Ru)

An unnamed principal is a minor yet recurring character of the harem manga series, To Love-Ru

Why He's Loathsome:

 * 1) He is a rip off of Herbert the Pervert, and Glenn Quagmire from Family Guy. Just like them, he feels more like a Family Guy character than a minor harem character.
 * 2) He may be middle aged, but he is downright annoying.
 * 3) Despite being unlikeable, he gets a lot of screen-time.
 * 4) Despite he lured girls in school, he doesn't get punished nor gets fired.