What is the difference between Harass and Hassle ?Feel free to just provide example sentences.

Hassle - puts up a fight (argument) but is usually not constant

Harrass - goes out of their way to constantly bother

They are very similar but "hassle" is used more in situations where Person A gives Person B a hard time. This usually happens more than once but usually isn't constant. It could be a boss who is never satisfied and makes you go back and do an assignment over and over even though you know you did it right.

Example sentence: "The boss was hassling me [giving me a hard time] for being late again."

It could be a co-worker who is argumentative and points out the flaws in your ideas or in your performance during a meeting. It could be an acquaintance who is argumentative. The term "hassle" could also be used playfully for a friend who teases you. It can be serious or good-natured depending on the circumstance, but most often it is bad.

Think of "hassle" as mental wrestling. In actual physical wrestling, sometimes a wrestler who won a fight may say about his opponent that "He really gave me a hassle". That means the victory was not easy and the loser put up a good fight.

"Harass" is much more serious. (Although "hassle can also be serious when it's your boss or a bully you accidentally bumped into on the street.) To "harass" is to bother a person constantly. "Hassle" may happen but the person doing the hassling only does so when you happen to run into each other or circumstances make you have to see each other (like in a class or meeting where ideas are presented and Person A always disagreed with Person B). But a person who is "harassing" you seeks you out constantly to seek confrontation or to humiliate you. A harasser goes out of their way to bother you.

Sexual harassment is a little different. This is when, although Person C may not go out of their way to seek out Person D, but Person D cannot avoid seeing Person C because Person D must work with Person C. Person C is constantly making unwanted sexual advances or inappropriate comments of a sexual nature. Or even if the comments are not sexual, Person C will not accept Person D's answer "No. I do not want to date you" but asks everyday and/or every time they see or run into each other. Now Person D dreads and must endure going to work without peace of mind because he/she knows he/she has to deal with Person C's behavior. This can also include the even more serious situation where Person C denies Person D a promotion unless Person D submits to sex.