What's the difference between a clown and a jerk; where's your "fine line" between amusing and annoying?

I’d say Louis C.K. does a pretty solid job straddling that line.

… there’s a fine, fine line between what you wanted and what you got. (from this song)

There’s a story I tell my students: If you have a big pot of hot water, and accidentally trip and spill it on your best friend… most likely your friend will have forgiven you before your first “sorry” bursts out. On the other hand, if you have a tall glass of cool water and accidentally trip and spill it on an enemy, you can bet they’ll work really hard at ripping you a new one and won’t stop until they are satisfied.

So a jerk and a clown, in my opinion, differ only in whether the person observing finds them to be cute and darling, or worthy of being squashed by a flyswatter. The song is not completely relevant, but I couldn’t resist the allusion using that one line.

I think clowns are merely foolish and silly (and can be slightly annoying or extremely exasperating) but deep down they have a good heart and are really not trying to hurt anyone and would probably cut out the crap if you asked them to, especially if you gave them some polite reasons why it would be best if they refrained from all the jokiness. Sometimes these folks don’t realize that there is a time and a place for jokiness and you may have to explain the nuances to them. Although some poor clowns are just not intelligent enough to realize how annoying they are (for a whole host of reasons) Those types of clowns are to be pitied (and some times you have to avoid them if you just can’t take it and they don’t understand your hints to cool it).

A jerk, on the other hand can also be foolish and silly, but they are also likely to be very selfish and mean and not give a darn if they are hurting somebody’s feelings. Their actions don’t come from an altruistic place, they come from a self-centered place. These types of folks tend to get a charge out of insulting and/or hurting other people. The scariest thing about them is that they often appear to be funny or charming in the first place (that’s how they draw you in) and then they turn into self-serving mean jerks. They are often manipulative and controlling. Avoid having one of these folks as a boss or a spouse.

Number 1: timing. Number 2: taste. Number 3: your audience. And you’ve either got it or you don’t. If you’re feeling insecure, back off and see what the reaction of your usual audience is.
For example, if you’re telling a joke and you get interrupted, don’t tell the rest of it unless there is a request. You may enjoy telling it more than your audience want’s to listen. It may make you disappointed, but it will be a true test.

^ For example, if you’re telling a joke and you get interrupted, don’t tell the rest of it unless there is a request. You may enjoy telling it more than your audience want’s to listen. It may make you disappointed, but it will be a true test.

Interesting.