First things first, if you have a good dirty joke to share don't hold out on us.

Depending on what level of friendship your aiming for, it can take between 50-340 hours to become friends with someone, according to a recent study.

[inc.com]

If you'd rather not take that much time here's a few pointers that have always worked for me. Though it's worth noting that my humor is derived very much in the moment and plays off my current conversation/scenario.

1. Pay attention. This is the foundation and should be considered to go hand in hand with all other points. Some people will make it real clear pretty quickly what their tolerance for such anecdotes is.
2. Test the waters. Start small and build to the more risque stuff slowly. Coupled with point 1 this will help you find the line fairly easily.
3. Bring it back around. Try to find a way to use their own words from an earlier point in the conversation to fuel the joke. (Point 1 will help you here.) It helps ease any potential discomfort and makes most jokes more palatable if they had a hand in helping you craft it.
4. If needed, apologize. Always be prepared to offer a sincere apology if you find that you crossed the line with this person. It may not be immediately apparent that you have done so, which is why point 1 comes back into play. Not everyone will make it plain that you've made them uncomfortable so pay attention to the aftermath and apologize accordingly.

? depends on the person...I'm not sure I tell dirty jokes really but I am certainly "inappropriate"! Like, I laugh when watching Start Trek whenever they say "sub space" ??

Depends on how involved you are with them,causal date,serious romance,College room mate,all have levels of joke telling you decide,hoping it's not too emberassing to tell the joke to.

Coming from a judgmental family I'm cautious when I first get to know someone...but after talking with them I know if they will appreciate a good old dirty joke....Its not I'm concerned with the judging, I just respect folks....no more no lesd

Depends on how funny you and your jokes are.

I usually give them at least 5mins before making an inappropriate comment, if that's well received I'll go ahead with the dirty joke if it's not well received I go in with a really dirty joke.

A few seconds. Sometimes I tell one before I even know them

The type of discourse I engage in with someone varies person to person. I'll only engage in different types of humor if I can tell they are comfortable. I try to be considerate until I'm sure the other party is comfortable, then I tend to enjoy exchanging stupid insults. My closest friends and I enjoying the insult game...lol.

Watch "The Monkey Joke" on YouTube

Usually ten minutes, then the friendship ends.

This is why I'm a hermit.

Depends. Best to use the:
SE x yAr²e Formula.
Situation/Environment x Your Ability to tell a rude joke to everyone. ?

My type of person will wait anywhere from any time before I know someone, to months after.