Using colloquial language is fine in everyday conversation, but avoid using too much slang or too many vulgarities in your speech unless you share that with your trusted person. Don't put up with bullying or think of it as a meaningful conversation even if the bully says it is.
Don't think that a long detailed conversation about everything that's wrong with you is deep or meaningful unless its content is genuinely constructive critique. If you value time, aim at productivity and contribution, you would want to maximize your conversation to end up being a meaningful. Knowing your purpose beforehand allows you to direct your conversation on track and never get lost out of the way.
Starting the conversation with the right topic sets the tone that brings both parties at ease. In some occasions, you will find yourself speaking to a person who keeps bringing the conversation to a dead-end.  You ask the question, he gives you the answer and period. A constant change of topic just because the previous one died immediately, makes both parties start to feel uncomfortable. However, it is fine to move on to a different topic or jump into several if the discussion flow continues and does not leave a dead air at some point. Put yourself in the shoes of the other person.  It further elevates the conversation to a deeper rapport and better understanding of each other.

There are particular topics or statements that will be hard to understand due to the complexity of the story or simply because the environment is distracting.
Asking for clarification or further explanation is a way to show your interest in the topic being discussed.  It also shows that you are paying attention. All good points and I think there is merit in having the conversational skills to flow without intent as well.
I suppose learning to feign interest could be a useful conversation skill, but I just have no stomach to fake things. All are good point , but I think Humor the single word that makes  conversations meaningful , interesting and effortless.
Deep and thoughtful communication cannot be taught by simply reading an article, but these tips provide a good framework for your discussion. True confessions of deeply-held feelings can be painful, but no matter how staggering, keep your cool. It could be very tempting to take the statement for granted and go on with the conversation. You can make a difference in making meaningful conversations- to help another person change or simply improve your connection with a person. If you are not genuinely interested in the subject (or the person) it becomes very difficult to force a smooth conversation.

It is very difficult to carry a long, insightful conversation without the small talk first though! I can see people attracts towards a humorous personality and a humorous personality having a good social value and respect.
Put away your cell phone, and for goodness sakes, do not wear earphones of any kind while the other person is talking. A conversation like this one is a great opportunity to confess anything wrong that you have done or any secrets that you hold. That will make the conversation a "conversation" and prevent you from interrupting too much and boring the other person.
If they interrupt a lot, just interrupt back and treat that as the type of conversation it is.

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