(First off, let me give a special thanks to Jhared/Eyildr and whatever other characters he might be playing, simply for writing a guide on forum etiquette long ago which initially inspired me to write this guide. Also, let me just say that this is by no means a "You should do this and nothing else"-guide. It's meant to give beginners some basic insight, not lecture people who have already roleplayed for years.)

How to hold a conversation in roleplay!

Foreword

During my relatively short period of roleplaying in the glorious World of Warcraft (1-2 years), one issue that has been almost overwhelming time and time again is that of continuously seeing people with a complete lack of social ability and charisma - that's not to say that everyone's meant to be a people magnet, but there are so many people who just don't talk. The kind that you eventually grow frustrated with. However, this guide is not intended to thrash these players, but to aid them in improving their social roleplay. While I might not always be much of a talker in the offline world, I consider myself at least averagely socially trained - that is, trained in the knowledge of etiquette, consideration of other people and the importance of interest.

Conversation is the bread and butter of character progression. Pre-scripted events don't bring life to your character nearly as much as normal talking does. Sometimes you will meet people who are all action and no talk, of course. They might seem awesome with their cold, dark gaze and clean, flawless skill in battle, but ask yourself this:
"Will they ever become someone of significance? Will they ever have anyone to rely on?"

You'll find that the answer is usually, "No, these are characters that fit well as support characters in single-player games, movies and books; not in roleplay environments."

I wrote this guide in an attempt to potentially teach the less talkative people of our local roleplaying servers how to hold a rich, light conversation without the stern tension of awkward silence and superiority. That's just no fun, is it?

Introductions - "First impressions are everything."

When you meet someone new, never expect them to know who you are - no matter if you are the infamous beggar of the Old Town or the Grand Marshal of Stromgarde. Sometimes, you'll encounter someone who knows very little of everything; their character might be an illiterate, uneducated son of a retired traveler who lived in the jungle for most of his life, or the player might simply be new to the server. Introduce yourself or ask them to introduce themselves; just do it naturally as you would during any day in the real world.

There is one golden rule that is important to follow here: Always try to be polite, to a moderate extent (as much as your character lets you, that is; everyone's different). If you boast about your merits or act all superior on them, they will be largely discouraged to talk. And that's no way to make conversation at all!

There are specific things that are often good to avoid when introducing oneself or talking to someone for the first time, of course. Examples:

When you spot a damsel, it's generally inadvisable to approach them with a pick-up line. It often backfires entirely and makes you look bad. Even the most charming of gentlemen know not to make a lady blush at once!
If you approach someone with a direct, admirable compliment, the effect is often that of making your character look like an inexperienced child. It's understandable that characters are different from character to character, but there are certain limits to politeness.
Rude language. When you walk up to someone, you'd never say "What the **** are you wearing?", would you? No. I'm pretty sure that not one single person on these servers would ever do that with serious intent in real life; it's just one of those logical things born from common sense that many characters seem to lack.

Don't just sit there like some sort of Ranger of the North with romance issues - go out there, take initiative and have fun! Just don't be a creep. Personal questions are not to recommend for starters. Social discretion and integrity are the safety nets of a conversation.