Quote Originally Posted by GrottoSteelKlaw View Post
This may seem very silly of me to ask, but as someone who has had 4,5 or 6 years of D&D experience under there belt and still know nothing, how have I not learned? (and possibly a continuation of another post I made, I think it was my first one on how to speak up.)

How do I roleplay and how do I have fun with it?
Based on what you've said (and much of this has already been discussed by others), I see at least two and possibly three problems here.

1. You are not very familiar with the rules, and because of that unfamiliarity, you feel overwhelmed by anything that requires decision-making. This is a significant issue, as roleplaying is a constant rolling process of decision-making; it is an ongoing impromptu (or extemporaneous) improvisational acting exercise, where you "make it up as you go," within established limits.

2. You are generally a quieter, more listening-focused kind of person. This helps you in combat, where you have a solid grasp of what is going on and can identify strategic decisions quickly. However, out of combat, it sounds like you are somewhat overwhelmed by the speed and amount of information you have to process. Combat gets divided up into discrete rounds and turns, but roleplay is done "live," which sounds like it daunts you.

3. Possible extra problem: Your preferred kind of roleplay may not be in the same style or at the same pace as your fellow players. If this is the case, it'll be tricky to solve, but not necessarily impossible.

Obviously, for point 1, the best thing you can do is really try to familiarize yourself with the rules, and develop tricks and techniques to make it easier to play. Three things that help a lot of people, regardless of edition, are (1) carefully reading all of the official material about your class; (2) getting very, very familiar with your character sheet, so you know exactly where all the relevant numbers and information can be found, and can even use it from memory; (3) reading as many online/player-written guide info as you can stomach, so you can develop initial intuitions about what is and isn't valuable for that class to do. These three elements, plus some other tricks (like preparing commonly-used actions or spells on flashcards), can significantly reduce any overhead you may experience due to unfamiliarity, allowing you to play more "naturally," without apprehension or self-doubt that could interfere with roleplay.

For point 2, all I can say is that practice and comfort are the two most important things. You need to be comfortable with the character you're playing, and the people you're playing with. The former I usually dealt with early on by (for lack of a better term) "playing myself." That is, playing a character who was an intentionally idealized version of my own beliefs and personality. They aren't me--remembering the separation between self and character is extremely important for roleplaying, to avoid feeling insulted or personally attacked--but they're enough lke me that I can reliably just...react as I personally would react to a situation. This makes the acting natural, unforced; I need very little pretending to play this kind of Let's Pretend (or, rather, my pretending can be focused on the scene imagined in my head, rather than simulating an artificial person). Once you have that place of comfort you can start from, it's all about practicing. Keep at it. Throw yourself into situations you aren't comfortable with to see what happens. Be willing to risk looking like a fool; if you always play it safe, you'll almost always be stuck playing it silent too. That doesn't mean you have to be constantly speaking though! Interjecting only when needed with clever ploys, requesting more information as your character observes their surroundings, and absorbing and processing what's going on are perfectly valid ways to roleplay.

If the third point applies, you'll want to get some time away from the formal game table to just...talk things out with your DM and fellow players. Be open and forthright, while emphasizing the positive--not always easy, but always worth pursuing. Tell them you're feeling sad and frustrated and worried, and that you want to work with them to address this so everyone can have a ton of fun. I guarantee you that, if they're even slightly friendly, they'll respond positively--and if they don't, you NEED to get out of that group anyway. It sounds very much like your DM can pick up on your particular cues, even if they don't know precisely what those cues mean, so you're already in somewhat good shape there.

The keystone for all relationships of any sort (from gaming to love) is C4: clear, constant, candid communication. Speak up when you have a concern. Talk about how you feel, and if you have any guesses as to why, share them. Don't conceal the truth in general, and certainly do not do so solely to avoid hurting feelings or to avoid "rocking the boat." The boat is already rocking, speaking up is an attempt to stabilize it. But while dodging painful truth solely because it may be painful is not helpful, wielding the truth unwisely is almost as bad, as it creates problems in the attempt to solve them. Don't let your C4 turn into an actual explosion: focus on (a) the positive, and (b) places where you can see potential for improvement. The truth is not an excuse, nor a shield, nor a crutch; recognizing it and sharing it wisely are distinct but related skills.