I haven’t really roleplayed much in the past and was considering finally giving it a try. Would it be best to search for a guild to get started, or just city / walkup type stuff? Also do I need to be super familiar with the lore / story as a beginner? I’ve played this game forever, and played WarCraft III, but that’s about it.
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Honestly it can be either or. If you want more structured RP with stories I would suggest finding a guild or at least a consistent RP partner. If you are just looking for general roleplay, city RP works fine!
As per lore, a basic knowledge is a good start for beginners and you will definitely learn as you go!
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Hey there Kylanie!
Let me answer some of your questions for you real quick lol.
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Don’t have to search for a guild to get started if you don’t want to. City/Walkup RP is always a good way to get started and get into the hang of stuff. Just seeing and observing how others do it, trying it out for yourself, fleshing your character out and getting more confident in yourself is always helpful when starting out. A guild can also give you a good foundation to work off of as well, especially if they’re beginner friendly.
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You dont need to be super familiar with the lore/story as well. A lot of times just a casual understanding is all you really need. It entirely depends on the people you’re RPing with and what you’re interested in as well! Some people like to go super deep into the lore and understand every minutia of it, some people only follow what they’ve seen in the quests while leveling and the dungeons they’ve ran at end game, and some people are a mixture in between. And they’re all valid as long as they dont ruin your fun.
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Not an answer to a question, but a few Addons that can really help you are TRP3, and Emote-Splitter. TRP3 is a RP profile addon that allows you to fill out a character sheet with information about your character from height, weight, eye color, background and other information, and Emote-Splitter allows you to write as much as you want in the chat box.
Hope all that helps and hope to see you around!
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In addition to the addons that Rease suggested, I would recommend Listener as well. It really helps when you are in large groups of RPers.
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You can also go to the RP (World’s Emd Tavern) forum and ask lore questions there 
Personally as a relatively new roleplayer in videogames I’ve always found walk-up RP to be frightening. Mainly because it’s random so it always feels incredibly awkward to me (I mean in real life you usually don’t just randomly approach someone on the street and start talking like that). But then again I get anxiety when I think of randomly interacting with someone so I’m always reluctant to do it.
They are at first. I’ve been on this realm for years and now I make it my personal responsibility to find shy people like yerself and approach them even if it just for a very simple.
“Hey! Yer armor looks spiffy ta’day. Sir!”
“Okay, take care! Compliments aren’ gonna hand themselves out unless ah’ do it~.”
In time it will slowly become second nature. I have PTRD and Bipolar One… Along with degenerative discs and a really messed up stomach. Sometimes my mind fragments and I actually forget who I’ve approached. This is why I use the relationship tab when you click on a person. It is to the right of the parchment on the small trp3 mini-bar where you can read first glances.
It is interesting and something that you gotta understand and tolerate when walking up to someone. We all have our own characters and their own backstories and history. Sometimes people don’t like my character and that is perfectly fine. As long as IC is kept IC and OOC is kept OOC.
I wish you luck Nobleshield on yer persuit for RP 
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Thank you all for all the replies and advice. I’ll look into these and hopefully see you in the world.