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I heard about the Thieve's Guild, and I want to know how to join it. I really need some extra cash since I'm always raiding places and bribing guards. I can't really fight them and get money from their corpses, since I suck at combat.

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To join the Thieves Guild, travel to Riften and come into contact with Brynjolf, who can be found at the market stalls or the Bee and Barb tavern during the day. Brynjolf will approach you and question your wealth, before inviting you to help him with a little plot. This begins the first quest, A Chance Arrangement, in which you must steal a ring and plant it on another person. If the quest is failed, Brynjolf will still give you the next quest. Travel down to the canals and enter The Ratway. Defeat the bandits and follow the tunnels to The Ragged Flagon, headquarters of the Thieves Guild. Here, Brynjolf will give you the next quest, Taking Care of Business, tasking you with roughing up three business owners for debts he needs collected.

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Someone will approach you in the bee and barb in Riften, he will then ask for your wealth before you can start the quest.

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    This is a repost of the accepted answer at best and misleading at worst.
    – Comic Sans Seraphim
    Jun 22, 2015 at 20:09

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