Lets Play Skyrim Part 11: Joining Thieves Guild Walkthrough
5To join the Thieves Guild the Dragonborn must enter Riften and speak to Brynjolf, a red-headed Nord male, who can be found during the day in the Riften Marketplace between 8:00 a.m. - 8:00 p.m or in The Bee and Barb at night. Once the Dragonborn is within proximity, Brynjolf will automatically attempt to strike up a conversation in which the Thieves Guild prerequisite quest "A Chance Arrangement" can be started. Alternatively, in the evenings past 8:00 p.m., the Dragonborn can encounter Brynjolf at The Bee and Barb inn, at which time he will tell the Dragonborn to speak with him during the day at his stall in the Riften Marketplace.
Brynjolf, when encountered during the daytime, will give the Dragonborn instructions to steal Madesi's Silver Ring from the strongbox located under his stall and then plant it inside of the pocket of Brand-Shei, the local general stall owner. He is identified as the only male Dunmer in the crowd. Brynjolf will start a distraction by calling everybody within the area to listen to the story of his latest product that he is selling, which is obviously a ruse. During this time, carry out the plan as discussed with Brynjolf. Planting the ring will instantly end Brynjolf's tale he is telling to the crowd thus dispersing it. He will now tell the Dragonborn to meet him in the Ragged Flagon down in the Ratway to discuss membership.
Even if the Dragonborn fails to acquire the ring, joining the Guild is still possible because Brynjolf says he still believes the Dragonborn has what it takes despite failure of the quest. It will however make a few members of the guild treat the Dragonborn with more disdain, initially.
http://elderscrolls.wikia.com/wiki/Thieves_Guild_(Skyrim)
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