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Red Dead Redemption Who Are You to Judge - Getting Started
In order to begin the Red Dead Redemption "Who Are You to Judge?" side-quest, you're going to need to Rathskeller Fork in New Austin and seek out a man named Jeb Blankenship. There should be a "?" mark on both your Main Menu map and mini-map --though if you're not close to Jeb the symbol won't appear on the mini-map until you are.
Once you're close enough to Jeb, a cut-scene will begin where he asks Marston for help. At first, Marston is annoyed at the plea saying "You and every fool around here," but he then decides to help anyway. Jeb's request is that Marston tracks down his "lost love", who has apparently been kidnapped by gangsters over at Tumbleweed.
So, of course, that's where you'll want to go next.
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Finding Jeb's Lost Love
Once you arrive at Tumbleweed there is a high chance that enemies will appear from the hideout. If this happens you will need to take them all out first before you can continue on with "Who Are You to Judge?". Once the gang hideout has been taken care -- if you were forced into it, that is -- search around for a woman standing next to a horse. Approach her and a cut-scene will begin.
In the cut-scene Marston will assume that the woman standing next to the horse is Jeb's "lost love" and tells her why he's here. The woman will then begin to laugh and, simply put, will call Marston an idiot. Later on in the cut-scene, Marston finds out that it's not the woman that Jeb wants back, but rather the horse. That's right, Jeb's supposed long lost love is the horse that the woman (who's name is never mentioned) bought off him not too long ago.
She agrees to give the horse back to Jeb, and so begins a horse ride back to Rathskeller Fork. The unnamed woman will be the one riding Jeb's horse, and you're given the option to either ride close to her -- which will start a conversation between the two -- or to simply gallop to Rathskeller Fork and have her meet you there. In order to not ride along-side her, you'll need to be at a certain distance away from her. This can be easily achieved by rushing ahead of her.
Once you've reached Jeb in Rathskeller Fork, it's time to tell him the good news.
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You and the woman will approach Jeb with the horse, and Jeb, of course, is overwhelmed with joy at the sight of his long lost love in a cut-scene that follows. Marston will make a remark that Jeb is messed up; the woman tells him that the heat does that to people.
The cut-scene then ends with Jeb thanking Marston greatly for re-uniting him with his long lost love. The Stranger quest then ends with Jeb saying that he's got a lot of "catching up" to do with the horse -- what exactly he does is unknown. The quest ends there.
If you pick up a newspaper later on, there will be a news post informing readers that Jeb officially married the horse.
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All screenshots and references from Red Dead Redemption.