Confidence Man

Confidence Man is a side quest in Fallout 4, where you help the Diamond City Radio host Travis Miles gain confidence.

Detailed walkthrough
To start this quest, speak with Travis Miles at the Diamond City Radio station in Diamond City. After this, you will have to wait until an NPC, such as a guard, tells you in passing that Vadim Bobrov is looking for someone to help him regarding Travis at the Dugout Inn before you can start the quest, or speak with Hawthorne at the inn and go to the locations he provides and then return to speak with Vadim. It can also be started by speaking with Vadim if he calls you over, in his bar, and asks you questions about of Diamond City Radio.

Vadim will ask you what you think of Diamond City Radio's host, Travis. Whatever you answer with, the conversation ends with him saying that Travis could use some confidence to better his radio show, asking the Sole Survivor if he wants to help. When agreeing, Vadim can be pushed to offer caps through three speech checks of increasing difficulty and amount. Whether successfully pushed or not, he says he's going to stage a bar fight that night and requests the players assistance in it. The fight takes place at 6:00 PM that night, or the next one if it's already passed this time when starting the quest. Return to the Inn then.

When arriving, Travis will be walking from the door of the bar inwards and is confronted by Gouger and Bull, two others Vadim hired for his staged fight. They begin to verbally harass Travis, who meekly replies, initiating the plan. At this point, the player needs to speak to Travis and convince him to stand up for himself. However this is done, a fistfight starts after the dialogue ends between the three and the Sole Survivor. Help Travis fend off the two using melee attacks to beat them into submission. Speak with Travis after the fight, who expresses thrill at what took place. Once he begins leaving, speak with Vadim.

If speech checks were passed, Vadim will give the promised amount of caps as he thanks the Sole Survivor. His next plan is to hook Travis up with his bar waitress Scarlett, further wanting to ensure he successfully becomes confident. Find and speak with Scarlett in Diamond City, convincing her to meet and talk with Travis. Once she agrees, head back to the Dugout Inn.

When arriving back, Yefim Bobrov will inform the player Vadim has been kidnapped by Gouger and Bull for him not giving in to their demands of owed caps for the services provided. He pleads for help, but doesn't know where they took him, saying he needs to stay and that Travis should be spoken to. Go to Travis' radio headquarters to talk with him, telling him what happened to Vadim. In the conversation, he'll say Vadim is probably at Beantown Brewery and requests to go along and help, which he does.

Meet Travis outside of Beantown Brewery and talk with him before heading inside. The building is held down by a raider gang and is full of its members. They'll need to be fought through in order to get to the room Vadim is being held in, which is guarded by Tower Tom, the gang leader. Once he and all surrounding members are dead, Travis and the Lone Wanderer can enter to untie and free Vadim. Speak with him, and then Travis, who now has a new outlook on life with all that's happened to him. With this change, he thanks the Sole Survivor, returning to his radio station with newfound confidence.

Bugs

 * There is a glitch that causes both Gouger and Bull to be set to essential, making the quest impossible to complete without the use of console commands. Two possible fixes are detailed here and here also this bug can be resolved on the console version of the game or without using console commands by loading a save that is before the player speaks to Travis (the objective "speak to Travis") The player must then go to Beantown Brewery (without talking to Travis) and kill Bull and Gouger who will now be killable. Then the player can continue the quest as normal.
 * The easiest way to deal with this bug is before it becomes a problem. After the fight in the bar, as Bull]] and Gouger start to leave, enter the following console commands. This will allow them to be killed. ,
 * Note, this bug has been reported fixed in the update available on Steam. However, if this glitch is still encountered, simply load a save prior to talking to Travis and exit the Dugout Inn. Once you re-enter Bull and Gouger should be non-essential again.
 * Following the quest "Confidence Man", Travis might not go back to Diamond City. Diamond City radio will not play and may require teleporting him with console commands.

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