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 is also possible to start the quest by simply entering the inn for the first time, and after entering you will overhear Vadim telling a story to a man named Hawthorne. After this conversation, leaving and re-entering the bar, you will pick up the quest by talking to Vadim.

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 player's assistance in it. The fight takes place at 6:00 PM that evening, or the next one if it's already past this time when starting the quest. Return to the inn then, or find a seat to wait out the time.

Once at the bar, Travis will be seen making his way inside towards the bar counter and is confronted by Gouger and Bull, two raiders 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 that 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 Sole Survivor 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.
 * This bug can also be resolved on the console version of the game or without using console commands by loading a save file that is from a point before the player speaks to Travis to initiate the bar fight. The player must then go to Beantown Brewery (without talking to Travis) and kill Gouger and Bull who will now be killable. The player can then 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 Gouger and Bull start to leave, enter the following console commands which allows them to be killed: ,
 * This bug has been reported as fixed in patch 1.2. 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 Gouger and Bull should be non-essential again.
 * The player can also reload a save prior to entering Bean Town Brewery when prompted to meet Travis before entering. If the player bypasses interacting with travis, engages no enemies, and rushes to engage Gougar and Bull, they are not represented as essential, and the quest can be completed regularly.

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