As the Sole Survivor progresses through the Diamond City marketplace, a random NPC will mention to them that Vadim from the Dugout Inn is looking for them. Traveling to the inn, it is revealed that Vadim and his brother are looking for a way to boost the confidence of the city's radio jockey, Travis, and that they need the help of someone like the Sole Survivor in order to pull off his rather convoluted plan.
The first step of the plan, is to get Travis involved in a staged fist fight. Knowing that Travis always comes in for a drink at around 6 P.M., Travis will ask for the Sole Survivor to watch after him and help when necessary, as Vadim has hired two men to pick a fight with Travis.
The two hired goons, Bull and Gouger, will begin picking on Travis, eventually provoking him into a fist fight with the two. Knowing that Travis cannot handle the two on his own, staged fist fight or not, the Sole Survivor will need to step in and help him out.
After winning the fight, Travis will be incredulous at his newfound strength, and will thank the Sole Survivor profusely for stepping in with him.
Please note that there are two possible outcomes here. In the first one you just help Travis to defeat Bull and Gouger (they're defeated when they sit down on the floor). In the other one you actually kill them and Vadim's kidnapping (below) will never take place. The date scenario with Scarlett will still happen though.
A date for Travis
The next step in Vadim's convoluted plan, is to hook Travis up with his crush, as the bar owner has noticed the way Travis and the bar's waitress, Scarlett, have been sneaking in looks at each other. She can either be persuaded to hook up with Travis, bribed, or outright threatened. Scarlett will then travel to the radio station, and the two will have a short fling together, before breaking up.
Vadim's brother, Yefim, will then approach the Sole Survivor and ask for their help in finding his brother. It is discovered that Vadim refused to pay Bull and Gouger for their services, and in return, they kidnapped the bar owner and brought him to their hideout at the Beantown Brewery. After telling Travis of what happened and what Vadim had been doing for him, Travis will agree to come along and help free Vadim.
The party will then need to head to the power plant, which has been taken over by a raider gang under Tower Tom. In the same room as Tower Tom, Bull and Gouger will finally be encountered, and must be taken down before Vadim can be released.
Having helped the Sole Survivor take down a group of raiders, Travis will finally have found his confidence, and his radio broadcasts will become objectively better, to the relief of the Diamond City population.
Speak to Vadim
The owner of the Dugout Inn has asked me to help him improve the confidence of Diamond City Radio's DJ, Travis Miles.
Meet Travis in the Dugout Inn after 6 PM
I need to help Travis win a staged bar fight to boost his confidence.
Talk to Vadim
Convince Scarlett to meet Travis
Scarlett, the Dugout Inn's waitress, needs to be talked into spending some quality time with Travis Miles.
Talk to Yefim
Talk to Travis
Vadim has been kidnapped; Travis may know where he's been taken.
Meet Travis at Beantown Brewery
Vadim is being held in the old Beantown Brewery. I need to make sure he comes home in one piece.
Help Travis rescue Vadim
Talk to Travis
Vadim is safe. Travis has been through a lot recently, and hopefully it'll change his outlook on life.