Order Up

Order Up is a side quest in Fallout 4 that takes place at Drumlin Diner. Trudy, the owner of the diner, can be heard arguing with Wolfgang over Trudy's son Patrick's debt. For all available options, talk to Wolfgang to begin the quest.

Detailed walkthrough
When the Sole Survivor discovers Drumlin Diner, they will hear an argument between Trudy and Wolfgang. The player can:


 * 1) Enter the diner and talk to Trudy. All conversation options result in her offering money for the player to kill Wolfgang.  The player can ask for extra, accept, or refuse.
 * 2) Talk to Wolfgang. He and Simone will initially draw their weapons, but it is possible to ask what's going on.
 * It is possible to threaten him to lower his gun, then subsequently extort him for money, with a third check to get him to run off entirely. If the intimidation fails at any point, he and Simone will turn hostile.  If they are killed, Trudy will reward the player.  Until the third Charisma check, it is possible to ask what's going on, offer help, or make a sarcastic remark.

If Wolfgang isn't hostile or hasn't been driven off, he will ask for help, with either talking some sense into Trudy or taking her down.
 * The player can ask about Trudy. Wolfgang explains how he got her son Patrick hooked on Jet.  The player can agree that they should pay what he owes, that Wolfgang's a scumbag for making him an addict, or that they're both in the wrong.  The conversation returns to his offer.

The default payout is 100 caps, but the player can haggle for 125, 150, or as high as 200 (unless they hustled him earlier), to agree to talk to Trudy or join them in the attack, the latter of which turns Trudy and Patrick hostile.

Talking to Trudy after Wolfgang results in her refusing to pay up. The conversation can take one of a few turns:


 * 1) The player can offer to help her instead, in which case she'll offer 100 caps to kill Wolfgang. This can be haggled up to 125, 150, or as high as 200.  Refusal to help turns her hostile.
 * 2) She can also be convinced or threatened to pay up. If the "end peacefully" option fails, the quest defaults to her offer to kill Wolfgang.  If the "Threaten" option fails, she will turn hostile.  If either option succeeds, the standoff comes to an end.

By this point, talk to whoever is still alive to complete the quest:
 * If Trudy is killed, Wolfgang takes over behind the counter and becomes available as a chems merchant.
 * If Wolfgang is killed or driven off, Trudy remains and becomes available as a general goods merchant.
 * If Trudy is convinced to pay up, she remains behind the counter while Wolfgang leans up against the wall outside. Both become available as merchants.