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 a little argument between Trudy and Wolfgang. Approach Wolfgang to begin the side quest.

When one approaches Wolfgang, he and Simone will draw their weapons and tell them to leave. They can either talk normally, or threaten him. If one fails to intimidate him, he and Simone will attack them. When the Sole Survivor kills him, Trudy can be talked to to complete the quest. If one threatens him successfully, one can either continue the conversation or demand money from him. If successful he will give the Sole Survivor a varied amount of caps, or else he will attack them.
 * If one was successful once again, they can demand they leave, they will attack if unsuccessful and will leave if successful. Talking to Trudy will complete the quest.

If one threatens him successfully before they can ask him for more money, he'll tell them he would but they took it all, they will get 100 caps after completing the quest if this is the case.

If one didn't threaten him, they can ask for more money 3 times. The first gives them an extra 25 caps, 125 overall. The second gives them another 25 caps, 150 overall and the final give them another 50, overall 200.

After this little money debate, one can either choose to kill Trudy and her son, or talk to her. If you choose to 'Join the Attack', they will kill her and her son then receive the agreed amount of caps, Wolfgang will then take over the diner and become a chem merchant.

If you choose to 'Talk to Trudy', one will have to go into the diner and convince Trudy to pay. Once one talks to her, they have 2 options:
 * The first is to threaten her. If successful she will pay and one will be rewarded by Wolfgang. Wolfgang will hang around just outside and both will become merchants. Trudy is a general merchant. If unsuccessful, she will attack
 * The second option is to 'End Peacefully', if successful, one gets the same result as above. If unsuccessful, one will be asked to kill Wolfgang. They have 3 options: Yes, No, and Ask for Money.

Yes results in one killing Wolfgang and getting paid 100 caps, Trudy then becomes a merchant. No results in her attacking the Sole Survivor and Wolfgang becoming a merchant.

One can also offer her help. They'll get the same result as above.

If one passes all the speech checks with Wolfgang, they only need to talk to Trudy to complete the quest.