Help Steve out both timesMISSABLE
After the workday on September 3rd, you'll get a call from Steve, your boss at your job back home. After a short conversation, he'll ask you to help him with some files. Agree to help him and he'll mail out the box of papers. After the workday on September 4th, your Dad will call you. After the conversation, you'll have to decide how to spend your night. The box of files will have arrived at this point so choose "Work on the Addit '87 material".
On the night of September 7th, Steve will call you again and talk to you about the monster deal he just made and ask you for another favor. Offer to help him out and after the workday on September 8th, when you have to choose how to spend your night, choose to review the contracts for Steve. When the workday on September 9th starts, the trophy will unlock.