This achievement occurs during Episode 3 - Citizen Brown
After returning back from dropping things off at your home you'll be back in the town, do the following:
• Walk over to the statue in the center of town square.
• Interact with Lorraine.
• Dialog (Lorraine): "Ask about flask."
• Interact with Statue.
• Interact with Statue (Again).
• Walk around the statue.
• Interact with Lorraine.
• Walk around the statue.
• Interact with Flask.
• Walk over to the courthouse.
•
Use Item "Lorraine's Flask" to equip.
• Interact with Officer Parker (With Lorraine's Flask equipped.)