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Ok so you FIRST have to sleep with Jak, and when you do make sure you go the tent/campfire route.

Then you sleep with Jade.

Then you talk to Florence, interview Magnolia, and make sure you TAKE the gun. (If it's not the weekend, sleep in until it is.)

Then next weekend you talk to Florence again, ask for shooting lessons and sleep with him.

Then talk to Jed, but DO NOT sleep with him. Idk if the other options work, but I flirted with him.

Then talk to Magnolia, and make sure you play her favorite song, Annie Lislie, THEN ask her to stay the night after you sleep together.

Then the next morning go to the sheriff's office. Jak should be in the cell.

Ask why Jak is in the cell, and Jed explains he was caught murdering Magnolia, then the achievement should be unlocked! I hope this works!