On the 14th of Fall, Duke will come by your house and ask if you could help them harvest the winery's grapes. If you agree he'll ask you to come by at 10:00 am the next day, and suggests that you find a partner to help you harvest. The only person who doesn't really have a job is Cliff, so meet him at the Church or in the Inn and ask if he would like to help.
At 10:00 am on the 15th go to the winery. Manna will ask if you can help them for a few hours. If you agree then you and Cliff will talk with Duke and harvest the grapes. You don't get to pick the grapes but it's done automatically for you. At the end of the day Duke will thank you and Manna will feed you some wine and cheese. Yummy! Duke is so impressed with your partner's work that he offers Cliff a permanent job! Cliff thanks you for inviting him to the winery.
Now instead of hanging out alone in the Church, you'll find Cliff downstairs in the wine cellar. You have to invite Cliff to work with you if you want him to stay in town. If you don't ask for his help Cliff will leave town at the end of your first year and he'll never return.
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