Cliff is a wandering traveler who has found himself in Mineral Town. He is shy and distant from everybody, and can be found at the Church. He is especially shy around Ann, who will be your rival for marriage in the girl version. When he isn't at the church, he stays on the second floor of the Inn.
In Fall of the first year, he's thinking about leaving permanently. You can get him to stay by asking him to help out at the Winery during the Fall. If you've done this, Cliff will stay as he finds permanent work at the Winery. If you do not, Cliff will leave Mineral Town permanently. If Cliff does leave town, you will still receive a New Years card from him every year.