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In Harvest Moon: More Friends of Mineral Town...
Cliff is a traveler, whom has decided to stay in Mineral Town for a while - he is staying in the inn, and visits the church every day. Carter becomes his first friend there, and Carter is always either asking you or Ann to befriend Cliff, while trying to encourage Cliff to overcome his shyness... when Autumntime comes around, Cliff will tell you he will be leaving soon, because he is running out of money to stay at the inn... If you do not give the job offered to you by Duke to Cliff, he will leave in the Wintertime, if you do offer it to Cliff, he will stay, and could become your husband, or a husband for Ann. (same thing happens in the original version of the game, only you may not marry him, and he can still marry Ann).
That is why he is visiting Mineral Town, and why it bothers him so... And Cliff will even say that Ann's smile reminds him of his sister.