Black HeartGo to the 2nd floor of the Inn on a Spring night on any day except Saturday, from 7:00 pm until 9:00 pm. Cliff will be upstairs, keeping to himself as usual, when Ann walks into his room to say hello. Cliff naturally pulls the shy-guy routine but Ann says she's just there to talk. She asks him the reason why he's moved to the village but Cliff replies that he's sorry, but he doesn't want to talk about it. Ann realizes she's walked upon a sensitive subject for him and apologizes for her question. She says she's going to go tidy up now but just before she leaves, Cliff thanks her.
If you want Ann and Cliff to marry, you must see this event before the end of Spring of your first year.
Blue HeartWalk into the Church from 11:00 am to 4:00 pm between Summer 1 and Summer 30 of your first year. Inside you'll find Carter talking with super-shy Cliff. Carter is suggesting that Cliff go out and talk to the villagers, but Cliff says it's hard to talk to new people. Ann walks in and Carter warmly welcomes her. Cliff of course can only mumble a greeting. Ann is there to deliver Carter his lunch from the Inn and she asks Cliff what he's doing at the Church. Another mumbled answer from Cliff gives Carter an idea. He asks Ann if she would be nice enough to introduce Cliff to some of the other residents of Mineral Town. Ann gladly agrees to take Cliff around town later.
You must see this event before Fall of year 1 if you want to get Ann and Cliff married. It will not occur during Fall season, and once Cliff gets the job at Duke's winery, he will no longer visit the church during the event time. If Cliff does not get the winery job, then he will move out of town permanently.
Green HeartOnce you've reached your 2nd year in the game, go to Doug's Inn on a Saturday between 11am and 1pm. Inside you'll find Doug and Ann talking to each other. Doug is wondering how long Cliff will stay in Mineral Town and he hopes that Cliff doesn't leave. Cliff then walks in and asks what the two of them are talking about. Doug tries to keep cool, but Ann blurts out and asks how long Cliff is planning on staying in town! Ann tells him that he can stay at the Inn forever if he wanted to. Cliff thanks them for their generosity and asks if they're sure about the offer. Both Ann and Doug are very sure they would like to have Cliff around forever.
Orange HeartGo to the Winery storehouse on any day except Saturday between 10:00 am and 1:00 pm once you've reached your 4th year in the game. Cliff is hard at work at the Winery so Ann has come by to deliver his lunch. Duke walks in and Ann gives him a friendly greeting. Duke asks what she's doing here and Cliff says she's come to bring him his lunch. Duke laughs and thanks Ann for bringing Cliff's lunch, then makes a small comment on how they look like newlyweds! Ann is truly embarrassed and Cliff reacts in shock! She naturally denies anything is going on and runs out of the Winery. Duke doesn't see the problem with his comment and then ask Cliff when he's going to propose marriage to Ann. Cliff is still taken back by Duke's suggestion and doesn't know what to say.
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