STORY OF SEASONS: Pioneers of Olive Town

Let me get this out of the way now: the Communication Skill will be one of your most hated to level up, simply because of the slow progress. Now, on with the guide.

The residents of Olive Town will come to be a reasonable part of your daily life as you try to make progress through the game. While I do not know if talking repeatedly to people after the initial greeting would count, you'll be needing to interact with the villagers on a daily basis as it is so there's little point to talking to them more than once. You can also talk to people during town events, prior to starting the actual event. This will come easily as you aim to romance a bachelor/ette.