Moonlight Peaks incorporates dating mechanics that exceed the complexity typical of farm simulation games, enabling players to pursue relationships with multiple townspeople through activity-based outings. To initiate dating, players must first achieve a four-heart friendship level with a chosen character and then select the appropriate dialogue options to request an outing, which will commence during the following in-game night.

The system permits simultaneous relationships with multiple characters, though the game includes a technical quirk where requesting dates from several people in a single night may cause them to queue unpredictably. When this occurs, the most recently invited character will be the one to collect the player, creating an order that cannot be tracked within the game, prompting players to space out multiple date requests to avoid complications.