Instructions
Walk up to any citizen and press "A" to accept her friendship quest.
Complete the given quest, earning one guild seal. It is always a fetch quest, and it will always be marked on your map. Return to the quest giver to complete the friendship quest, prompting a relationship quest.
Press "A" to begin the relationship quest.
Complete the relationship quest, which is somewhat the same for each person. Each person tells you where she wants to go on her date and marks it on your map. Once there, you must perform positive actions with the "A" button to complete the date, giving you a second guild seal.