Girls will sometimes not show up at the location for the date causing it to automatically miss. Sometimes will receive a missed date prompt even if one hasn't been set or was previously done.
Emily after sleeping with her in her room at night. The next day I wasn't asked for a date, but was given a "you missed our date" dialogue followed by loss of affection. I haven't attempted to try it again since I declined her each time she would ask (which was often) due to try to focus on the new content added.