Yakuza 3

This is a piece of cake. Throughout the game, at several Smile Burgers, you'll find dates. Take these women out and choose karaoke. This is a good way to kill two birds with one stone. Though on the dates you can't choose which songs to sing, they won't always be the same ones (unless you take the same girl out twice). Once you're done dating, head over to a karaoke place alone and you can complete the others. There are only 6 or so songs and the game isn't much of a challenge. This is an easy bronze.