I go to confession pretty regularly, and I really don't do much. I seem always to confess the same sin over and over. It's not a serious sin, but if I didn't confess it, I wouldn't have anything to say. Should I keep confessing the same sin?

Confession is usually a good thing to do regularly. The confession you speak about is sometimes called a devotional confession. It is the sacrament, but it is celebrated at a time when you are not required to receive it.

The Catechism of the Catholic Church says: "Without being strictly necessary, confession of everyday faults (venial sins) is nevertheless strongly recommended by the Church. Indeed the regular confession of our venial sins helps us to form our conscience, fight against evil tendencies, let ourselves be healed by Christ and progress in the life of the Spirit".

You are obliged to receive the sacrament of reconciliation if you are in mortal sin. But you seem to be asking about devotional confession. Generally, devotional confessions should not be celebrated more than once a week. More frequently than that will wear out the priest and you. Usually they are celebrated monthly or even yearly. You should choose a schedule that works best for you.

Key to any good confession, devotional or otherwise, is the examination of conscience. This is a consideration not only of what I have done that I know offends God, but of the underlying reason I act or think the way I do. A careful examination of conscience can make the sacrament a wonderful encounter with God.