Get your own state of mind. You are following him.
Trust what you read and keep trying to do that and not just what he is doing. Once you are behind him he is fast because you are in disturbed wind and unless you sail your own race you are doomed. He is subtly destroying your confidence and stroking his ego.
Here are two things that will make you much faster. Stay very quiet on your boat, move the rudders less and most importantly when you are behind him move off his rear end.
Also. Think a long way ahead. Do not react on the boat. Predict and make quiet moves to create what you see in your mind to be fast.
When that turns out to be slow think through why and make notes not to repeat slow behaviour.
Also, he knows you so do not do what you always do. When you might usually tack to floow do not. Stay on course for even only ten seconds more first.
Start to play on his mind.
It won't happen overnight but it will happen.
Thanks for the advice. If we race (as opposed to just tool around) I will take you up on your suggestions.
For now, we are just playing. It isn't about head games or my confidence, in fact I am often in front when he just moves beside me and goes ahead. Next time we sail (hopefully in the next couple days) I am going to trade boats and see what happens.
-Tom