It's actually not a bad idea, man. Going sly with your friend...you may not fully understand what he's going through, but it shows empathy and a lot of brotherly love. For me PERSONALLY, if a close friend of mine was talking about it with me and I was on the fence, just the thought of him being willing to do it too would spur me on. I wouldn't accept him doing it on my behalf...but once your friend goes bald, don't be surprised if he starts talking to you about how cool it is.
My friends joke constantly about my head...how I am always talking about the freedom I feel...I share comments from ladies...the wicked glare I get on my head! I just can't shut up about my head or stop showing it off. lol
One friend of mine has been bald since around '99. He was confused about my excitement...he seemed to think I had been shaving for a long time. I told him I had just passed my first month, and it all made sense. He remembered his excitement and joy over going bald, too. And we shared some stories and bonded closer over BEING BALD of all things.
So yeah, JUST about everyone here is a success story in one way or another. But I think you should go bald yourself...show your friend that it's not something to dread.