Yes. He's a complex guy in some ways. He read my e-card this a.m. (got the notification, not a response from H). It was a cute card with drinking cows and I put just "Have a Guinness for me." This is personal in that we like Guinness and often went out for the holiday with friends and have traveled to Ireland together. But not pushy or M focused. (at least was my take-- if anyone thinks this was too much, let me know).
I did mention to H a while ago that I was having difficulty making a web site... but did not specifically ask advice. He volunteered the info about the template site.
Interesting thought about the approach... yes, my monitor had died and H answered Qs on places to look for a new one, but had no interest in helping out. Yet also seemed annoyed when one of our mutual friends offered the next day to come pick one out with me (and carry it--boy, they are heavy!) saying it was a not a good choice of model I ended up with.
Both times I asked for his advice noting this is his expertise and that I trust his judgment more than other people I know who also could give advice on hardware. I do.
When the computer died, I was a little more distressed (obviously--thought I'd lost all my files), and I'd waited a few days before coming to him, hoping I could fix it myself. Told him that too.
He said-- "in this situation, the best thing you can do is to call me."
I think my overall approach was pretty similar in both cases-- I think it was more a matter of timing. I know what you mean about the approach making a difference though. I can see many places where my approach elicited a certain kind of reaction from H in other areas!