If you've already applied for this year, and are trying to talk to the dean to sway his decision, it'll probably look like kissing up. Just sit back and try to relax, but consider the possibility that this isn't your year. Devise a Plan B.
I wouldn't go out of my way to specifically talk to the dean, (there are plenty of other "important" people without a big title) but if applying next year, you should definitely make your interest known.
1. Email specific faculty with specific questions about programs you like.
2. Request brochures, etc.
3. Don't hesitate to ask a few important questions about applying (I had to email the adcom of a school for a Q on LOR's)
4. Take extra time on your secondary for that school
5. Visit the school if you can, meet people there, be friendly but not overbearing.
I wrote a letter of interest for my top school, and mailed it a few days after my secondary. I very sincerely stated that their school was my first choice, elaborated briefly on why, and indicated a specific program that I liked at their school.
I interview at my top school in a few weeks.
Just remember the KISS principle (keep it simple, stupid)
-NS