Halp.

An old boss of mine has a fairly high-level position at a prominent media company and I really want to contact him about helping me get a job there. Problem is, when he was my boss, I was just his secretary, so he doesn't really know anything about my capabilities in this field...I almost feel like I'd be asking him to give a dishonest recommendation because he never worked with me at that level. Also, the last time I saw him was something like seven years ago. We have mutual friends so we sometimes turn up as cc's on the same emails, and we're connected on LinkedIn, but that's about it.

I suck at networking. Any tips on how to contact this guy without making a complete ass out of myself?

While we're on the subject, there's a small publishing company based in Portland, Maine and I'd love to send them a cold cover letter and resume. It's highly doubtful they'll ever have any positions to fill -- they only publish a couple of magazines and their entire staff is about a dozen people at most. Would it be ridiculous to write to the publisher and just introduce myself and say something along the lines of "if you ever have any openings" etc? Or would I be...making a complete ass out of myself?