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Scribbler sounds like he needs to remember a fundamental lesson of journalism: they are not your friends. Not PR people, not company officials, not the governor, not the child whose kitty was rescued from a tree. They are professional contacts and it is your job to get them to talk to you.
That does not have to happen on a confrontational basis. You can share coffee, drinks, lunch, tell them about your new baby or girlfriend, listen to stories about their lives.
But you must keep on your side, and think of them being on their side, no matter how cordial you are and how helpful they are to you. Once you can get this division straight in your head, then you can ask probing questions that you might otherwise find uncomfortable.
I completely sympathize with shyness. One of the things I hate most is person on the street interviews, because I hate bothering people who normally have no contact with reporters. I cringe every time I have to do one. It has not gotten easier after 25 years in this business. But I get through it because it is part of the job.
Good luck, Scribbler. At least you were concerned enough to get some advice.