It's tough, especially when the person is a former supervisor or some kind of higher-up writer or exec. I've definitely struggled with how to do this. I think it helps to focus on successes: keep up with what the person's done, what their company has set up, scripts that have sold, movies that have come out, shows that have gotten picked up, that sort of thing. Who doesn't like to open an email of congratulations? I guess if the people don't have a lot of press about them or their companies, it's harder...but you can maybe ask what they've got going on. Also try to keep it short, maybe just a couple sentences. People in Hollywood sift through hundreds of emails a day and definitely don't want to read novelistic ones.
If they don't answer, they don't answer - not every contact you make is going to come through for you. But it's worth a shot.
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If you're in or around L.A. or wherever your contact is, asking them to grab coffee every 2-3 months isn't out of the question. That way, it makes the whole "hey, how are you!?!" e-mail a little easier and you're not checking in 10 months down the line and prodding for job opportunities IMO.
Obviously, some contacts are more willing to meet and talk occassionally than others, but the one's who don't meet probably wouldn't be available to help much anyway? The people who are responsive and proactive in keeping a relationship should be your top priority. Keep close ties with them and try to foster a mentor/mentoree relationship. That is ideal.
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