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I messaged a guy who works in a city department awhile back on Facebook who's an alum of my school, asking him what he thought of the current employment landscape and what he thinks of people going to law school. He gave a lengthy, thoughtful response, and that was that. Over a year later, he's the OCI interviewer for this agency, and I would desperately love to work for them. I have two options (or a combination of both):

1. Reach out to him on Facebook after being incommunicado for over a year, telling him that I did indeed end up going to law school, I'm doing work in tandem with his agency in another part of the government (legitimately--I don't want to divulge too much for fear of losing anonymity), and basically express interest outside of the formal application process.

2. Have someone else in the city ask them to pull my resume. I think if they did that, it would be more than enough to get an interview, since I'm basically working with them already.

Is it inappropriate for me to get back in touch with him on Facebook? Too desperate/pathetic?

Definitely reach out.

My story: Met a lawyer at an amazing firm right before law school when trying to decide what school to go to. He went to X school. I was deciding between X, Y, and Z. X school connected me and him and we had dinner. Didn't get in touch at all after, except I sent a nice email saying I didn't choose X school, thanks for taking time out, etc. Flash forward, a year later, I finish 1L. I find out I have a CB interview with his firm, link up with him, and he was nice enough to put himself on my CB schedule.

It is a very good signal to the agency/firm that you have enough social skills to simply reach out to someone in a polite and succinct manner. It definitely gives a bump over your peers.

Only the squeaky wheel gets the oil, and if you don't "reach out" somebody else will. Use whatever connections you can muster. Headhunters and recruiters respect people who know how to hustle and aren't afraid to get in their faces.

I would reach out. I don't know what the process in the city is, but usually governments have some process in place where you have to disclose connections anyways.