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I Have This Boss

And he is giving me the creepiest vibes.

I recently changed jobs,. He was on the Board of Directors at my old job, and is the Vice President at my new job. He recommended me for the new job, which I thought was great. I had very little contact with him at my old job beyond board meetings and the occasional email. I got the impression that he was kind of a bro, but generally easy to work with.

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But then I started the new job, and I have to see him a lot more. In person he seems fine. But THE EMAILS. Here's the latest one today:

"We could divide the work...I was planning on sitting down at [local restaurant] one night and getting through the book.

Of course pre-ordering a cab for the end of the night first.

I really don't drink that much...just seems like I am always talking about it these days. Must be you...making me want to drink."

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He's said some other things via email that have made me uncomfortable. Nothing that is out-and-out inappropriate, but they sit right on that line. I don't know how (or if) I should deal with it right now. I have to attend a conference with him next month, but I made sure I could take my own car so I wouldn't have to drive five hours with him (which was the original plan). He's bringing his wife and I'm bringing my fiance so hopefully he won't be a creep.

I'm hoping this is just a weird sense of humor thing, or that he's trying to be friendly and coming off waaaay too friendly. Because after that last email I want to crawl out of my skin.

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