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Hi. I interviewed last week with a boutique firm which I have somewhat of a prior relationship (I interviewed with them a couple of years ago, but withdrew my application after having been invited to a callback; the partner I interviewed with liked me enough that she asked me to keep her updated on my career, which I've been doing once a year as a season's greetings/hello). Now that timing seems right, I reached out and interviewed with them, but having been out of interview practice, I feel like I kind of fumbled the interview a little (it was really short, less than 30 minutes, although they told me that's because they've already know most of my past from my first interview and just wanted to see what I've been up to since then). They told me that they are looking to hire within December, but I haven't heard anything back from them since then, which I think is a little odd given timeline. Do you think it's worth-while checking in (I know that 2 weeks is pretty short, but based on the circumstances, I wonder if it would be kosher to do so)?

Bumping myself - could really use any advice on how/when to casually check-in without seeming desperate :/

Two weeks is fine. You should follow-up. Given the time of the year, it may just be taking longer to get the proper approvals for the next round.