Last pregnancy I told my boss pretty early on because she had noticed I was looking awful and asked if everything was okay. I announced to my coworkers a few weeks later. This time I was planning to tell my boss and coworkers at the same time at our holiday dinner (since it will be obvious when I don't order a drink). There's only 5 of us at dinner. But now I'm thinking, wait, should I tell my boss privately first before dinner? Does it matter? What would you do?