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In a perfect world, an employee’s relationship with his or her supervisor would be an affable yet respectful one based on trust, communication and a sense of working toward a common goal. But don’t get too comfortable. Friendly workplace repartee is fine and all, but as a rule of thumb you should always think before you speak in the presence of an authority figure.

Below we’ve rounded up eight cringe-inducing things that you should never say to your boss unless you’re itching for an awkward censure session, a good, old-fashioned chiding or even a pink slip. And these count for telecommuters, too; just because you don’t see your supervisor on a regular basis doesn’t mean you can set them up on hot dates, discuss your wicked hangover or complain about how horribly bored and unmotivated you are.
1. Did you hear that hot gossip about Andy in IT? Scandalous, am I right?
2. Can we talk about that gift subscription to the Jelly of the Month Club?