My Sharp-Tongued Boss

Dear Meg,
My 83-year-old boss says things to me that are pretty offensive. Yesterday, she told me if I dressed better I would be married by now. I’m 32 years old, and if I wanted to be married, I’d be married. All I do for her is run errands and keep her house in order. How can I kindly suggest that she keep these opinions to herself?
— Charlie

My Dear Charlie,
I’m guessing the two of you never agreed on a dress code? I know it’s hard to tolerate the values, social norms, and expectations of people who grew up in a diiferent time and culture. The comments of your employer are probably only meant to be helpful, but she is delivering these zingers with no prompting from you, and this is outside the parameters of your relationship.

You need to ask to meet with her at a specific time to discuss this problem. I suspect she values your work highly or she would not be concerned with your personal life in the least. Tell her how it makes you feel when she says these things and ask her if she might consider a little restraint of tongue in the future. Ask if your wardrobe has become a concern to her as it pertains to your work only.
You already know how to do this, Charlie. You employed the patience necessary by writing to me before flying off the handle. I think you and your boss are learning quite a bit from one another, and it’s going to turn out fine.
Love, Meg