Dear Prudence,
A former co-worker, “Charlotte,” and I had a great working relationship. She left for a new position elsewhere because she began dating the company’s president, my direct supervisor. Our company is very small and she’s been giving the president feedback on different projects. Her help makes me uncomfortable. She isn’t an employee anymore, but the president and vice president take her advice, even if she’s unqualified to give it. She now wants to take me out on “girl dates,” has offered unprompted to teach me to wear makeup, and invited me to go shopping with her. At a group dinner, she told me my boyfriend would do better if he acted “more normal.” I think we are incompatible for friendship. I don’t want to snub her and potentially ruffle the relationship I have with my boss, but I also don’t want to keep dealing with veiled insults. I feel trapped and obligated to spend time with her to keep a job I otherwise love. To make matters worse, she’s started emailing me with assignments to complete! Help!