Dear Businesslady, My roommate is preparing for an interview for a position with a different team in the same large organization where he works. He met up with the person who referred him to the position, a former colleague, for coffee and learned for the first time that this very same person would be his supervisor if he were to get the new position. This understandably changed the tone of the conversation, and it turned…

Dear Businesslady, I am deeply, frustratingly, maddeningly in love with my female boss. I am also a woman, and I identify as "mostly straight" -- I have only dated men but have had two other deep, frustrating, maddening, ultimately unrequited crushes on women. My boss is five levels above me. She is one of the heads of our company. She knows how I feel, at least in a jokey sense, because our office is…

Dear Businesslady, I have a question about something that (I don't think) has actually affected me yet, but I fear that it could one day, and I would like some advice. I have an unusual name. As far as I know, everyone with my last name is at least distantly related to me, including another woman with my exact same name who is around my age and the daughter of my dad's third cousin or…

Email us questions at advice@the-toast.net, subject line “businesslady.” Previous installments can be found here. Dear Businesslady, How long can I wait to quit after accepting a promotion at a workplace I dislike? Despite the fact that I wanted to turn down said promotion and stay in my old position...I took it. At the time I was in the midst of trying to get the heck out of…

Email us questions at advice@the-toast.net, subject line "businesslady." Dear Businesslady, The other morning I woke up, thought about going in to work, and was just like “nope.” I called in sick, then spent the day catching up on a bunch of chores that had been stressing me out for ages (along with spending some quality time binge-watching TV). I do this periodically, and it always makes me feel much more refreshed when I go…