Dear June,

I recently attended an amateur theatrical production that featured a coworker. During the play, I realized that my coworker is “acting” in the office, as much as she was on the stage. Now I’m wondering whether to continue to be my authentic self or sign up for acting classes. What do you think?

— Deceived in Delaware County

Dear DDC,

By all means, take the acting lessons, real or metaphorical. Learning the craft does not mean you have to play the part.

That is the gist of my response. But I think that, despite your letter’s elegant lack of specificity, you are asking for a fuller answer: should you play the part, and how thoroughly, and what do you stand to lose? In this case my advice depends on the nature and extent of your coworker’s “acting” and, of course, your work environment.

If your coworker is just one two-faced person in a basically supportive and honest office, and if she wields little or no power over you, I would err on the side of fighting guile with unrelenting pleasantness, but I would stop short of actual dissembling.

But perhaps this woman is in a position to do you serious harm in the workplace. If so, and if there are no other ethical issues at play–she is not bullying other workers or fleecing the public, for example–you should take whatever steps necessary to protect yourself from this two-bit Machiavelli, including “acting,” at least until you can find a less stressful job. How lovely it would be if you could confront her or, better still, unmask her. The scales would fall from everybody’s eyes, she would slink off, and you would get a promotion. But alas! I suspect that, if she has come this far, she is a good enough actor that you will have to ham it up a bit yourself in order to succeed, and perhaps in order to survive, at work.

I am not talking about actual verbal lying here, mind you. But I am talking about spin, evasion, and emphasis, perhaps even some misleading nonverbal cues. You laugh at jokes that are not that funny. You keep your eyebrows in place when every fiber of your being cries out to raise them. You cultivate expressions that are blank, confident, or rapt as needed to create the most useful impression. I believe that, sad but true, there are many workplaces where none of this is wrong—or even, really, dishonest, since “acting,” as you call it, is the vernacular of that environment: saying “you’ve told us that joke ten times” or “we all know that our client is a little weasel” in such a context is not so much honesty as rudeness, and dangerous rudeness at that.

So far I have not factored in the other side of what you see as a zero-sum equation: your “authentic self.” Here, again, I think it is largely a matter of degree. If all you have to do is pretend to like one relatively innocuous coworker, your larger sense of self should remain virtually intact unless you are a delicate flower indeed. But what if your workplace feels corrupt, like Hamlet’s Denmark, making you heartsick and indecisive from having to smile, and smile, and thwart a villain? What if the stress is making you forget who you are and what you believe?

I used to think that there was such a thing as personal authenticity, that being faithful to one’s “true self” was a virtue, and that “faking it” was a personal and perhaps a moral failure. Now I am not sure this is always the case. (For a lively take on what the great Chinese philosophers had to say about the virtues of inauthenticity, check out a recent article by Michael Puett and Christine Gross-Loh in theguardian.com on April 9 of this year: “Forget mindfulness, stop trying to find yourself and start faking it.”) We are different people in different contexts, after all. There is something to be said for just getting on with life and not overthinking the issue.

On the other hand, if by “authentic self” you mean an ethical person, someone who does what he or she thinks is right, then this factor must outweigh everything–except, perhaps, basic survival. And your mental health must also carry great weight. If your coworker is part of an office environment you find toxic, feel free to chew the scenery as needed for the time being, but get out as soon as you can, and find a job where you won’t feel pressured to act a part that makes you sick.

Dear June,

I have been on four dates with a smart, attractive man. He is funny and very attentive to me. We agree on most important matters, including the need to be generous to the poor and sensitive to other cultures. But he has been rude, and quite stingy, on several occasions to restaurant staff and an Uber driver. Is this a deal breaker?

— Torn in Tulpehocken

Dear Torn,

Yes.

Cleaver’s in-house advice columnist opines on matters punctuational, interpersonal, and philosophical, spinning wit and literary wisdom in response to your ethical quandaries. Write to her at [email protected]. Find more columns by June in her attic.