That said, the woman you describe is working in a pharmacy. That means she is coming into regular contact with sick people, and with people who have chronic conditions, like you. Your dilemma involves more than just considering your own welfare, or hers. So, unlike asking to speak to someone’s manager because he forgot to hold the pickles, there’s a moral case for speaking up. Silence means tacit approval of a situation that puts other people—especially other workers—at risk. We shouldn’t be so concerned about mishandling the situation that we choose to do nothing at all.
In the absence of legal mandates, social codes are the way we establish and maintain norms. A mask is a medical device, but also a symbol of empathy and unity. Ideally, that’s enough to reinforce the code: Everyone wears a mask so everyone else wears a mask. But the world is not ideal. When people inevitably break the code, an intervention needs to be done in a way that doesn’t further degrade the mutual respect on which this code depends. The answer definitely doesn’t involve stopping to berate every maskless person you pass on the sidewalk, no matter how therapeutic that may feel.
Whether or not maskless people “deserve” to be reprimanded, criticizing or glaring at them could very well make the problem worse. The goal is to convince people to care—to be conscious and thoughtful of others, to help keep everyone safe. It’s not a goal we’ll reach, but in a situation like yours, we can nudge ourselves in that direction in small ways.
I see three ways that you might work toward that end. Ideally, if you have a rapport with this person, there’s a way to explain your position to her. You’re a high-risk individual and you’d really appreciate it if she could pull her mask up. Statements of genuine concern followed by a request for help are generally more effective than anything that feels like scolding. Keep in mind that many people decline to wear masks because they resent being told what to do. Telling them what to do—louder or more aggressively—is unlikely to solve the problem, and likely to make it worse.
This can be difficult and awkward, especially with someone you don’t know, and especially when you don’t want to have a prolonged conversation with this maskless woman. A second option is to consider writing a note to her. This can seem passive-aggressive, so you would have to be doubly or triply sincere in showing that you’re simply concerned and that a change in behavior would mean a lot to you. Maybe include some candy.
A third option is to go over this person’s head. Doing it tactfully is not impossible, though there are many wrong ways to approach it. This is where things could quickly escalate into a “Karen” attitude—one that reveals callous entitlement and assumes that the world exists to serve you, in your attempt to summon the force of entrenched power structures to exact revenge over some perceived slight. The employee may get reprimanded by her boss, and may even lose her job, not because the infraction justified it, but because the customer’s show of dissatisfaction was so extreme. So, yeah, don’t be that person.