Dear Prudence

Help! My Friend Can’t Keep a Job. Should I Tell Her That Her Personality Is the Problem?

Dear Prudence answers more of your questions—only for Slate Plus members.

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Every week, Daniel Mallory Ortberg answers additional questions from readers, just for Slate Plus members.

Q. Friend’s personality: “Mary” is having trouble finding a tech job after years off. She has been reduced to working low-level service jobs, but she keeps getting fired. She says it’s because those jobs are beneath her, but I think the reason is her personality. From what she’s said, it sounds like she was fired for telling her employers all the things they did wrong. I think this is holding her back, in interviews, too. Recently, at a restaurant, she berated the waiter, telling him repeatedly he was deboning the fish incorrectly. She told another waiter they probably didn’t make some obscure coffee drink she wanted because “you probably don’t have very good coffee.” I told her the restaurant behavior embarrassed me, but she’s not connecting the dots. When can you tell a friend their behavior is hampering them?

A: I might tell her, although in this case I think you should be prepared to be either ignored or cut off, given Mary’s track record of listening to criticism. If she’s been fired multiple times and still thinks it’s simply because she’s “too good” for all of these jobs, then my guess is that she’ll dismiss you as, at best, misguided or naïve when it comes to the world of tech, or, at worst, somehow jealous or hoping that she’ll fail. But given that this behavior bleeds over to how she treats service workers in public, and that it’s embarrassed you personally, I think you should talk to her frankly. (I’d be mortified if someone I was getting dinner with started berating a waiter over fish. It’s one thing to ask for something specific and quite another to start laying into someone.) Be as kind as you can, but not at the expense of clarity, and be prepared for her initial reaction to be a bad one. If you want to simply stick to how she treats waitstaff in public, that’s fine. If you want to see if there’s any chance you can help her out of the hole she’s dug herself, ask her if she’s willing to hear your thoughts and advice about her attempts to break back into the tech industry. If she says, “No,” then you can back off, but I hope she might consider listening to a friend when she’s refused to listen to what multiple employers in a row have tried to say.