Good Job is Slate’s advice column on work. Have a workplace problem big or small? Send it to Laura Helmuth and Doree Shafrir here. It’s anonymous!

Dear Good Job, 

I work in a family law practice. One of my colleagues is a divorce lawyer, and I just found out about an annual prank of hers.

She sends out Valentine’s Day cards to her clients’ exes each year that read, “Guess Who?” I realize this is a bit after the fact, but she was crowing over this at a recent get-together for members of our firm at a bar. I find this to be in extremely poor taste. Should I say something?

—No Need to Rub it In

Dear No Need to Rub It In, 

My Colleague Is a Super Fan of a Very Controversial Franchise. And She’s Forcing It on Us All. I Begged My Boyfriend to Tell Me What He Wants to Try in Bed. Oh God, Anything But This. I Just Saved My Wife From Her Wildly Entitled Sister. But Now She’s Angry at Me! This Content is Available for Slate Plus members only Help! We Had a Special Family Tradition. Then Our Nephew’s New Wife Put a Stop to It.

Your instincts are correct! This is, indeed, in extremely poor taste and something that could backfire spectacularly. My mind immediately goes to a scenario where a client’s ex is unstable, and this little prank turns into something that causes actual physical harm. But even if the worst-case response to her stunt didn’t occur, it’s still tacky and cringeworthy to send these cards. I’m sure your colleague has negotiated some very contentious divorces, but her clients’ exes are still human beings with feelings! I should also say that I am someone who absolutely hates pranks and cannot watch prank shows because I feel horrible for the people being pranked.

That said, I feel no compunction about pranking people in retribution for a prank, so if you want to send some sort of anonymous card to this colleague of yours that will spook her and make her think twice about sending out these valentines going forward—well, I certainly didn’t see you dropping any envelopes off in the mailbox with no return address!

If you don’t share my penchant for retribution, I understand. Jokes aside, I do think you should say something to your colleague. Try: “I don’t know why I was just thinking about it, but do you still send out those Valentine’s Day cards to your clients’ exes? Don’t you worry that if they found out it was you, it would reflect really poorly on the firm?” Hopefully, she takes the hint.

—Doree

Classic Prudie

My husband and I are in our early 40s and have been together about 15 years. We have two kids and a good life. After my father-in-law passed away a couple of years ago, my husband mentioned that we needed to be more diligent about getting our affairs in order—wills, guardianships, etc. I agreed, and we’ve had some discussions about it. I found out today that he bought and paid for a single plot next to his father…