Can I Tell My Friend Her Halloween Costume Is Problematic?

A new friend in the Midwest was invited to an outdoor Halloween party where mask-wearing was requested. We went shopping for an art-inspired costume for her. But I saw that she was gravitating toward period costumes. After the party, she posted pictures online. I was stunned! She wore a full-blown Scarlett O’Hara-type gown — to a mansion, no less! If I’d known, I would have tried to talk her out if it. This year’s widespread Black Lives Matter protests, along with the traditional whitewashing of the antebellum South, make her choice seem insensitive. I’ll be seeing her soon, and I already feel awkward. I know she’ll share details of the party, and I feel obligated to enlighten her. Any advice?

FRIEND

It’s one thing if your friend went to the party dressed as Scarlett O’Hara. Casually masquerading as the heroine of a racist novel and film in which Black people are portrayed as happy slaves is problematic. Costume parties don’t offer enough context for racial commentary.

But it’s another thing if your friend simply rented a Victorian dress with a crinoline underneath to make the skirt poof out. That style originated in England and became fashionable in many places (with ever larger hoop skirts) in the mid-19th century. The dresses are not primarily associated slavery or the South. Women in the North wore them, too.

So, which was she: dressed as a character, or from an era? Be careful about jumping to racism. (Your desire to “enlighten” your friend sounds condescending.) If you’re not sure, ask her: “What was your Halloween costume?” If she says Scarlett, ask if she considered the racial implications. If not, save your energy for clear-cut instances of racism.

Dying Wish

I broke up with my boyfriend during our coronavirus quarantine. Recently, he was diagnosed with inoperable lung cancer. He begged me not to let him die alone. So I now have frequent video chats with him, accompany him to doctors’ appointments and even stayed overnight in the hospital with him after he was admitted for pneumonia. The problem: He thinks we’re back together again and wants to resume our sex life (which his doctor blessed). I don’t have those feelings for him anymore, but I don’t want to hurt him, either. Should I have mercy sex with him or tell him I’m not into him?

ANONYMOUS

Neither! By your kind behavior, you’ve shown that you’re a good and loyal friend to your ex. Tell him you want to continue supporting him during this challenging period, but you haven’t changed your mind about the breakup.

Now, this may hurt his feelings or even make him angry with you. Give him time to work through his emotions, but don’t sleep with him out of pity. If I were in your ex’s position, I would value a great friend more than a lover who was only acting the part. Wouldn’t you?

Puppy Problems

During the pandemic, our three kids convinced us to adopt a puppy from our local animal shelter. Spoiler alert: Raising a puppy is much harder than we thought. And ours is destructive. We’re considering returning him to the shelter, but we feel guilty about it and our kids don’t want us to. What should we do?

H.G.

I think you feel guilty about returning the puppy to the shelter because you should. When you adopted him, you made a commitment to the dog, the shelter and your family to provide a good home for him. Going back on your promise too easily would be bad for everyone.

Call the shelter and tell the adoption coordinator that you’re having real trouble with the puppy and need help. The shelter may offer assistance or connect you with a trainer. I know that raising a puppy is hard work. But until you’ve tried your best, it would be wrong to return him. (And depending on the shelter, doing so may have deadly consequences for the puppy.)

Follow-Up Q

I am the sister of the man who wrote to you last week, wanting to take back a now valuable photograph from our parents’ estate because he gave it to them many years ago. He was right when he said his siblings objected, but neither he nor you explored why that is. My sister devoted untold hours to taking care of our parents. And I gave them substantial financial help to allow them to stay in their home. Our brother was mostly missing in action. Additional thoughts now?

GRACE

I’m glad you wrote. Family situations are almost always more complex than a single anecdote can convey. That’s why I try not to judge anyone and suggested that your brother leave the photograph in your parents’ estate.

But now that I have you, let me encourage you to sit down with your siblings (when it’s safe to do that) and get beyond this conflict. You’ve all suffered a big loss with the death of your parents, and your support for each other may be much more valuable than any Eggleston photograph. (And I love Eggleston!) It’s just stuff.

For help with your awkward situation, send a question to SocialQ@nytimes.com, to Philip Galanes on Facebook or @SocialQPhilip on Twitter.