Dear Prudence is Slate’s advice column. Submit questions here.

Dear Prudence,

My husband and I went on vacation for a week recently and left his brother, “John,” to housesit since he’d been going through some difficulty in his marriage.

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We returned to find our liquor supply exhausted and an expensive down pillow from our bed had been … let’s call it “ravaged” and was beyond cleaning. John admitted to consuming our booze and replaced it, but never mentioned anything about ruining the pillow when I asked him if there was anything else he needed to replace. My husband says John is going through a lot right now and that we should look the other way in terms of the pillow. That pillow was over $400! I think if someone destroys property, they must either replace it or pay for it, even if they weren’t in their right mind when they ruined it. Should I insist that my brother-in-law compensate us for it?

—Sister-in-law of a Pillow Perv

Dear Sister-in-law,

I wish I could go back in time and encourage you to remove the $400 pillow from your bed before his visit. But here we are.

It’s worth asking—to be clear, not insisting but asking—him if he’d be willing to replace the pillow: “Hey John, one more thing we noticed after your visit. The pillow from your bed is damaged beyond repair and needs to be replaced. Would you mind covering that?”

If he won’t, let it go. This isn’t your sink, refrigerator, or something essential. I’m not confident that someone who thought it was OK to drink all of your liquor is stable or reasonable enough right now to say, “Of course,” and Venmo you. And it’s not worth ruining the relationship over this. Consider this a $400 lesson that not everyone is qualified to be your house sitter.

Classic Prudie

I have been seeing a really sweet guy for three months. He is intelligent, fun, considerate, and generous. My issue is that he is a virgin and doesn’t seem very interested in changing that. We are both in our early 30s. I am recently divorced—my husband was a compulsive cheat—and have a 2-year-old son. I have discussed sex with “James” and he said that he originally wanted to wait until marriage for religious reasons, but now doesn’t feel that is necessary, he just wants it to be with the right person.