Dear Prudence

Help! There Are Unmistakable Signs My Best Friend Is a Jerk.

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

A woman is partially visible and appears annoyed. A gift box is shown in collage at right.
Photo illustration by Slate. Photo by master1305/iStock/Getty Images Plus. 

Dear Prudence,
I have had a best friend for over a decade. He is fabulously gay, in his 50s, has a house in an expensive city and a vacation home on the coast, and we have been through a lot together. I thought we were extremely close; we would talk almost daily.

I got married in November, and since it was going to be a tiny COVID wedding, my then-fiancé and I decided to only invite family. My best friend said it would kill him not to be there, so I fought with my now-husband to have my best friend and his husband come to a family-only event. My best friend showed up to the wedding, without his husband, who had RSVP’d and we had also paid for. We also paid for my best friend’s hotel room. He never explained why his rude husband ditched the RSVP last-minute, even though I’ve asked him, and he never got us a wedding gift.


Now, I am due with our first baby, and I have my baby registry up. While I didn’t have a full baby shower, I did have a small “sprinkle.” I sent a link to our registry letting people know that we would have a real celebration once it was safe to do so. My “bestie” never even got us a tiny baby toy off the registry, even though he calls himself our baby’s “uncle.” He fawns over the phone asking if he can visit as soon as the baby is born, and I can’t help but feel a little resentful of his lack of generosity and overall cheapness. I have always bought dinners or gifts for him and his family, sent bottles of sparkling for birthdays or big events, and recently bought him a really generous housewarming gift.


He is not under any financial hardship, and I can’t help but feel upset at his lack of manners and consideration. I feel myself involuntarily pulling away and distancing myself. I know I shouldn’t “expect” a gift or any generosity, but honestly, I can’t help but feel like this behavior is totally rude. How do I keep resentment from destroying our “best friend” relationship? Am I being completely unreasonable?

—Upset and Very Pregnant

I’m torn! What kind of best friend doesn’t send a gift for his best friend’s baby? BUT ALSO, what kind of best friend lets relatively mild faux pas ruin a friendship? If this gentleman truly is important to you, I would urge you to focus less on how he handles social obligations and more on what is actually important about the friendship. Do you still talk on the phone? Will he visit the new baby, and how doting and wonderful an uncle will he be? I can think of any number of perfectly reasonable explanations for his wedding and sprinkle behavior, but I also think that even if he was simply rude or absent-minded, those don’t qualify as reasons to “destroy” your decade-plus relationship. Extend this guy a little grace in what, for all you know, has been as bad a year for him as it has been a momentous one for you. You’re likely to find it repaid and more as your new family life goes on.

–Prudie, generously