
You’d think this is obvious advice, but apparently it needs to be said. You should not use AI to write a condolence card, email, or text to your friend. Why? Not only is it poor manners, it’s a disingenuous expression of your feelings.
A condolence note written by AI is a combination of all the information that has ever been fed into the beast of artificial intelligence to help you imitate what a human might say to another human to express sympathy and camaraderie in a time of grief.
Your human version of a personal note to a grieving friend does not need to be complicated or ground-breaking. It just needs to be heartfelt. And your friend can probably tell the difference. This is true for birthday cards and all the things you write to your friends.
Let’s just be human a little while longer. PLEASE!
Why am I bringing up this random etiquette tip?
Other than my own personal disdain for the creep of AI into all written words, the bigger reason is I had the MOST DELIGHTFUL guest on Dear Nina this week.
I sat down with fifth-generation etiquette expert Daniel Post Senning of The Emily Post Institute to explore how classic (and modern!) manners can strengthen and even rescue our adult friendships.
Dan answered several question from members of my Facebook group. In addition to one about an AI-written condolence note, we discussed:
Using etiquette for group chat issues
RSVP blunders
Office friendship confusion (Check out Dan’s new book with his cousin, Lizzie Post, Emily Post’s Business Etiquette)
Bringing up friends’ kids’ posts you see on social media
Cocktail party escapes
Staying friends when your kids’ friendship falters
Friendship breakups
AND MORE!
You don’t want to miss this one!

FIND EPISODE #148 on Apple, Spotify, YouTube, and anywhere you listen to podcasts!
REMINDER: The 2025 friendship challenge is for everyone!
You can start the 2025 challenge any time. Each month is meant to stand alone and you don’t need an entire month to accomplish any of them. Find all the challenges listed here. Come back and let me know how it went no matter when you try that month’s “assignment.”
CHICAGO READERS/LISTENERS—SAVE THE DATE!
I’m doing a live Dear Nina episode in Highland Park, IL on July 31st around 5-7pm. Details and a ticket link are still in the planning phase, but put it on your calendar if you’re in that area or traveling there this summer. I’d love to meet you!
Articles and Other Finds About Friendship
I see so many friendship-related things, either because I find them myself or listeners send them to me. I love hearing from listeners and readers!
I contributed to a piece by Emine Saner in The Guardian this week called “Drifting away from your friends? Here are 10 questions to bring you closer.”
Some homework for you! I’m interviewing the director/producer team of the Netflix documentary, Join or Die. (You can also watch it on the site.) It’s a great film about the history of clubs and organizations in America and why they matter so much to democracy, community, and friendship. You’ll enjoy the Dear Nina episode about it even more if you’ve seen the film.
Books, Shows, Recipes I’m Into These Days
Reading: I’m listening to the newest novel by Abby Jimenez, Say You’ll Remember Me. I’m re-reading Margaret Atwood’s sequel to The Handmaid’s Tale— The Testaments—even though I read it in 2019. I do not remember a thing.
My (mostly) updated 2025 reading list.
TV: I gasped at the season finale of THE LAST OF US. I’m always on high alert and in full anxiety watching that show. I loved episode 9 of THE HANDMAID’S TALE, but found the series finale disappointing and boring. I don’t want to reveal any plot points yet. I know many people still need to watch.
Cooking: Hanging on by a thread over here with all the action in May, including child #2 graduating from high school next week. So no special cooking to report!
Two anonymous friendship advice questions you might have missed
Let’s connect outside of this newsletter: You can find me most often in the Facebook group, Dear Nina: The Group. All the social media links are below. I know I need to get rid of some them!
Instagram | TikTok | YouTube | LinkedIn | Threads | Twitter | Bluesky | My Website
Links to Amazon, Bookshop.org, or other affiliates might earn me a tiny commission, which helps operations of Dear Nina.
For real on the condolence note and so many other things. The AI creep into all sorts of writing is so frustrating.