The Matters w/ Matt: Parking Lot Lifeguard

Every Wednesday: I never fail to be disgusted with advice columns. I am unsure why they still get paid to do what they do. As always, I am in awe when it comes to awful examples like Dear Prudence and Dear Abby. The columnists seem to get rewarded for giving you bad advice. I think that people get terrible advice from them. I don’t blame anyone that calls advice column responses garbage. I use my postings to correct these responses and help society by being an utmost asshole, (as always, a hat tip to Aaron Clarey at Asshole Consulting).

Consider this piece from Dear Annie’s column (courtesy of Arcamax) from April 27, 2022:

Dear (Matters):

Thank you for the wise advice that you give to your readers. I have often taken your advice and applied it to my situation in life. But this is a new issue for me.

A dear friend of mine died a couple of years ago (not of COVID-19). She faced death pragmatically and fearlessly. Having managed the at-home care of her parents when they were in failing health, using paid caregivers, she told me she had directed her brother to sell her condo and donate the proceeds to a charity that helps families by providing subsidies to keep unhealthy adults in their own homes.

I recently learned that her brother is renting out that condo instead of selling it as she wished. Perhaps he has made a donation to his sister’s chosen charity from other sources of money and has honored his sister’s wishes in that way. Perhaps he is ignoring her wishes.

Do you think I should dare to ask my friend’s brother why my friend’s condo is being rented and not sold? I risk losing a friendly relationship with that man and his wife, who I also know and see more often. They may not know why my friend ever mentioned the matter to me. I certainly have no proof of her conversation with me.

Loyalty to my friend and to her intentions for her “estate” is my only motivation. I have thought of asking the charity if they have received any money after my friend’s death. The condo was worth hundreds of thousands, and my friend said she was happy to donate that much because if her parents had lingered longer, the funds for them would have run out. But I do not know the name of the charitable organization that she intended to give the money to.

Please help me discern the right thing to do here. 

—– Quandary

Dear Quandary:

The road to hell is often paved with good intentions. It is especially malicious when you rent a steamroller for the road crew.

I think that you mean well with your actions, but in the long run, you are just getting in the way.

It makes more sense to let the family handle their business. The only way that I would suggest getting involved is if you had a legal reason to do so or if someone is in danger. If this doesn’t apply; butt out.

Instead of sticking your nose in business that isn’t yours, tell your friend that you are there for them. I would even suggest doing smaller things to be supportive, outside of another good intentioned bad follow through thing like sending flowers. Use your brain and find a way to help; not stir pots.

It is okay to do something small like pick up a paper, but to interject with large assumptions is risky. Please think of this in the future and continue to be a friend of those in need.


I don’t imagine that I will have a shortage of emails to answer. I would love to start doing this for anyone that sends me an email. If this is you; email us at

If you hate advice columns; I don’t blame you. If it isn’t soft people giving advice; it is someone trying to justify acting like an insensitive asshole. Till next week.


About freemattpodcast

Lead shill for The FreeMatt Podcast
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1 Response to The Matters w/ Matt: Parking Lot Lifeguard

  1. Pingback: FreeMatt in Review: 4-25 to 4-29 (2022) | Mogadishu Matt

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