August 10, 2026 at 10:35 am

His Landlord Won’t Cash His Rent Checks—So He’s Considering Paying Next Month in $20 Bills

by Heather Hall

Man counting his rent money

Pexels

Paying rent shouldn’t feel like a guessing game.

Unfortunately, that’s exactly what it’s been for this tenant because his landlord waits weeks to deposit his rent checks. When this happens, it leaves him wondering when the money will finally disappear from his bank account.

Well, this time, after another month went by without the previous check getting cashed, he finally decided to change his payment method.

Rather than writing a check, he decided to pay his $900 rent in twenty-dollar bills to get his landlord’s attention.

The only problem is that now he’s wondering if it would be going to far or if there’s a better way to handle it.

Read on for his full story.

Is it unreasonable to shove my rent in 20’s in an envelope and pay it that way?

So my rent is due when I wake up this morning. It’s $900, and my landlord doesn’t have any kind of e-pay option, so I pay by check.

I handed over my check for the month of May at the end of April. He still hasn’t deposited it.

My June rent is due today, and he still hasn’t deposited the check from the month that’s ending.

To avoid multiple checks going out at once, he came up with a new plan.

I don’t want two payments coming out at the same time on some unspecified date because I have no idea when he’s actually going to go to the bank.

The whole element of uncertainty with my checking account is driving me up a wall and making me angry. So I took $500 out of one account and $400 out of another, separated all the $20 bills, and shoved them into a manila envelope, which I intend to drop off tomorrow.

Am I being a jerk? Or is this a reasonable expression of dissent over the fact that he still hasn’t deposited my other check?

Eek! It’s easy to see why he’s so stressed over this, but there was probably an easier way to handle it.

Let’s check out what the folks over at Reddit think he should do.

This reader suggests using money orders.

Rent Money 3 His Landlord Won’t Cash His Rent Checks—So He’s Considering Paying Next Month in $20 Bills

Here’s another fan of money orders.

Rent Money 2 His Landlord Won’t Cash His Rent Checks—So He’s Considering Paying Next Month in $20 Bills

For this reader, the best option is a cashier’s check from the bank.

Rent Money 1 His Landlord Won’t Cash His Rent Checks—So He’s Considering Paying Next Month in $20 Bills

If you enjoyed this post, check out this story about a student who did the math and figured out he was better off skipping school than serving detention if he forgot his ID.

Here’s a fantastic idea.

Rent Money His Landlord Won’t Cash His Rent Checks—So He’s Considering Paying Next Month in $20 Bills

He needs to proceed with caution.

Paying rent in cash may feel satisfying in the moment, but it could easily create a bigger headache if something goes wrong.

However, if he decides to use cash anyway, he should never hand it over without getting a signed receipt. That’s the only way to protect himself if there’s ever a dispute.

A better long-term solution may be opening a separate bank account just for rent. Then the money stays safe and the landlord can cash the check whenever he finally decides to make the trip to the bank.

Enjoyed this story?

Readers who liked this also read this story about a group of friends who were denied a townhome lease because they’re not considered a “family.”
Read Story

Heather Hall | Contributing Writer, Life & Drama

Heather Hall is a contributing writer for TwistedSifter specializing in internet culture, workplace conflict, and viral customer service stories. With over a decade of editorial experience in digital publishing, Heather excels at curating trending online discussions and providing insightful commentary on the daily dramas that capture the internet's attention.

Since beginning her career in 2011, she has developed deep expertise in SEO-driven digital content, having written for a wide array of publications covering lifestyle, business, and travel. At TwistedSifter, Heather focuses on synthesizing complex social media threads into engaging, highly readable narratives that highlight the human element of viral news.

When she isn’t analyzing the latest internet discourse, Heather is a dedicated mother of three sons who takes family gaming nights entirely too seriously—whether she is dominating in Mario Kart, exploring The Legend of Zelda, or jumping into Roblox.

Connect with Heather on Facebook and LinkedIn.