A split image showing a private message exchange on the left, asking for a better deal, and on the right, an online listing for a 15-by-30-foot above-ground pool in a backyard, which has not been operational for years.
via Canva

Sure, there’s being mindfully frugal. Then, there’s being outright aggressively picky. If you’re someone who by whatever life circumstances has found yourself in a place that’s significantly financially limited, it really pays to be as open as possible to whatever kinds of healthy generosity are being offered your way. At least that’s my hot take. To try and negotiate over an act of generosity just seems to fit more within the lane of self sabotaging than anything else.

1. So, half off the free price seems pretty agreeable

A message thread showing an inquiry from Jim asking for an incentive to accept a free armchair, followed by a reply offering to lower the price by half.
u/furr/via Reddit.com

2. Mutual Aid, Minimal Fiber

choosingbeggars / via reddit.com

Groceries request: cola, candy cereals, and Chobani Flips—needs list reads like a vending machine.

3. Furnish My House & Deliver

choosingbeggars / via reddit.com

Sofa, table, chairs, plus free moving service, because apparently the truck is included.

4. Just Moved In, Now Hand Over Your Entertainment

choosingbeggars / via reddit.com

“Any extra TV, DVD player, or game console ASAP?” New room, instant living room.

5. Pay Me to Take My Pool

choosingbeggars / via reddit.com

It’s cracked, you disassemble, you haul, and there’s a “negotiable” removal fee. A summer project and a bill.

6. $7 an Hour, 98 Hours a Week

choosingbeggars / via reddit.com

Trash compactor pro wanted: two years’ experience and a time-turner.

7. GoFundMe for Pixie Dust

choosingbeggars / via reddit.com

“Help make our Disney trip magical” crowdfunding the souvenir aisle.

8. Free Game, Fast Attitude

choosingbeggars / via reddit.com

Asked for a comp copy; two days later: “I do not appreciate my patience being tested”. Speedrun to entitlement.

9. Free Antiques, But You Deliver to Me

choosingbeggars / via reddit.com

“Won’t spend gas or three hours to pick up your free furniture”. The couch is free; the commute isn’t.

10. Full-Time Childcare, Part-Time Pay

choosingbeggars / via reddit.com

40 hours a week for $250; big responsibilities, tiny budget.

11. DJ Needed: Budget = Vibes

choosingbeggars / via reddit.com

“Large speakers or a free DJ for our event”. Payment in applause and exposure to… sound.

12. It’s My Birthday; Cash Only (No Books)

choosingbeggars / via reddit.com

“Prove the world isn’t awful with gift cards, please”. Literature politely excused.

13. Wedding Photo Booth, Paid in Publicity

choosingbeggar / via reddit.com

“Anyone starting out willing to do it free? We can interview you!”. Exposure package with vows.

14. Free Housing, Prime Miami Only

choosingbeggas / via reddit.com

Aspiring DJ seeks three months rent-free in the nicest neighborhoods, plus light chores.

15. Free Laptop? Not Gaming-Ready, Then Pass

choosingbeggars / via reddit.com

Explore more humorous content:

If these high-pressure bargains gave you secondhand sticker shock, you’ll love a few more deep dives into internet-era comedy like these 20 People Who Refused to be Honest Online, or these 25 Humorous Signs That Were Discovered Amidst Roaming. You can also enjoy this one 15 Competitions People Took Way Too Seriously in the 20th Century.

Meet the Writer

Matt has spent over the last 8 years as both a writer and editor, working in Seattle and Brooklyn, where he is now based. He loves escaping the tirelessly fast pace of the “Mad Apple” that is NYC by taking walks and runs through parks where he’s able to catch up on the latest tea about society from the city’s ever chatty, always hungry, occasionally maniacal, pigeons. They always have a lot to say. When he’s not taking his urban nature strolls, or dutifully combing the deepest rabbit holes of the internet to find the content that’s worth sinking your mind’s teeth into, he’s likely holed up at a dark-lit dive bar with a new book and/or some friends, or just as easily he could be on the hunt for the next addition to his steadily growing plant family.

These days Matt’s caught up in trying to provide folks as many vivid glimpses into the days long since passed as he can, through fun and engaging collections of hand-picked vintage photos.