81 Hilarious And Tragic Examples Of People Trying Way Too Hard To Save A Penny

A friend (Tim) years back. Five of us went to dinner. The young lady that waited on us was 7+ months pregnant. That day had been particularly hard for her. She took our order. Food came. Her service was impeccable. We (friends) left her a great tip. We got up to leave, and I noticed Tim went back to the table. Watched him pick up the tip money, and replace it with $1.00. I went ballistic. The other guys did too. Made him go back into the place, apologize and hand the young lady her full tip. I never invited Tim to another event. Disgusting….

My son has a landscaping business and does jobs for all income levels. If a middle class or lower income person feels like the estimate is too much they will do it in stages or just not hire him. Upper class people will agree to a price then complain about the price, pay VERY late or try to bargain down the price they already agreed on. It’s bizarre.

My roommate in college. He sat myself and the other roommate down when we were all moving out (post graduation). After living together for close to 2 years, splitting groceries, utilities, rent, etc he presented us with an itemized list of every small expense he had incurred or even items he had shared. Sodas. Beer runs. Gas when he drove somewhere. Bags of chips. Pages and pages of one-offs. The thing that got me was that it was all one sided transactions (what we owed him). His position was that it was our responsibility to account for every skittle we let him eat from our bags…

It was like $1700 of just nonsense. He had never mentioned this ledger before. It was wild. Me and the other roommate but said “absolutely not” and that was it. Basically the end of the friendship, too. Very strange.

My grandmother was worth a few million. When I saw her using a toothpick I asked if she had another. She offered me the dry half of the toothpick she was currently using.

BONUS: She had a whole jar of toothpicks and they were stolen from Howard Johnson's.

A rich kid, son of a lawyer, asked me to reimburse him for a banana I ate at his house. It was a shared house with many roommates that I was very close with. I, the poor kid, frequently brought over food and booze to share! I laughed it off but he was serious.

My coworker. I have so many stories.
During the height of Covid, many stores were giving out free Covid kits. Each kit had 5 tests. She and her husband would go to these stores every single day to get a free box each. They did this for months, even though these kits would eventually expire. They must have at least 100 or more.

One day my coworker said she was mad at her daughter because she was showing symptoms of Covid and asked her for test. She didn’t want to give her own daughter one single free test because she didn’t want to waste it. What else are you going to do with it?

And no she never sold any because she’s not that type. She stills has them on her basement.

I’m realizing this might not be a good cheapness story but more a weird coworker story 🤣.

My brother is extremely cheap. He had one job where he traveled for work on his company’s dime. And yet he would still eat food off of other people’s room service trays in the hallway. Yuck.

My grandparents had money. They had a house on cape cod, a house in Naples FL, and would travel around the world multiple times per year. They went to Italy at least once a year.

My grandmother loved an early bird special. She loved her coupons. She lived thru the great depression and you could tell.

Sometimes she'd drag us to olive garden with her coupons, and she'd have us all get a free taster glass of wine. It's just a splash in a glass, barely anything. But then we'd all have to pour it into her glass so she'd have a free full glass with dinner.

😭😭😭 Grandma noooooo. I'll just buy you a glass of wine. But she was so insistent on us doing that.

While wearing a real mink coat. Please.

My friends parents. Dad was a nuclear engineer designing submarines, mom was a tenured physics professor. At a sleepover we were allowed exactly 4oz of orange juice at breakfast. They also split two ply toilet paper to make two rolls, and recycled dryer lint to use in stuffed animals to sell at craft fairs. Now I never really cared but they were not poor. It was just… odd.

Stepdad was super cheap. My mom (5’6”) had cancer. She was very, very ill and her stomach was so full of fluid she couldn’t wear her pants. I was talking to her about what size and color sweats she wanted from Walmart and he LOST his mind, even though I was buying them for her. Ran and grabbed a pair of his (6’2”) old ratty sweats, tossed them at her and told her to wear them. She said they were too big so he grabbed them, held them up to her and said we’re going to cut them off right here then. It took everything I had to not punch him in the face.

An old guy, who was one of the highest paid employees, would bring a bottle of ketchup and an bottle of mustard from his fridge for potlucks. That was his contribution. He would bag up leftovers to take home along with his bottle of ketchup and his bottle of mustard. The secretary told him to at least bring a bag of chips or he would not be welcome to the next potluck. He threw a fit. At subsequent potlucks, he would bring a small bag of chips about the size you would get out of a vending machine, along with his bottle of ketchup and his bottle of mustard.

I don't think anyone ever opened his bag of chips because the same bag showed up at each potluck. I think people might have used his ketchup and mustard. I never did.

My grandfather is worth a few million. His reading glasses broke last week and he said a new $30 pair at CVS is too expensive so he’s opted to stop reading.

Had a roommate lock toilet paper inside a chest and you had to pay him by the square to borrow some. He would also weigh his shampoo after other people showered to ensure no one was using his stuff without paying 💀.

I will never forget my loser neighbor bringing a Tupperware container to a wedding reception to take home food from the buffet….

My grandparents were pretty well off, but my grandmother still used a hair brush with like 4 teeth left and a hand towel so thin, I could see through it. I bought her a new brush and new hand towels, and teased her about squeezing a penny till it was worth $0.10. I miss that woman fiercely.

I had a buddy eric in highschool who was born into a rich home but was always such a cheapskate. At one point our friend group of like 6 people went to McDonalds together. Everyone ordered something except him. He said he was hungry but didnt buy anything. I took this as him meaning he didnt have money. I offered to buy him a meal and he accepted. After he ate the meal he said he was still hungry and ordered something else. I said "hey i thought you didnt have money?" He said "no, I just didnt want to pay" and continued ordering his meal. Never went out with him again after that.

My uncle. He is a cautionary tale.

Basically he never wanted to spend money on ANYONE not even himself (well from time to time lol) he had four kids tho mind you.

One of the stories ive been told is he took my cousins to disneyland and because he didnt want to pay for tickets, made them stand up outside of the entrance and took photos of them. Thats it…the kids never got to see disneyland just stayed outside. And they had the money.


Well he is diabetic and nowadays he lost both his legs and one arm, he still refuses to hire a nurse or some help. He forces his early 20s daughter to care for him and because she is caring for him she cannot have her own income but a tiny amount he gives her every week and still my uncle tells her she is not allowed to use the toilet paper or the food he buys, she has to get her own stuff with the little money she has.

I knew a millionaire who owns a landscaping business, the dude was banned from multiple 7 elevens for filling up his coffee cup with free soda every morning.

My aunt's boyfriend. He washes his car under the pouring rain to not pay water. Once I saw him eating whole shrimp (including the head and the hard shell) to "not waste". He wasn't the one paying for the shrimps.

This mf has nearly half a milion saved because he's so cheap.

A friend who reuses dental floss. Not even once — multiple times. He keeps it draped over the bathroom mirror "to dry." I no longer accept invitations to stay at his place.