When it comes to people’s final wishes, some choose to keep things simple—while others take the chance to make requests that are strange, shocking, or completely unbelievable. Although most wills follow a standard format, lawyers occasionally come across instructions so bizarre that they leave everyone in the room speechless. From odd demands to wildly unexpected inheritances, attorneys on Reddit shared some of the craziest things clients have tried to include in their wills, and some of these stories are almost too weird to be true.
These Lawyers Couldn’t Believe What Clients Wanted In Their Wills
Love, Not Heritage
One Reddit user shared a heartbreaking story about their grandfather’s final will. Originally, the inheritance meant for his youngest son was supposed to eventually pass down to the grandchild instead. But after being diagnosed with terminal cancer, the grandfather discovered that his son was about to make yet another selfish and reckless decision. Furious and disappointed, he warned him that going through with it would cost him his inheritance entirely. The son ignored the warning anyway. When the will was finally read, the family was stunned by the final sentence addressed to him: “And to my youngest son, I leave only my love.” According to the grandchild, those were the most painful words they had ever heard.
Love, Not Heritage
Tortoise Issues to Come
One Reddit user shared a surprisingly frustrating inheritance story involving their aunt, who, despite them having no real closeness, has named them in her will as the future owner of her tortoise. The tortoise, a sulcata, was originally gotten when the user was a child and showed a brief moment of curiosity, but has since grown into a massive, long-lived animal that could easily outlive them by decades. The user explained that they’ve repeatedly made it clear they do not want the responsibility of caring for it or finding it a new home, but their aunt dismisses the concerns and refuses to change her will. Now, their only hope is that she lives a long life—because the alternative is unexpectedly inheriting a very large, very long-lived tortoise they never wanted.
Tortoise Issues To Come
Uncomfortable Will
One Reddit user shared an uncomfortable experience after being named executor of their grandmother’s will, which also left them the house, its contents, and a portion of a life insurance payout shared with their sister and mother. However, things took a deeply awkward turn because their mother had always mentioned that their father—her husband—would have been happy with just a simple table from the estate. Instead, the will contained a lengthy and harsh paragraph explicitly cutting him out of everything, stating he was to receive nothing, that he should not take anything from the house or estate, and harshly criticizing his character and parenting. It also mentioned that his mother had only reluctantly included the user’s own mother in the will. The user described the situation as emotionally uncomfortable and said it left them dealing with an unexpectedly tense and humiliating family dynamic during an already sensitive process.
Uncomfortable Will
Oddball Heirlooms
One Reddit user shared that after their great aunt—whom they barely knew—passed away, they were surprised to find themselves included in her will, inheriting a taxidermied giant silk moth that had once been displayed on her wall. Apparently, someone had told her about their interest in insects, which inspired the unusual bequest. The user later said they still keep it as part of their collection of odd keepsakes and actually considers it one of their coolest possessions. In a humorous twist, they also learned that another relative was left a Furby, adding to the aunt’s reputation for leaving behind unexpectedly quirky inheritances.
Oddball Heirlooms
Legacy, Sugar, and Spice
One Reddit user recalled two particularly unusual will requests. In the first, a wealthy physician set up a fairly standard trust for his sister and niece, with the remainder intended for a scholarship after their deaths—but the conditions for that scholarship were extremely specific, including requirements such as being a 5’8” redheaded male, having documented ancestry tracing back to the Mayflower, and studying medicine, while explicitly excluding anyone who had studied or practiced chiropractic care. The user noted that it seemed designed to reflect the doctor’s own personal identity and preferences. In a second example, they mentioned a woman who simply requested that “Pour Some Sugar on Me” by Def Leppard be played at her funeral, adding a much lighter and more straightforwardly quirky final wish in contrast to the first.
Legacy, Sugar, And Spice
Ride on forever
One Reddit user who worked on estate planning shared a story about a man living on a reservation who had no immediate family and a strong passion for his Harley. He left most of his assets to the tribe, but also included a very unusual request: he wanted to be buried with his motorcycle, in a riding position, upside down, beneath his favorite stretch of road. Despite careful explanations that such a burial arrangement would be highly impractical, he remained insistent and said his friends already understood and agreed to his wishes, only wanting it formally written into his will. The writer explained they added the clause with several contingencies, though they doubted it would ever be carried out exactly as described. Still, they noted that his riding buddies might honor the spirit of the request in their own way, remembering him as a tough, free-spirited biker with distinctive tattoos.
Ride On Forever
Clause of Rivalry
One Reddit user shared a story about their best friend’s parents, both alumni of Michigan State University, who included a very deliberate clause in their will reflecting the school’s intense rivalry with University of Michigan. The will stated that if any of their children chose to attend the University of Michigan, they would forfeit any financial support for tuition there. The user noted the irony that the family’s lawyer had actually earned his law degree from U of M and was reportedly stunned that such a petty-sounding rivalry condition had been formally included in an otherwise serious legal document.
Clause Of Rivalry
Confusion and Collections
One Reddit user shared a complicated inheritance story involving their father’s will, which divided sentimental possessions in a very specific way—leaving one brother his prized guitar collection, another brother his model airplane collection, while the user and their sister were left out of those personal items entirely. The will did, however, set aside the remaining financial assets for the grandchildren’s education, with a clause stating that any unused funds within a certain timeframe would be donated to hospice care. The user added that things became even more confusing because their father mistakenly believed he controlled a trust asset he did not actually have authority over, which unexpectedly resulted in all siblings receiving some money after all. To make matters more difficult, locating the remaining liquid assets has proven challenging, especially since the trustee—an estranged aunt who reportedly dislikes the family—cannot be found.
Confusion And Collections
A Fearless Legacy
One Reddit user shared a recently passed grandfather’s unusual final request, delivered through a very specific inheritance: a navy blue tie covered in pink elephants. While it looked comically bold, the user’s grandmother explained that he deliberately wore it during business dealings as a psychological tactic—his logic being that someone willing to wear something so ridiculous must be confident, unpredictable, and unconcerned with judgment, which in turn made others uneasy in negotiations. According to the family, he wanted the tie passed down so the same “fearless” mindset could be inherited along with it.
A Fearless Legacy
Housebound Heartbreak
One Reddit user shared a deeply upsetting situation involving their husband’s step-grandfather, who passed away after a period of illness when the family already knew his time was limited. In his will, he included a clause stating that his wife was required to continue living in their current home for the rest of her life and was not allowed to sell it, despite her previously expressing a clear wish to downsize and move closer to her children and grandchildren. The user explained that this effectively prevented her from making the change she had hoped for after more than 30 years of marriage, even though she had contributed to the household in various ways, despite the property being solely in his name. The family was reportedly united in opposition to the arrangement and may challenge it, but the situation left them all shocked and saddened by what felt like a controlling final decision made from beyond the grave.
Housebound Heartbreak
Extra Cash Chaos
One Reddit user shared how being their great-grandmother’s apparent favorite among a huge extended family—roughly five children, 30 grandchildren, and 65 great-grandchildren—ended up creating unexpected awkwardness after her passing. Although there wasn’t much money left due to nursing home costs, the user received about $3,000 more than the rest of the family, which caused tension and jealousy, with one great-aunt reacting as though they had inherited something far more substantial like a luxury estate. To ease the situation and avoid further resentment, the user said they eventually used part of the money to treat around 20 cousins to dinner and drinks during Christmas, trying to turn an uncomfortable inheritance disparity into a shared family experience.
Extra Cash Chaos
Book Bequests
One Reddit user shared a story from their father’s law partner about a client who took inheritance planning to an extremely detailed level. Instead of simply dividing her estate broadly, she insisted on creating a highly specific will that itemized her personal library book by book, assigning each individual title to a designated beneficiary of her choosing. According to the lawyer, the list had grown to around 2,000 books distributed among roughly 30 people, with meticulous instructions for who should receive each one. The most surprising part, the user noted, was that she regularly returned—at least once a year—to update the will and add new books to the ever-expanding list, making her estate planning an ongoing, highly detailed cataloging project.
Book Bequests
Legacy of Rebellion
One Reddit user shared a personal family story about their great-grandfather, who owned a large stretch of land in South Sacramento that he built into wealth by gradually selling off former apple orchards to real estate developers. He had two daughters, and through that line came the user’s family. The user explained that their biological father was rebellious and had a difficult relationship with the family, and shortly before the great-grandfather passed away—when the user’s mother was pregnant with them—he made a final change to his will. Instead of leaving a portion of the inheritance to the user’s father, he arranged for the user to receive $20,000 upon turning 18. The user reflected that, although they never got to meet him, they were grateful for the quiet act of recognition and support from a relative they only know through that final decision.
Legacy Of Rebellion
Roast and Testament
One Reddit user shared that their grandmother’s will was unusually direct and even humorous in tone, openly explaining who would receive—or not receive—certain prized possessions. Rather than quietly distributing assets, the document included blunt, almost “roast-like” commentary, stating why specific family members were being excluded from items such as a gold ring, a car, and a collection of paintings, often tying the decisions to their behavior or reliability. In contrast, one son was explicitly singled out as the sole responsible family member and therefore the only one trusted with an inheritance. The user added that, surprisingly, the grandmother is still alive and had already read the will aloud to the family the previous year, making for an awkward but memorable moment of brutally honest estate planning.
Roast And Testament
Dog’s Legacy Drama
One Reddit user working in heritage management for a bank shared a particularly chaotic will case involving a €6,000 inheritance tied to a dog. The will specified that the money would go to whoever took care of the deceased person’s dog, but there was no clear agreement among the heirs about who that actually was, leading to disputes and confusion. The situation escalated at the bank office, with family members arguing in front of staff while the employee was trying to sort out the issue and seeking clarification from the Reddit user’s department. From the bank’s perspective, nothing could be processed without consensus from the heirs, and there was also no formal way to verify the dog’s current status or caregiving arrangements. The user added that situations like this were not uncommon in their line of work and often led to unexpectedly messy inheritance disputes over seemingly simple conditions.
Dog’s Legacy Drama
Inheritance Twist
One Reddit user shared a difficult but surprisingly calm experience involving their grandfather’s will. Due to dementia, the grandfather mistakenly confused the user with their father, whom he believed had wronged him financially, and ultimately left the user just $1. Meanwhile, the rest of the family received substantial inheritances ranging from $100,000 to several million dollars each. The user noted that although the situation was emotionally complicated, the relatives acknowledged they understood the confusion behind the decision, even if they ultimately accepted their shares. Despite the stark difference in inheritance, the user reflected that it was never their money to begin with and expressed relief that their sister received $100,000, which they felt was genuinely helpful for her situation.
Inheritance Twist
Love Sets Sail
One Reddit user shared a striking final wish in a couple’s will: the wife requested that she and her husband’s ashes be placed on a model yacht decorated with flowers matching her bridal bouquet and wedding colors, and that the vessel be set sail on the anniversary following the surviving spouse’s death, symbolically drifting off into the sunset. However, the instructions went even further, specifying that the ceremony could only take place if the ocean temperature was exactly 80°F, which the user noted was particularly challenging given that they live in the tropics.
Love Sets Sail
Water Clause
One Reddit user shared a surprising discovery made while working for a city during the renovation of a small park that had originally been donated in the 1910s. While reviewing the handwritten deed for restrictions or easements, they found a clause stating that the original family could reclaim the property if it was not “perpetually provided with a fountain of pleasant running water fit for consumption by man and beast alike.” Since the family still had living descendants in the area, the city decided to be cautious and installed a new drinking fountain—complete with a dog bowl feature—to ensure the condition was clearly satisfied and avoid any risk of the land being taken back.
Water Clause
Chocolate Chase Chaos
One Reddit user shared a lighthearted but unexpectedly complicated inheritance story involving their grandfather’s will, which included a seemingly simple gift: a chocolate bar for each grandchild. However, because there were around 12 cousins and a couple of them were difficult to locate, the entire estate settlement ended up being delayed for months while efforts were made to track everyone down. The court even required proof that reasonable attempts had been made to find the missing relatives before the distribution could proceed. The lawyer overseeing the case was reportedly surprised that the will had been drafted in a way that allowed such a small, specific condition to stall a much larger estate. In the end, the user joked that at least they personally benefited from it, receiving a Toblerone as their share of the inheritance.
Chocolate Chase Chaos
Grandma’s Love
One Reddit user shared a deeply personal story about their grandmother’s passing and the unexpected outcome of her will. While most of the family had moved away and rarely visited, the user and their children remained close, regularly spending time with her and sharing weekly meals. During a particularly difficult period after the birth of the user’s youngest child, the grandmother even cooked daily meals to help support them. When she died, it turned out she left her entire estate to the user, including sentimental belongings and even a hidden stash of gold coins buried in her backyard. Although the inheritance caused tension and resentment among other relatives who felt entitled to items, the user reflected that the decision seemed to come from the closeness they had maintained, and that the memories and small personal items from their grandmother meant far more than the material value.
Grandma’s Love
Sounds Fishy
One Reddit user who works as a qualified solicitor shared two of the most unusual will instructions they’ve encountered. In the first case, a woman seriously requested the creation of a £100,000 trust fund for her pet goldfish, specifying that it should be fed fresh avocado daily and cared for after her death by a local dog walker—despite it being an entirely ordinary fish. In the second case, another client revealed she had a secret daughter unknown to the rest of her family, including her husband, and wanted to leave that daughter both money and personal photographs while ensuring the arrangement remained hidden during her lifetime. The solicitor noted both situations as striking examples of how wills can sometimes involve highly unexpected and sensitive revelations.
Sounds Fishy
Outhouse Legacy
One Reddit user shared a story about their great-uncle, who had spent years fighting repeated attempts by a nearby city council to take his land for a water treatment plant under eminent domain. As a final act of defiance, his will left the contents of his outhouse to that same city council. The user explained that, in a humorous follow-up, his children later boxed up the books and magazines stored there and delivered them directly to City Hall as a kind of dark joke.
Outhouse Legacy
Pennies From Purgatory
One Reddit user working with estate cases shared what they described as one of the most impractical wills they had ever encountered. The client had left roughly one-third of his estate to be split among about 30 people decades ago, but by the time the will was being executed, those original beneficiaries had grown into nearly 100 descendants. The user explained that the process became a logistical nightmare, as locating and legally serving all of them for court proceedings took years, especially given that each person was entitled to only a very small share. After eight years of ongoing efforts, the estate was still not fully resolved. The user reflected that, from their perspective, simple lifetime gifting would have avoided a huge amount of legal complexity, delay, and expense for everyone involved.
Pennies From Purgatory
Lotto for the Lost
One Reddit user shared a memorable case from their mother, who works for a lawyer, involving an elderly couple in deteriorating health who came in to finalize their wills and appoint the lawyer as executor of their estate. The couple passed away shortly afterward, leaving their entire estate to various animal charities, as they had no children. However, what made the case unusual was an additional instruction: they had prepaid for a full year of Canadian Lotto 6/49 tickets, with explicit directions that any winnings should also go to the charities named in the will. As a result, the executor—through the law office—was required to regularly check the lottery results twice a week for an entire year after their deaths, just in case any winnings needed to be distributed according to their wishes.
Lotto For The Lost
Renting Revenge Residuals
One Reddit user shared a story they heard while working at an older, affluent hotel that also rented out apartments, involving a long-term tenant who made an unusual decision in his will. Instead of leaving the remainder of his estate to his family, he arranged for it to continue covering the rent on his hotel apartment even after his death. According to the story, this arrangement kept the unit effectively “paid for” for several years until the funds eventually ran out. The user noted that while they couldn’t fully verify the details, they could easily imagine how frustrated his heirs might have been, especially given that the estate effectively continued benefiting the hotel rather than the family.
Renting Revenge Residuals
Generous Surprise Trust
Bank manager here: I had a long-term client with roughly 300–400k placed in a trust, and over time I got to know her quite well. I was genuinely impressed when I learned that the named beneficiaries of the trust were Phoenix Children’s Hospital and the Make-A-Wish Foundation, which made her seem incredibly generous. It wasn’t until she passed away that I discovered she actually had a son. Things became extremely awkward when he came in to process her estate, only for us to issue two large checks to those organizations while he ended up receiving nothing from the trust.
Generous Surprise Trust
Springloaded Coffin
I (early 20s) was required to draft a will because of the health insurance provided through my workplace, and alongside all the sensible legal provisions, the in-house lawyer told me it was perfectly acceptable to include a more unusual clause. It stated that my funeral wishes were to be buried in a coffin fitted with a spring-loaded mechanism designed to startle any future archaeologists who might open it. I also added that if this proved too expensive or impractical, I would instead be cremated and have my ashes scattered in a specific location I had chosen.
Springloaded Coffin
Jackpot of Love
Not exactly a will, but my grandpa left a touching surprise for my grandmother to discover after he passed. While going through his wallet, she found a note that read, “Alyce, look in the envelope in the top drawer of the desk in T’s room. I love you.” When she followed the instructions, she found an envelope filled with years of accumulated lottery winnings and scratch-off tickets, totaling around $9,000. She used to tease him for spending money on them, but in the end, the gesture became something deeply meaningful to her. Now she treasures both the note and the envelope, and the story remains a lasting reminder of how thoughtful he was and how much he loved her.
Jackpot Of Love
Golfing for Redemption
I had a client who was an excellent golfer—seriously, the kind of player who stood out. He ended up having a falling out with his son, who was also quite skilled at the game. Instead of simply cutting him out of the will, he initially planned to leave him $2,000 along with a putter. The condition attached to the money was that it could only be spent on golf lessons. Luckily, the two reconciled before the father passed away, and that particular clause was eventually removed from the estate plan.
Golfing For Redemption
Just Purrfect
Not a lawyer, but an elderly woman my family knew left her large house in an affluent neighborhood, along with her estate, to family friends on the condition that they care for her cats and keep them living in the home for as long as the cats remained alive. Once the cats eventually passed away, the house was to be sold and whatever remained of the estate donated. The unusual part is that it’s now been around 20 years, the cats are still supposedly alive, and, strangely enough, they’ve even “changed color” over time.
Just Purrfect
Ashes and Offspring
A lot of people end up including unusual instructions in their wills, like leaving money to friends or family specifically so they can travel and scatter their ashes around the world, or setting up pet trusts that allocate large sums to ensure a beloved animal is cared for for the rest of its life. One of the more memorable examples I’ve heard of, though not something I personally drafted, involved a lawyer who left the bulk of his estate—worth millions in today’s money—to whichever woman in the Toronto area had the most children at a specified date in the future. If I remember correctly, the winner ultimately had 10 children.
Ashes And Offspring
Family Ties
My great-aunt, who never had children, included a provision in her will stating that after a certain percentage of her money was evenly distributed among her nieces and nephews, whatever remained would go to my dad on the condition that he use it to host a large family reunion. Even after she passed away, she still managed to bring everyone together, and the result was a memorable celebration held in her honor that turned into a genuine family gathering.
Family Ties
Family Coin
When my great-grandad passed away, his will stated that his coin collection was to be divided equally among the family—there were about 8–9 of us and roughly three potato sacks full of coins. We all gathered around a table and simply took turns picking one coin at a time until everything was gone. Among the collection was an Iron Cross, which stood out as particularly unusual, since the only person on that side of the family who had been involved in the war was his father, who served with the ANZACs in World War I.
Family Coin
Picture-Perfect Payback
So many unusual provisions come up in wills. In one case, a daughter clearly on the outs with her mother was left only a photograph, while her two siblings split a multimillion-dollar estate evenly between them. In another, there was a cash bequest specifically earmarked for the care of cats, which was unusual enough that it required a formal memo to explain it to the charitable beneficiaries involved. I’ve also seen instructions directing that all family cookbooks be destroyed. It’s a good reminder that wills become public once probate is opened, which is why some people prefer using a pour-over will that funnels assets into a trust instead, since trust documents remain private and allow for more unconventional instructions without public scrutiny.
Picture Perfect Payback
Charitable Challenge Twist
My dad left me only $100 in his will, while the rest of his $500k estate went to my brother, which honestly felt like a clear betrayal. During the reading, the lawyer came over with a grin and said, “Your dad really loved you,” but I immediately dismissed it—until he pointed out that I hadn’t read the final clause. He circled the last paragraph, and when I looked closer, I realized it said that my brother’s entire inheritance depended on him establishing a charitable foundation in our mother’s name within one year. If he failed to do that, the whole estate would be split equally between the two of us. The twist made it clear my father wasn’t simply favoring one of us—he was trying to push us toward working together and honoring our mother’s legacy, forcing a reconciliation neither of us expected.
Charitable Challenge Twist
Tenant Treasure Trove
When I was in my first year at university, a friend’s landlord passed away and left the house to whoever happened to be living there as tenants at the time. As it turned out, my mate and three other students ended up splitting ownership of the property. It was a pretty incredible windfall for a group of 18-year-olds—the house was likely worth around $400,000 to $500,000 NZD and was located in a typical university suburb where it was usually rented out to groups of four students on yearly leases. The owner was quite elderly and had a real estate agent managing it for about the last 15 years, and apparently the agent was not pleased about how things turned out.
Tenant Treasure Trove
Crumpets for Class
I had an ex-girlfriend whose grandmother had a great sense of humor. She lived in a small, wealthy town where nearly everyone had large houses and expensive cars, and people outside the area automatically assumed anyone from there was well-off. In her will, she specified that she wanted tea and crumpets served at her funeral, and if there was any money left over after that, it should be donated to the less fortunate in the town. The joke, of course, was that there really wasn’t anyone “less fortunate” there—so it came across as her subtle way of poking fun at the community’s wealth and image even after her death.
Crumpets For Class
Riches to Rover
My friend works doing filing and paperwork for a law firm back home, and she told me about a very wealthy woman who wanted to leave a substantial sum specifically for her dog. The arrangement was set up so that $10,000 a month would be used to cover the dog’s care—housing, medical needs, food, and anything else required—until the end of its life. Any funds left over would be donated to an animal shelter. Interestingly, she didn’t leave anything to her family at all, and the dog’s age wasn’t even particularly clear at the time the will was being prepared.
Riches To Rover
Interstellar Inheritance Illusion
My will currently states that my entire life savings is hidden behind a cross-planet scavenger hunt, with the first clue located on a mountain peak on Pluto, sealed inside a container that can only be opened by someone who is biologically related to me. I’m in my early 20s, and my family has a habit of living well past 100, so I fully expect this to become someone else’s problem far in the future. Either way, I secretly hope that one of my great-grandchildren actually goes through the trouble of traveling all the way to Pluto, only to discover that I was never serious in the first place.
Interstellar Inheritance Illusion