Overly Generous Fool

Generosity is generally a good thing, but like all good qualities, there is a limit. Some people are so generous that they allow it to ruin their finances. They might be bad with money, have a hard time saying no, easily manipulated, desperate to be liked, extremely compassionate, or some combination of the above. Naturally, these character's habits will lead them to various financial woes, such as debt, overdue bills, poverty, etc.

Naturally, these people are magnets for people who would seek to exploit their generosity, such as Gold Diggers, False Friends, Fair Weather Friends, Fair Weather Foes, Lazy Bums, etc. These people don't need to try very hard to convince an overly generous person to give them money and will have no problem ditching their money tree if they go broke or stops being a doormat. The generous person's true friends naturally won't take advantage of them and will try to help them learn to be smarter with their finances, teach them to not allow people to exploit them, or try to drive the moochers away.

Sub-Trope of Extreme Doormat, Money Dumb, and Stupid Good. Someone who believes that Virtue Is Weakness likely sees every generous person as this. If the character takes someone on a shopping spree or out to a fancy restaurant and fails to take into account how much money that they are spending, expect them to be met with a Shockingly Expensive Bill. If the people they give money to tell lies about needing it, they are likely to be a Horrible Judge of Character and/or Super Gullible. Characters who suffer from Chronic Hero Syndrome are likely to have this problem. Compare A Fool and His New Money Are Soon Parted. Contrast Greed Makes You Dumb, when a character loses money because of their Greed.

Examples

Anime & Manga

• Assassination Classroom: The principal and owner of the Wakaba Park Nursery, Matsukata, is mentioned to have a soft spot for kids who are stuck on the primary school waiting list and happily takes them in despite the negative effect on his finances. He doesn't mind much, but it means that he lacks the money to fix his rickety, fragile building. It provides the perfect opportunity for Class 3-E to help make amends after accidentally injuring him.
• Fruits Basket: After Yuki and Kyo get frustrated that Tohru used most of her earnings from her job to buy ingredients to make Valentine's Day chocolates instead of paying her deposit for the school trip, wishing she wouldn't be "an idiot", Momiji tells them a story he heard in class called "The Foolish Traveler", about a young man who keeps giving away his belongings to greedy passersby when they ask for help. The Traveler gives the clothes off his back, his money, and eventually his body parts until he has nothing left but a head. When a monster asks for his eyes and he obliges, the monster cruelly leaves him a slip of paper calling him a fool. Momiji, however, deconstructs this, arguing the traveler was not foolish but simply chose not to fret about loss or hardship and instead wanting to give and make others happy, whether they deserve it or not. The fault is on the passersby for not appreciating this. He does this to evoke a parallel to Tohru's kindness so that Yuki and Kyo will show their appreciation instead of thinking her foolish.
• Great Teacher Onizuka: Zig-Zagged. When Onizuka accidentally spends the school's field trip money, he manages to convince the school not to fire him, but only by pledging an even more expensive field trip which he can't possibly afford. He then fails to earn anything near the amount needed, only to win a brand new Mercedes Benz in an unrelated lottery that he can sell for the money he needs. He then gives the car to a down-on-his-luck stranger to use as collateral to prevent the bank from seizing his company, with no guarantees that the stranger will return it on time, if ever. The stranger then turns out to be a conman hired by the person trying to frame Onizuka in the first place, but then it turns out the "conman" was actually telling the truth and returns the Mercedes once he got the money he needed.
• One Piece: Baby 5 is an Extreme Doormat in general due to her unwillingness to say no to any request. One of the consequences of this behavior is that she's in debt because she's always giving away money to people who ask.

Comic Strips

• Spider-Man: Justified during one arc where Mary Jane becomes obsessed with an evangelist running a drive for charity donations and begins donating more than the Parkers can afford. The evangelist is a fraudster using airborne drugs to make his audiences suggestible.

Films — Live-Action

• Alluded to in Batman Begins, when Alfred tells Bruce that his father Thomas almost bankrupted his corporation, Wayne Enterprises, trying to stimulate Gotham City's economy and save it from economic collapse.
• Enchanted: When Robert prepares to send Giselle away, he gives her some money—only to see her immediately give it all away to a homeless old woman who said she needed it more. This prompts Robert to stick with Giselle a little longer, as he realizes that she genuinely doesn't know how the "real world" operates as opposed to her fairy tale home of Andalasia.
• It's a Wonderful Life: George Bailey's father Peter was a generous man who founded Bailey Building and Loan so he could help the residents of Bedford Falls obtain housing. However, it's noted by George himself that his father "was no businessman" and his insistence on helping people even if it was bad for business was often the root of the Building and Loan's financial problems under his leadership.

Literature

• In Meg Cabot's No Words, Jo's father is facing financial difficulties in his old age due to his habit of bailing his friends out of jams by lending money that isn't paid back. Jo's trying to help him, but he's reluctant to accept that help out of pride.
• A Song of Ice and Fire: Tytos Lannister was an extremely generous man who almost ruined his house by constantly dropping the debts people owed him. He did this out of a desire to be loved, but he was viewed as a softhearted fool by both the other lords and his subjects.
• The White Company: Sir Nigel's squire Alleyne is put in charge of his lord's purse by his wife. He doesn't understand why until he sees that Nigel is such a paragon of chivalry he'd cheerfully give their travel funds to beggars without a thought as to the rest of the trip. When Nigel tells him to give a beggar the purse, Alleyne discreetly gives the man a single coin so they can keep going.

Live-Action TV

• Better Call Saul: Convenience store owner Charles McGill Sr. refused to see the bad in anybody and was also generous to a fault, giving money to anyone in need — which made him an easy mark for every scammer with a sob story, despite the warnings of his son Jimmy. After getting a speech from one such grifter about "wolves and sheep", and seeing that his father was never going to change, Jimmy gave up and began Stealing from the Till, which Charles simply refused to believe when his older son, Chuck, tried to warn him. Between this and the scammers, Charles' store was eventually driven to bankruptcy and he died six months later, while Jimmy entered a downward spiral that led to him becoming a professional Con Man and, eventually, Amoral Attorney Saul Goodman.
• Community: In Intermediate Documentary Filmmaking, Britta offers to give LeVar Burton all of the money in her checking account, leading to him describing her as "a good friend, but really stupid with her money".
• Played for Laughs in the Doctor Who 60th Anniversary Special "The Star Beast". In the time between her last appearance and now, Donna Noble had been able to win ₤166 million from the lottery and, thanks to subtle subconscious nudges from her repressed memories of the Doctor, bought a new house then gave away her winnings as that was what she thought he would do. When she regained her memories, the first thing she did was ream out the Doctor for unwittingly making her do that.
• In Family Law (2021), Bryan Beasley, the mail-delivery guy for the Svensson & Svensson offices, is one of the most generous characters on the show. This gets him in a lot of trouble in "A River in Egypt", where he's conned by his new fiancee and loses almost everything because she convinced him to put almost all of his property jointly in their names.

Manhua

• Played for Laughs in one Old Master Q strip. Master Q is walking to his girlfriend's place on a date when he comes across an alley filled with beggars. He gives money to each and every one of them, until reaching the last beggar when Old Master Q realizes he's out of cash. Cue the last panel depicting Master Q arriving at his girlfriend's place in boxers.

Music

• The final verse of "In the Jailhouse Now" details how the singer ended up in jail; he fell in love with a girl and spent all his money taking her to every show.

Tabletop Games

• Ars Magica: Under the Point Build System, characters can have "Generous" as a minor or major Flaw, depending on just how indiscriminately they give up their possessions to others. As a Personality Flaw, it isn't framed as a necessarily negative trait, but as a story hook to get them into unexpected situations.

Theatre

• Urinetown: In contrast to her father's cruel, tightfisted rules on the public bathroom fees, Hope Cladwell in the end takes power over the Urine Good Company and allows the people to pee for free, wherever and whenever (and with whomever) they wish. Due to the continuing water shortage, however, this causes what remains of the water to become polluted, causing the people to instead die slow, painful deaths; she is implied to get executed by the very people she tried to help.
• Timon of Athens is very free and easy with his money but after he goes broke, his Fair Weather Friends ditch him, causing him to Madden Into Misanthropy.

Video Games

• Genshin Impact: Kaveh is a very generous individual and always wants to do the right thing, but this has caused him such financial distress that he has to live with Alhaitham, and the two are very much Teyvat's Odd Couple.

Western Animation

• Ducktales 1987: The episode "Dr. Jekyll and Mr McDuck" has a potion that turns people into this; Dr. Jekyll invented the potion in order to give himself a more likeable personality. It worked, but the catch is that it made whoever was sprayed with it generous to the point of giving away all of their money, and a villain planned on using it to effectively force people to give him their money.
• Family Guy: In "Bookie of the Year", Frank Sinatra Jr. opens a restaurant in Quahog, but it's floundering because of his overly generous nature, including paying the customers' tabs. But when Brian and Stewie finally convince him to cut it out, the townspeople reject the restaurant because they've come to expect free food.
• The Simpsons: In "Dumbbell Indemnity", Moe falls in love with a woman who actually likes him back. Unable to believe his luck and terrified that she'll leave him if he doesn't keep making grand gestures, Moe ends up badly in debt and enlists Homer's help for an insurance fraud scheme that naturally goes wrong, resulting in Homer going to jail.
• SpongeBob SquarePants: "Krusty Love" is about Mr. Krabs falling in love with Mrs. Puff, and to show his affection, he tries to give her as many gifts as he can, which is very out of character for such a tightwad. It's only after he spends $100,000 at a fancy dinner that he realizes just how much he's spending. The next day, Mr. Krabs has SpongeBob accompany him on his next date with Puff to prevent him from spending anymore. It doesn't work, and Krabs repeatedly forces SpongeBob to buy things for her, despite his many objections. It's quite telling just how bad the situation is when SpongeBob ultimately snaps, lets out a gibberish version of a Cluster Bleep-Bomb, and just leaves Krabs to his own devices. Thankfully, the episode ends with Puff gently telling Krabs that she doesn't need all of these gifts and that it's probably best if they just go Dutch.

---