“What’s yours is mine, and what’s mine is only mine?” Yeah, money has a funny way of complicating relationships. Whether splitting bills, arguing over who’s paying for dinner, or debating the best way to spend unexpected cash, it’s a guaranteed way to test any couple’s teamwork.

One Redditor recently found himself in a bit of a jackpot jam with his girlfriend when he won $500 in a raffle, but she suggested he buy her shoes, jeans, and a ring.

More info: Reddit

Money can’t buy happiness, but it sure can start an argument

Image credits: Timur Weber / Pexels (not the actual photo)

When one man wins $500 in a raffle, his girlfriend expects to receive half of it or at least a shopping session, despite always criticizing her boyfriend when he gambles

Image credits: Ben Iwara / Unsplash (not the actual photo)

The man pays for 80% of the things in their relationship, while his girlfriend contributes 20% from her parent’s credit card

Image credits: Alexander Mils / Unsplash (not the actual photo)

The man’s girlfriend always complains about his gambling, saying he shouldn’t waste his money on it, but is suddenly pro-gambling after he wins

Image credits: Outside_Locksmith754

The man plays a raffle and hits the jackpot but won’t share his winnings with his girlfriend—who asks him to buy her shoes and jeans—but offers to pay for dinner and drinks instead

The OP (original poster), a 22-year-old guy, was on vacation with his family and his girlfriend when they stumbled upon a local cornhole tournament. But, besides the beanbag-flinging fun, the event featured raffle boards with prizes, including a juicy $500 cash prize.

Feeling lucky, our OP dropped $30 for three tickets, and after a few hours, he hit the jackpot! I don’t know about you, but I’d probably be spending the cash in my head at that point. And so was the OP’s girlfriend.

Instead of cheers and high-fives, he got demands from her. As soon as the $500 landed in his hands, his girlfriend asked the million-dollar question—or, in this case, the $500 question: “Are we splitting this 50/50?” His response? A resounding, “Umm, no, I don’t think so.”

What followed was a string of requests that ranged from new shoes and jeans to a savings account for an engagement ring. When he refused all of those options, he offered to use some of the money to cover drinks and food for the night and take her out to dinner later. Sounds fair, right? Not to her.

But here’s the interesting part: according to the boyfriend, he already covers 80% of their expenses, including dinners and activities. Meanwhile, his girlfriend chips in 20%, but it’s usually on her parents’ dime since she’s a college student with access to their credit card.

Oh, and did I mention she’s usually anti-gambling—except when he wins? She’s apparently all about saving for a ring, but when he loses money on raffles or slots, she’s quick to scold him for “wasting money.”

Image credits: SLNC / Unsplash (not the actual photo)

I get it—money can be a hot-button topic in any relationship, especially when dynamics aren’t equal. The pros say the trick to avoiding blowouts is setting clear expectations early on. For example, who pays for what? Are big purchases a joint decision?

Tackling these questions head-on can save you from awkward disagreements down the line. Communication is everything when it comes to keeping love, wallets, and raffle winnings intact.

Raffle winnings might seem like a small thing, but they can spark bigger conversations about values, expectations, and fairness in a relationship—like a girlfriend hoping for a shopping spree with her boyfriend’s winnings. It’s one thing to hint at a gift, but treating your partner like a personal piggy bank is another story.

Generosity is a beautiful thing, but it can quickly turn sour if it feels one-sided. When someone constantly expects you to foot the bill or treat them, it’s time to hit pause and reevaluate. For instance, if you’re covering dinners, movie nights, and their occasional “just-this-once” shopping sprees, but they always expect and ask for more, it might be a sign that they are using you.

Addressing this starts with a friendly but firm conversation: “I love treating you, but I need to feel like we’re both contributing.” Healthy relationships thrive on reciprocity, not on one partner feeling like an ATM.

A better approach? Celebrate the win together without turning it into a shopping list. After all, a treat shared is way sweeter than one demanded.  And hey, if nothing else, at least the OP offered to buy the drinks that night.

What do you think? Should he have split the winnings, or was he right to keep them? Drop your comments below!

Netizens agree with the man, saying he is not a jerk for refusing to share his winnings with his girlfriend, arguing that her demands were unreasonable

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