AITA for making my girlfriend’s son give me his gambling winnings?

The neon lights of the casino buzzed, but the real sparks flew in a hotel room nearby. A 44-year-old man, chilling with his girlfriend’s 18-year-old son during a summer trip, handed him $100 to try his luck on the casino floor. When the teen strutted back with a cool $1,100, pride turned to shock as the man claimed the winnings as “communal.” The teen’s fury lit up the night, turning a fun stop into a family feud.

Caught between fairness and authority, the man’s move left the teen feeling robbed. Readers can sense the sting—who deserves the cash when the stakes were set so casually? This tale of casino wins, blurred boundaries, and a teen’s trust dives into a messy clash of expectations in a blended family.

‘AITA for making my girlfriend’s son give me his gambling winnings?’

On a summer trip with his girlfriend and her son, the Reddit user faced a heated fallout over a casino windfall. Here’s his story:

I (44m) have been with my girlfriend (40f) for several years now. She has one child--a son who recently turned 18. He and I get along really well, at least for the most part. But recently he and I had our first blowout fight and I'm wondering if I was wrong. What happened was that we were returning home from a summer trip.

My girlfriend decided that we should stop at a casino near the border of our home state--she enjoys gambling, maybe a little too much but that's a different post. We ended up getting a hotel room at the casino for a night. For a lot of it my girlfriend's son and I just hung out and watched a CSI marathon. But eventually we ended up joining his mom on the casino floor.

I gave the boy $100 and told him that he should go make me some money. Eventually I met up with my girlfriend (his mother) and he came up a little later to both of us with a cash waiver for about $1,100. He looked really proud of his earnings. I told him to turn his cash for another $100 but he responded 'No, I think I'll keep this.'

I answered him 'No, you didn't earn that' and took the money and explained that all winnings between us were communal. I gave him another $100. I think that he had no claim to his gambling winnings in the first place since it came from my money.

My girlfriend is actually with me on this. But her son is really mad it me right now; probably the angriest he has ever been, feeling like I stole his winnings and it's had me thinking that maybe I'm in the wrong.

Casinos thrive on chance, but this man’s grab for a teen’s winnings was a sure bet for drama. Giving the 18-year-old $100 to gamble was risky enough, but claiming his $1,100 haul as “communal” crossed a line. The teen’s effort—however lucky—earned the cash, and the man’s retroactive rule smells like a power play. The girlfriend’s support raises questions about fairness in their blended family dynamic.

Gambling’s allure can blur ethical lines. A 2022 study by the National Council on Problem Gambling found 10% of young adults show signs of gambling issues, often encouraged by family (source). The man’s nudge toward gambling, followed by taking the winnings, risks modeling unhealthy behavior.

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Psychologist Dr. John Gottman notes, “Trust in families hinges on fairness and clear communication” (source). The man’s vague “communal” claim after the fact broke trust. He should return the full $1,100, apologizing for the mix-up, and set clear expectations in the future.

The man could discuss house rules with his girlfriend and her son to align on financial boundaries.

Take a look at the comments from fellow users:

Reddit’s rolling the dice with some fiery takes, and they’re not holding back. Here’s what the crowd had to say:

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WavesnMountains − YTA you GAVE the $100 to the kid with no expectation stated to pay it back. It wasn’t a loan, and even if it was, he’s a f**king kid and you should know better. You have no rights to money you gave away.

MabelPines_ − YTA. Yeah it’s your money, but he was the one who went out there made it into more money. He should just give you $100 back and keep the rest.

jg700 − YTA wow you really are TA!

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BeautifulOutside646 − YTA, dude. “Go make me some money” clearly sounds like a joke, especially coming from an adult figure your girlfriend’s son has known for several years and probably liked and respected until now. The best you could have asked for from him was $100 without being an ass.

agetawaycat − YTA! Once you give someone money it belongs to them! You have absolutely no right to steal his money, and I strongly suggest you give it all back to him!

DMPC1234 − YTA, and you know it! You gave him that money thinking he would lose it, and when he didn’t, you took what he made. You suck.

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[Reddit User] − Your logic makes no sense and you’re acting like a complete AH over $1,100. If he won money on a scratch off you gave him, would you make him share that too?. Give him his winnings back, or you will remain YTA.

SpecialProcess5585 − YTA.. You are a thief. The end. If he worked a job and earned the money.. would you take that? Or if he took a hundred dollars and invested it..and now the investment is making money? His work won that money. Maybe.. possibly.. you might have claim to the original hundred dollars back. But whatever he gets with the money.. he did it his self.. Give the kid his money back.

AggravatingPatient18 − YTA You and your GF are ok with stealing money from a kid.. Way to go.

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WebbieVanderquack − YTA. I answered him 'No, you didn't earn that' and took the money and explained that all winnings between us were communal. You can't make a condition after giving someone money, so the winnings are his.

You even acknowledge they're his in the title of your post. Even if you had made it clear that the winnings were 'communal' you'd owe him half that money. You also suck for encouraging your GF's 18-year-old son to gamble, especially when his mother appears to have a gambling problem.
These Reddit opinions hit harder than a jackpot, but do they cash out the truth? Was the man’s move a fair split or a straight-up heist?

This casino caper shows how fast a fun bet can turn into a family bust-up. The man’s claim on the teen’s winnings feels like a bait-and-switch, leaving trust in the dust. Should he have let the kid keep his haul or was splitting it fair game? How would you handle a surprise windfall in a blended family? Toss your thoughts into the pot below—let’s deal with this drama!

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