My (18M) friend (19F) gambled with my money and won. Does she keep it?

Friendship and money—two elements that rarely mix well without clear boundaries. When an 18-year-old left his computer unlocked with a gambling site open, he returned to find his female friend had won $50 using his account. Rather than being upset, he doubled down, instructing her to continue gambling until they reached nearly $800. The celebration quickly soured when she expected a share of the winnings.

What started as a casual afternoon among friends transformed into a tense standoff over gambling profits and unspoken expectations. The young man, confident in his position that the money belonged solely to him, was met with his friend’s disappointed exit and a brewing conflict that left him questioning the unwritten rules of friendship when money enters the equation.

‘My (18M) friend (19F) gambled with my money and won. Does she keep it?’

“In scenarios involving money between friends, assumptions are relationship killers,” says Dr. Marisa Franco, friendship expert and author of “Platonic: How the Science of Attachment Can Help You Make—and Keep—Friends.” “Explicit communication about expectations is crucial, especially when financial risk is involved.”

The core conflict stems from different perspectives: the account owner sees himself as the sole risk-taker since it’s his money, while his friend views her participation as a contribution deserving compensation. Research from the Journal of Economic Psychology confirms this pattern—people providing capital typically feel entitled to all profits, while those providing labor expect proportional compensation.

As relationship counselor Esther Perel suggests, “Clarity is kindness. Ambiguity is actually cruel.” A healthier approach would be establishing clear terms before gambling occurs. By discussing what happens in both winning and losing scenarios upfront, both parties could engage with aligned expectations and avoid the emotional fallout that often results when money and friendship intersect.

These are the responses from Reddit users:

Here are some hot takes from the Reddit community – candid and sometimes brutally honest!

These are popular opinions on Reddit, but do they really reflect what you’d do in real life?

When friendship meets finances, clear rules prevent misunderstandings. This case shows how important it is to establish expectations before money enters the equation. The wisest approach? Agree on terms upfront – whether sharing a percentage or keeping all winnings with the account owner.

What would you do in this situation? Share the winnings or keep them? Have you ever had money complicate a friendship?