As long as you were the one playing, the moment he paid, it was your money. I do, however, agree with some others in that showing gratitude the same way a provider would for any other gift. How that’s done is completely up to you and by no means a requirement.
I’m curious what both gentlemen and ladies think about this one.
A while back, I had a lovely dinner date at a casino restaurant. After dinner, on the way back to the suite, we stopped to gamble for a little bit. He was an absolute gentleman... paid for me to play, said he just wanted to watch, talk, and enjoy the moment.
Well… we didn’t play very long before “our” winnings were suddenly more than the date itself. We cashed out, laughed about it, and headed upstairs for champagne.
So now I’m curious…
If a gentleman pays for the lady to play during a date, and she wins big, what do you think is the graceful etiquette?
Does she keep the winnings because they came from her hand/luck?
Does he keep them because he put up the money?
Do they split it?
Does it become part of the magic of the date or the donation?
I have my own thoughts, but I’d love to hear yours.
What would you have done?
He willingly gave you the money to gamble making that a gift. With that gift you struck it rich.
That money is yours.
But if you decide to make it up to him somehow with an in-kind gift of your own, if for no other reason than to balance out the karmic equation, then I don't see any reason not to do so.
What that gift may be I'll leave up to our collective imagination.
My last casino date I won & he paid me to play. When you cash out that's yours to keep it's a bonus. Did he not give you your winnings? Please elaborate. Inquiring minds want to know.
LMAO I offered to split it, he insisted I keep all of it, I "forgot about the clock" that night...
-- Modified on 6/14/2026 12:49:48 AM
If the pot is big enough to fill out the tax paperwork, then the decision tree kicks in, and the answer is it depends.
Anything less, you should enjoy your winnings.
But I agree with Mr Fisher. It is just common courtesy to show the man some gratitude. Do you know what he likes? Is he a cigar man? Does he have a fave bottle of Bourbon? Maybe a gift card to his favorite steakhouse? You know him best.
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But just something that just says "thank you" would more than suffice, but if I were him, I wouldnt have any expectations as again, its yours to keep imo.
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And if you want to throw a few dollars my way in the process, you go right on ahead girl! Sharing is caring. lol.
As long as you were the one playing, the moment he paid, it was your money. I do, however, agree with some others in that showing gratitude the same way a provider would for any other gift. How that’s done is completely up to you and by no means a requirement.
In your case, I would definitely say “ it’s your winning, enjoy”. I would NEVER ask for anything back.
But I hope for this one time, you would have thrown away the clock and maybe if both of you were having a good time then just hang out little longer.I’m not saying to spend the night ,but just… don’t be that clock watcher.
But this is what I’ve done with young ladies and casino play. I’ll start her out and whatever she wins is her’s no doubt.
But I’ve been In situations where the young lady watches me play, and if.. and this is a huge if ..I should win, I’ll give her half of what I won. Just for being that lucky eye candy. I Consider it a “tip”.
But a guy should NEVER get tipped.,😂
Great question with plenty of answers that I'm curious to see the results.
My take - is that he gave you the money to gamble as you see fit - clearly a gift. You're entitled to 100% of it.
On the other hand if I had been given this gift to use and hit a decent amount, I'd have offered to split it 50/50 based upon "he just wanted to watch, talk, and enjoy the moment".
As a gentleman in this situation, I'd have refused the 50% and the moment would be complete.
Unless he gave you the initial stake with a specific agreement that you do something other than keep it all (i.e.: you will split any winnings), there is no need to give him any of your cash bounty. Of course, he's there for other types of your "bounty", lol.
You may want to at least, give him the original stake money back as a polite gesture. Or perhaps extend his time upstairs if desired. But that's a situational decision and entirely up to you and how you feel you want to treat that client.
If there is a next time, keep in mind that this could have gone sour in a hurry. Let's say he gives you $500, ostensibly to gamble, and you lose it all. A bad actor might try to claim that was your fee for the evening, and it was your decision to "piss it away" at the tables. Now he insists on his time upstairs and won't pay any more for the pleasure. That got awkward fast!
If you have casino dates in the future and a similar situation arises, perhaps it's a good idea for you to bring up the topic of how to deal with any winnings?
Life is good
The Cat
.... relayed the story of how, during dinner, the client said they would go gamble and he'd give her some money to do so. They sat down at a table and he pulled out some money and put it in front of him but did not give her any. So she reached into her purse, used her own money and went on to win $2,600.
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Typically, her MO is to share half of the winnings if the client ponies up the money. But since he didn't, she didn't!
I tell her she gets a bonus if I win. Never had anyone complain about it. If she did I wouldn’t see her again. I’m the client.
In my opinion, you should have offered him the original stake back, and you should keep all of the profits. Most guys will say 'that's ok, keep it all', but by offering you look generous and polite and most likely make a good impression. Even better if he says you can keep it all.
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And I agree with Happy, if he does say 'keep it all' it would be courteous of you to quietly extend the date in response to his generosity (how long you extend is solely up to you). You'll probably wind up with a repeat customer.
I've had many Casino dates, and said situation
indeed has thrice occurred.
Me being one to be very grateful for the date,
and enhancement of a thrill of playing with someone else's cash, I felt truly, it wasn't my winnings. (I don't gamble on my own accord)
They all declined to take back the gift, as they're
generosity prevailed.
Simply, they enjoyed the delight of my happiness
and the surge of mutual exhilaration...
Which of course translated into my extra excitement and attentiveness in the boudoir!
Let's be real...$$$$ is an excellent motivator;
Unless one has grown up in it, has never had to
work to survive from an early age and relishes
in the throes of a "trust fund" from generational wealth...
Generally
these types are not, from my experience, much concerned at all about money, nor motivated by
it because there's no anxiety over ever being
destitute.
Angelina Jones
I do think it is probably more a case of "read the room" to see what type of reaction the guy was having. Sure, if he gave the stake as a gift and just wanted to see you playing he's clearly not setting any explicit terms on the winnings and thinking he has no thoughts of sharing is reasonable.
Still, whenever things change so will some aspects of peoples thinking. You hit big, 5 or 6 figures walking away. Keeping it all seems a bit greedy, or a bit selfish and ungrateful in someways. Some guys may still say, yeah that's a lot of money but nothing out of my pocket so why be envious of the good luck. Others might think, if not for me she never would have gotten that so a "thank you" back generous act would be expected.
But, regardless of the actual events both get an additional insight to the person they are with at the time. Never seems to hurt to be generous when the cost is basically zero. Karma and all that. But that goes for both side IMO.
A gentleman does not want the cash back. He does not want to split the winnings. What a gentleman wants is a show of appreciation that goes beyond reimbursement. Throw away the clock. A note of appreciation after the date letting him know how you enjoyed your winnings, perhaps you bought yourself something nice…a gentleman would love to hear that you treated yourself