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.

He willingly gave you the money to gamble making that a gift.   With that gift you struck it rich.

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.

If the pot is big enough to fill out the tax paperwork, then the decision tree kicks in, and the answer is it depends.

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.  

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.  

.... 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.

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.

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

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