From Dathus, Tales From Retail:
This happened a few years ago at a gas station I used to work the night shift at. We have the usual amenities: Cigarettes, lottery machine, scratch tickets. This gentleman came up to me at a little after midnight, and purchased some scratch tickets.
Now, the OLG has the saying "know your limit; play within it" in their commercials and posted everywhere on their stuff at my work. I never stop customers because hey, I'm not your dad. This guy starts with dropping about $40 on tickets ranging from $3 to $5. No big deal, pretty typical. He goes to our little side counter to scratch and do his thing while I restock the tickets he purchased.
Three to five minutes later, he comes back with a mitt full of losing tickets. "I need to win my money back".
Now, I'm the type of person who gets off a little bit on people screwing themselves over, so I had an inward smile as I pulled out the tickets again. "Sure, sir. Let's see if you can do so!" Another $50 into my till, and back he goes.
Repeat this until he spends an easy $200 on tickets, winning back maybe $75-150 of it. MAYBE $150, I'm pretty sure he didn't break $100, but that was years ago. I did warn him after the second trip back, though, that he should "play for fun, not to win".
Poor guy just smiled and kept trying. I felt a little bad, but in the same vein, it's not my money. He was also a regular who would drop $50-100 about every week for a few months on tickets. I stopped seeing him after a while, but my co-workers mentioned him now and again, so he was still chasing the big win.
I did feel a little bad for the guy, though. Scratch tickets are(usually) money sinks, and not a way to win it big.