No-win situation

Rob: Hello and welcome to The English We Speak. I'm Rob.
Li: And hello I'm Li.
Rob: Shh shh Li—quiet please! I need to concentrate, the race is about to finish and I've got a bet on.
Rob: Yeah! I've won. I've actually won. I'm rich!
Li: Well done Rob. So what have you won Rob?
Rob: Ten pounds!
Li: Oh just ten pounds. Ah well, that's quite useful actually.
Rob: Is it. Why is that?
Li: Well, you owe me five pounds and you did say you would buy me a glass of champagne if you won a race.
Rob: Oh right, did I? So, that will leave me with ...  fifty pence. Maybe I'm not a winner after all. Honestly! Every time I make some money I have to give it away.
Li: Sorry Rob, it's a no-win situation or a lose-lose situation. Rob, you can't gain any money because you'll always lose it on something else.
Rob: So even though I did win something, I have also lost. That's a no-win situation is it?
Li: I'm afraid it is. A no-win situation is one in which a favourable outcome is impossible. You are bound to lose whatever you do. You can also use this phrase to describe situations that aren't just to do with money, like this:
I can get the bus or train to work—either way I'm going to be late. It's a no-win situation.
The cafe only served ham or beef sandwiches but as a vegetarian I was in a no-win situation.
Li: So a no-win situation is one that is certain to end in failure and disappointment. So Rob I can see you are disappointed because you have spent your winnings on me.
Rob: I am. It seems impossible to win money just for myself.
Li: Actually I also won some money—fifty pounds—so I'll buy you a drink, in fact I'll buy you something to eat too and you don't need to pay me back that five pounds.
Rob: Really? Oh Li that's very kind of you. Now I'm in a win-win situation!
Li: Yes, the opposite of a no-win situation is a win-win situation. This is where there is a favourable outcome for everyone involved. Like this:
The house buyer got a good price and the seller was happy to sell quickly so it was a win-win situation.
If I get to invest your money in the company and you get to share the profits, it's a win-win situation.
Rob: So, in a win-win situation everyone is happy! Just like our situation now. So, where are you taking me for dinner Li?
Li: Did I say dinner? I was just going to buy you a sandwich.
Rob: Oh. That's not such a good win-win situation, is it?
Li: Maybe I'll buy you some chips too!
Rob: OK great. Let's go. Bye.
Li: Bye bye.