I think you mean losing. Winston didn't want to love Big Brother, he was tortured into it. The message was a bleak one where the opposition was a hoax and there will be no escape. Orwell went through the Spanish Civil War only to see Franco win and then saw the horrors of WWII, and despite being a very vocal socialist, he already had completely fallen out of love with the soviets and Stalin.

He did not have an optimistic view of the future.

Edit: If you want to see another view of how Orwell saw the future was going, Coming Up for Air was written on the eve of WWII and was a contemporary novel which, while it has a lot of comedy in it, paints a very ominous picture of where he saw the future going. I like to quote this passage because I think it sums up Orwell's whole pessimistic outlook very well.

Behind the bright red counter a girl in a tall white cap was fiddling with an ice-box, and somewhere at the back a radio was playing, plonk-tiddle-tiddle-plonk, a kind of tinny sound. Why the hell am I coming here? I thought to myself as I went in. There’s a kind of atmosphere about these places that gets me down. Everything slick and shiny and streamlined; mirrors, enamel, and chromium plate whichever direction you look in. Everything spent on the decorations and nothing on the food. No real food at all. Just lists of stuff with American names, sort of phantom stuff that you can’t taste and can hardly believe in the existence of. Everything comes out of a carton or a tin, or it’s hauled out of a refrigerator or squirted out of a tap or squeezed out of a tube. No comfort, no privacy. Tall stools to sit on, a kind of narrow ledge to eat off, mirrors all round you. A sort of propaganda floating round, mixed up with the noise of the radio, to the effect that food doesn’t matter, comfort doesn’t matter, nothing matters except slickness and shininess and streamlining. Everything’s streamlined nowadays, even the bullet Hitler’s keeping for you. I ordered a large coffee and a couple of frankfurters. The girl in the white cap jerked them at me with about as much interest as you’d throw ants’ eggs to a goldfish.

Outside the door a newsboy yelled ‘Starnoosstannerd!’ I saw the poster flapping against his knees: LEGS. FRESH DISCOVERIES. Just ‘legs’, you notice. It had got down to that. Two days earlier they’d found a woman’s legs in a railway waiting-room, done up in a brown-paper parcel, and what with successive editions of the papers, the whole nation was supposed to be so passionately interested in these blasted legs that they didn’t need any further introduction. They were the only legs that were news at the moment. It’s queer, I thought, as I ate a bit of roll, how dull the murders are getting nowadays. All this cutting people up and leaving bits of them about the countryside. Not a patch on the old domestic poisoning dramas, Crippen, Seddon, Mrs Maybrick; the truth being, I suppose, that you can’t do a good murder unless you believe you’re going to roast in hell for it.

At this moment I bit into one of my frankfurters, and—Christ!

I can’t honestly say that I’d expected the thing to have a pleasant taste. I’d expected it to taste of nothing, like the roll. But this—well, it was quite an experience. Let me try and describe it to you.

The frankfurter had a rubber skin, of course, and my temporary teeth weren’t much of a fit. I had to do a kind of sawing movement before I could get my teeth through the skin. And then suddenly—pop! The thing burst in my mouth like a rotten pear. A sort of horrible soft stuff was oozing all over my tongue. But the taste! For a moment I just couldn’t believe it. Then I rolled my tongue round it again and had another try. It was fish! A sausage, a thing calling itself a frankfurter, filled with fish! I got up and walked straight out without touching my coffee. God knows what that might have tasted of.