Do you forgot that she kissed Cage romantically and emotional for the goodbye in limo? She sucks!

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You make some good points.
But the one I would disagree with is that Gage WOULD worry himself over it afterwards, at least for a good while.
I think he surprised
himself
by falling in love with Diana. That was never his intention, he wanted to win the contest yes but he didn't seem to plan on truly caring for her.
So in that context, he did lose. Even with all his money he couldn't keep Diana, couldn't make him her true love.
She loved David.
I'd say this cloud is Cumulo Nimbus.
Didn't he discover America?
Penfold, shush.

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Gage won that game. He always wins in life. At everything. Did you not notice the man is super rich? He wins in his career. He wins the affection of beautiful women. And he won her heart also. Its a hobby of Gage's.
No, this is not a love story. Its a story about the game of manipulation by the rich and powerful.
Actually, Gage did not win. He lost. He thought he won by getting Diana to come live with him. She did clearly care for Gage.
But she never loved him, not like she loved David.
Gage saw this clearly at the auction, during the rain scene.
He knew that for all his money & charm, he could never buy Diana.
He lost.
I'd say this cloud is Cumulo Nimbus.
Didn't he discover America?
Penfold, shush.

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Money is power. Even if you're ugly or old , with money you can have any woman you want. It shows in this film too. If Redford wasn't a billionaire I'm sure Demi's character wouldn't have given him the time of day. So money makes him more alluring.

No offense but i really think you missed the point.
The Gage-Diana crush had almost nothing to do with the proposal, because she was positive the 10 millions were nothing to this guy, but when they first met there was a lot of chemistry, and when he told her the story about the girl in the train station, thats when she finally turned down the guard (the story was very meningful).
And why not?, after all David was the one that should have stopped the proposal inmediatly in the pool table, and beep the beep out of Diana at the first sign of doubt in her.
The divorce papers, and the previous hippo purchase where all his leap of fate, his way to say: I totally beep up everything, this is me, trully loving you, nothing really means something to me but you!!it was a very touching scene, he didnt expect anythinghe only showed her his true love.

Lol you missed it then.she did choose her ex over Gage, in the limo, before the "million dollar club" story from Gage, she tells him "we need to talk", meaning she was about to break up with him. And Gage didn't MAKE her do anything, she went back to Woody because she wanted toGage didn't force her against her will to go back to her ex, that was all her. And the end scene on the pier confirms that.

No, Gage suspected they where still deeply in love, and confirmed it during the rain scene.
After that in the limo, she wanted to speak him (clearly about going back to David), you can see clearly he was waiting for that, the million dollar club was only his noble friendly way to easy up the split.

What's worse is that, in the end, she didn't even chose her ex over Gage, Gage pretty much made her go back with him! In the end, I just wasn't convinced anymore that she actually loved him all that much.

I never thought she actually fell in love with him at allwhich was the whole point in the end when he told her to go back, more or less.
"I'd like to confuse bok choy with cabbage, sir."

I'm sorry but none of that interests me. What I am interested in is what conversation this plot inspired with your husband do tell?
Exactly, because that's the reason for the film's commercial appealthe watercooler factor.
I'm not sure what the OP expected to see in the second half of the film. Perhaps she was looking forward to seeing David and Diana playing happy families and completing their dream house.

"I'd like to confuse bok choy with cabbage, sir."

I'm sorry but none of that interests me. What I am interested in is what conversation this plot inspired with your husband do tell?