What could Jeannie ever see in Randall?

Yes he is a bit of a caricature, but his whole family are horribly naff so I can imagine all of those rotten genetics could quite possibly create someone like him.

I think their relationship works because Randall tolerates Jeannie's obnoxious, self-centred tantrums; he may be a berk but he's right under her thumb.

http://www.hawkensian.com/

My theory - because Randall is the exact opposite of her father.

Randall is happy go lucky and makes her the center of his life. Warren was all business and pushed her aside.

Simple. He is not her father.

Randall is far less attractive, has a pedestrian retail job, and comes from a Bohemian lifestyle with far less than privilege than her father offered her.

Women tend to be hypergamous in nature, and do not tend to pair downward.

I think he was probably the best she could do at that point, because of her age. It was either Randall or permanent spinsterhood.

"I am always happy to engage in POLITE discourse."

Randall's at least as attractive as Jeanie. And he's nice, and not an A Grade bitca (I know Jeannie was grieving, so we may not have seen her true self). So there's that.

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https://www.youtube.com/watch?v=Qssvnjj5Moo

I think you're right that they may have cranked up the "loser-ness" of Randall a bit beyond reason. I don't know that it's a major criticism. The movie is supposed to be funny, and going a bit too far is one of the basic forms of screen humor. I don't think he was really on the nose, so much as humorously exaggerated. Also, you get a bit of a pass with making a character extreme if he's not onscreen for a ton of minutes.

Jeannie was not intended to be highly attractive. It's a general characteristic of the world in which movies take place, I think, that you have to recalibrate your standards of attractiveness from those that apply in the real world. In the film world, an ugly woman is beautiful woman wearing glasses. I think the hair/makeup/lighting people cranked Hope Davis' looks down a bit from how she appears in other movies around the same time (e.g., say, "Proof" or "Next Stop Wonderland).

Also - aside from physically - she really isn't very attractive. She's short-tempered, self-centered and irritating. She's not particularly successful. Although her family background is relatively privileged, I don't think she'd quite qualify as an "heiress," nor does she seem to have taken much away from whatever advantageous education she presumably got.

What I took away was that she recognized Randall's shortcomings, but understood that he was the best she was going to do. She may have had some suppressed frustration over that, which contributed to her response to Schmidt's attempt to un-suppress it.

The "he's not her father" response seems to be pretty meaningless to me, for what that's worth.

Jeannie is no prize pig herself.

She's a woman of average appearance, approaching 40, and in spite of her upper middle class background she has a dead-end job as a shipping clerk. On top of that, she's an ill-tempered, nagging little brat who most men wouldn't want to put up with unless they themselves were desperate. So Randall isn't really a big step down for her, it isn't as though a dashing young CEO of a fortune 500 company was about to sweep Jeannie off her feet.

"Hypergamous".... Wow, that 's a new word for me. Using a man to move up in socioeconomic status.