Why is Hollywood so afraid of men being shorter than women?

Because it creates a less stressful and less hostile environment for everyone involved. The compliment wasn't mean spirited.

she's way too old for him

I do agree that compliments based on anything physical are retarded. You can't change your height. Maybe this guy didn't mean it as a compliment. I want to assume the whole conversation was staged but it's not the case 100% of the time.