Originally Posted by
bisonrav
The UK psychology about asking for something is fascinating, and mostly revolves around balancing two divergent aspects: (1) the embarrassment potential of a possible refusal, against (2) someone else getting something you don't. Hence the thinly veiled hostility even to the idea of asking for an upgrade: in doing so the asker is normalizing the requests to the point where in order to avoid missing out it becomes necessary to risk embarrassing refusal oneself.
For a slightly more American perspective on this topic, the following book is pretty good. It even has a chapter on airline upgrades (though clearly pre-DUT). In a nut-shell, you need to ask in a way that makes the other person want to help you.
Never Split the Difference: Negotiating as If Your Life Depended on It