“If you don’t ask, you don’t get.” simple right? It’s something my dad would say when he would try and get some type of discount or better seat than he paid for. I’ve found it to be true throughout my entire life, however.
An example of this would be yesterday evening I had a flight from Austin to Atlanta with Southwest. When you fly Southwest there are no assigned seats you just take one that's open. So I was boarding and saw that an entire row at the very front, what would be first class on other airlines, was still available. Twice as much leg room and a window seat. A good 60 people had already walked by it assuming you had to pay more to sit there. I saw it, asked the attendant if it was open, and took it. The guy behind said he heard me asking and snagged the aisle seat as well.
That’s a small example, but this has played out in just asking cashiers if they have student discounts or just want to give one to me anyway. Usually, if you aren’t a jerk they’ll give one to you just because. Sometimes they don’t, but what did you lose? The respect of the cashier and everyone around you? Chump change.
The key is to just ask. Just get the words out instead of living in wonder and what if. My friend was buying an iMac for his job and it was about to be a few thousand dollars. His co-worker was ready to buy it when my friend asked if they could get that price down a bit. The guy took off $500. $500 they were literally about to pay out of pocket is now back in their pocket. All it took was a question.
Just ask for that date, promotion, or upgrade. What do you have to lose? Your life will stay exactly the same if you are told no. So it can only get better if you are told yes.