Some people are just lucky. They seem to get all the perks and upgrades everywhere they go.
Actually, complimentary upgrades rarely happen: it mostly happen to VIPs, friends and family of VIPs, and really very famous people. For those who are lucky enough, the situation must be quite extraordinary for the a business (airline, hotels) to agree to an upgrade.
Trust me, I know. I’ve tried asking a few times myself. Never has it been successful. I did however, do a little research, and found this article in the New York Times that has some good advice for those who would like to try.
“Even if you don’t have the clout of a big agent or an impressive frequent-flier account, you can still improve your chances of better treatment with a few tips from travel pros”, stated the article, and listed some of the tricks in the trade, including asking politely, looking your best and being able to surprise them.
Alternatively, you can try to get an upgraded option for cheaper. Airlines and hotels sometimes will offer cheaper upgrades at the time when you check in if they are in need to fill seats/rooms. “You’ll never know how much it will cost to get an upgrade unless you ask… so ask! You might be surprised”, writes the BBC travel article: How to book a better hotel room.
Let me know how you go!