Good luck. I fly almost every month, and over the last 4 or 5 years I've been upgraded once, and I ask all the time. Airlines are getting more and more strict about upgrades, some going as far as threatening flight attendants with their jobs if they do it.
I have another buddy that flys a lot, and he told me to always ask the gay male attendant when you get on the flight, because the women are usually biyatches. Also ask the lady at check in to put you on a stand by list for first class as well, depending on the airline some will do it.
I'd also keep your eyes open on craigslist for upgrade passes, they pop up on there every once in a while.
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