Three reasons to avoid saying the phrase "Wish me luck!" as part of your goodbye dialogue:
It's aggressive, presumptuous, and authoritarian.
You're not even asking someone to wish you luck. You're telling them to offer you the wish. You're practically ordering them to do it. It's at least a little audacious, if not downright pushy.
Is there any other instance in which one person tells another person exactly what to say as they part? Can you even imagine it?
"Tell me not to worry!"
"Say something positive about my future!"
"Tell me that you love me a lot!"
"Tell me that you hope my plane doesn't crash, but say it in a funny way."
"When you say goodbye, add something about how you're hoping I win the PowerBall tonight!"
"As I turn my back and walk away, wait two seconds and then tell me I have a nice ass!"
It doesn't happen. "Wish me luck" is the only time when we demand that another person say a particular set of words as part of their farewell.
It also creates this odd stage play of sorts, because there is only one response to "Wish me luck!"
It's "Good luck."
By asking someone to wish you luck, you can be 99.9% sure of their response, thereby creating this predetermined bit of two-line dialogue. It's like a guarantee of the future. You can be certain that there will be no surprises for at least the next two or three seconds.
Person 1: Wish me luck!
Person 2: Good luck.
Is there another instance when dialogue is so predetermined? Even when you tell someone that you love them, the responses can vary slightly.
Person 1: I love you.
I love you, too.
Love you, too.
Super love you!
Don't forget to pick up milk on the way home.
"Wish me luck" is weird. I know that most of us don't think very much about it when we say it. It's simply a phrase that we use in place of the standard "Good bye" or "See you later." Most of the time, we're probably not trying to solicit wishes of good fortune from another person. We're simply trying to make an exit.
Still, it's weird, even if you're using it innocuously. It's aggressive and presumptuous and authoritarian. It forces you and your companion into a brief and boring stage play. It's meaningless chatter laced with undertones of bellicosity.
I won't be annoyed if you ask me to wish you luck, but I may say something other than "Good luck," and perhaps something equally aggressive, presumptuous, and authoritarian.
Just for kicks.