Being Respectful When Reaching Out Via Email

I get it. We harp a lot on being proactive, being a go-getter, sending that email, asking that favor. However, there is an etiquette when it comes to sending emails, especially when you are asking this person for a favor or for advice. 
Case in point: I just got this email from a former student. After a brief hello, this student launched into three pages of questions. For the privacy of this student, I have blurred out their text. 

There are 32 questions in this email. I counted. And they aren't simple questions with one word answers. They are complex answers that would require a lot of time and effort in answering. As much as I adore this student (and I do!) there clearly is a disconnect between what they intended and how they came across. 

So, how do you go about asking for a favor in an email?
1. If this person is usually paid for their advice (ie: they're an acting coach or a career coach), then pay them for their time. Even if it is one question, OFFER to pay for their time. And, don't forget your manners. 
So, something along the lines of:

"Dear Twiddlywinks, I have a quick question for you regarding an upcoming meeting I have with a potential manager. Should I take in a prepared list of my type/brand? What about my casting markets? I totally understand if this question requires a longer answer, and I'm more than happy to pay you for your time. Thank you!"

2. If this person isn't usually paid for their advice (ie: they're a producer, director, casting director, etc), then first off DON'T EMAIL THEM UNLESS YOU KNOW THEM/HAVE A DIRECT CONTACT WITH THEM/HAVE BEEN REFERRED TO THEM. Our poor poor producers, directors, casting directors in this town are already swimming in random actor emails. Don't add to that. 
But! Let's say you were given an introduction or a referral to said person. Or said person gave an invitation to email them. Or you have met said person in the past. Meaning: if you already have a relationship with this person--then go about it this way: 

Flatter them.
Give the email personality.
Offer to take them out.
Be Flexible. 
Be Accommodating. 
Have manners. (Say thank you, you heathen!)

Here is an example that actually worked for me. Out of respect for his privacy, I have replaced the name and the name of his films with Twiddlywinks. Because, why not?

---

Dear Mr. Twiddlywinks,
My name is Alexandra Wright, and I was at the Harvard ART Alumni panel in Los Angeles that you were so gracious to speak at. I recognized you immediately because I am a huge fan of Twiddywinks Movie (something I am sure you have heard many times). My very Southern belle mother Dixie Lee had never baked anything in her life until she saw that movie, so I find it necessary to thank you for introducing my mother to a beater.
Also, when I was completing my undergrad at USC I was a host for our entertainment television show, and I saw a screening of Twiddlywinks Movie and then interviewed the lovely Twiddlywinks actress in Twiddlywinks film. All of this is to say, I'm a big fan.

You mentioned at the panel to feel free to e-mail you if we were coming to LA. I will be arriving on Sunday, and I would love to take you out for coffee or a drink sometime and soak in any and all advice you might have. I realize that you are a very busy man, and I don't want to be an inconvenience, so please let me know what works for you and what part of town would be most convenient for a cup of jo. 

Thank you,
Alexandra Wright

He responded:
That is the nicest darn email I've gotten in ages. 
I would love to meet up sometime - how long will you be out here? 
I'm in prep for a film that starts in July...so things are a bit crazed but I'm sure I could slip away for coffee at some point.  Is there an afternoon that might be good for you?

Looking forward to it!

---

This was 6 years ago. I'm still friends with this man. 
Another dear industry friend of mine once said, "Ask me for a favor, and I'll do it. But you'll only get that one favor. Become my friend, and you'll get a lifetime of favors." 

So be a friend. Don't take advantage of people. Be respectful. Be a nice human being :)
And remember: Please and thank you go a long way.