Asking for work can be as awkward as asking a person out. Today’s teens have eliminated this terrible ritual with text messaging to avoid having to have any guts at all. They probably have their friends do the texting for them with the person they’re asking out’s friend and somehow a 5th party gets involved. In comedy, texting is not a reliable method to getting work most of the time. There are exceptions, especially if you’re returning to a club for the tenth time and you’re now buddies with the booker/manager. A lot of times you don’t have the cell number of the bookers you’re trying to get work from. The point is, there are other ways to ask for work. And just as important, there are times and ways NOT to ask for work.
Realize that when a booker is booking a show that’s “work.” Yes, it sounds as easy as a yes or not question but you’re not the only comic they’re booking. They have a system of calendars and pairings to worry about. Therefore, do not ask about work in the context of a non-work situation. If they’re on Facebook posting about their children, they don’t want to mix that with emails about work. Do not send your avails via IM through Words With Friends. The same goes for any other time you run into them outside of a working situation (golf course, ballgame, etc.). Use those times to show them that you’re not only social for your own profit.
I got back to my extended metaphor about bookers being like the person you want to ask out (there’s a bigger explanation in Don’t Wear Shorts on Stage). You don’t want the booker to see you and instantly think, “There he is. It’ll be nine seconds before he asks for work. Time to duck out!”
It’s a tough road from beginner comic to someone who is even going to be considered for getting paid to perform (that’s written in my book, too) so you don’t want to screw it up with your awkward social skills. While every booker is different, an email or phone call while they’re at the club during the business day is the best way (a gatekeeper in the box office will prevent you from getting through if they’re going to say “no” on the phone anyway). With some bookers it takes a lot of persistence. Most of them don’t like doing the actual task of getting around to booking. You may have to email every couple of months with your avails. The nice part is, once you get work at that club, perform well, act professional, and tip like Rahn Ramey, the booker will eventually ask you when you’re available.
Don't Wear Shorts on Stage 