Well, mine (which seems to have slipped through the cracks on Idle Thoughts list.) was Ask the Former Nuc Cruiser Sailor.
Ask the cop (but I know it’s been done before).
Ask the UFO investigator (I may actually do this one, someday).
If I had the time, I’d actually do these:
Ask the video game programmer.
Ask the cartoon animator.
Ask the guy with Asperger’s syndrome (someone else already did this one, actually.)
Ask the Union Organizer
Mine would probably be:
“Ask the recovering Alcoholic” (Though I did see that a drug addict thread has been done)
“Ask the guitarist”
Slee
If I were to start an “Ask the” thread, which I wouldn’t, it would have to be “Ask the make-up artist”.
I won’t start it because I’d really be bad at answering make-up questions for people if I can’t see their faces. Plus, a lot of questions would probably be, “What colours would look good on me?” And I think pretty much any colour can look good on anyone if the right shade and application technique is selected.
Hey rin - is that the shortest, most self-contained “ask the…” thread ever or what?! Great job!
slee - I go through the whole “ask the guitarist” thing, too, but I inflict guitar-talk on too many threads, so try to reign it in. Not to mention that there are quite a few of us, so its not like my perspective is all that unique…
I would post “Ask the Women who fled Corporate America to start her own Dog-Walking and Pet-Sitting Company”. And yes, it was worth it 
Ask the 20 year old chick who’s had 4 knee surgeries?
Ask the self injurer? (some day it’ll be “former self injurer”… someday)
Ask the self-proclaimed organizing expert?
Whereabouts, and with what group(s) (if any)?
Ask the squatter.
Ask the professional cartoonist.
(The two are related.)
Ask the guy who doesn’t want to talk about it.
Already done it: Ask the Horsewoman. It was fun till a jerk named nonpolar derailed it.
Ask the atheist Mennonite.
Back in my day (and probably these days too) some sorority houses had a male resident who took care of tasks that the girls preferred not to do themselves. This position was called the “houseboy.” There were several “staff” positions: the house mother who handled administrative tasks and lived in, the cook who did not live in, the “hashers” who served meals, did the dishes and did not live in, and the houseboy.
I had a very nice room with private bathroom, the house mother had an apartment suite.
Ask the guy who does UI design.
I don’t actually know how many other folks on the board work in that space; I know there’s a lot of web designers, though.
And technically I’m not really a UI designer; I do a combination of usability and interaction design, but often end up telling designers where they can stick their controls. 
I can also do UI text and technical writing if I really have to.
Ah, poop, I misremembered which thread it was that nonpolar bollixed up.
Anyway, rereading that thread, it was fun! Anyone got more questions?
The Good:
Ask the other test grader.
Ask the published writer.
Ask the woman who’s been happily married for eleven years.
The bad:
Ask the woman facing secondary infertility.
Ask woman taking high blood pressure meds.
Ask the socially awkward person.
I also meant to add:
Ask the woman who shops at Trader Joe’s (Yeah! )
Ask the figure skating fanatic.
Ask the moderately Repulican, Catholic, homeschooling mom of an only child.
Go on, ask!