well I dont wanna lift online dating, but its sure fun while you dont have time to go play on the road (lets say you're boread at work =D)
I've been doin that for over 10 years, i got ONS, affairs and even a 2 year girlfriend out of it.
Most important as said for me is: 1st DO NOT do what all other insecure and wannabe gigolos do: ask stupid simple questions and get right cocky. Probably over 90% of men get right into sexuall topics, and even more than in streetgame girls are BORED of this.
2nd do not ask booring thins other ask. so what do you do?! simple:
3rd never hold a copy past opener ready and spread it, girls will know you do so!
write something nobody else would write! always involv something you read on her profile or saw on her pics.
samples:

here i would write like: "look yummy those cookies but I'm sure you didnt bake them on your own

"

"nice bag lain there on the stairs, my friend is lookig for something like this, shes goin crazy about it! If i could get her one she'd show me those big cute eyes and finally paying back her debts, so where did you get it from?!

"
well yes i like disqualifiers =) what im tryin to do here is
a. not mention her beauty at all -> everyone else is doin that, shes surprised
b. pay attention to the detail -> nobdy else is doin that, surprised again
c. not even asking a question. if she is interested, she will write back.
ah yeah, in online dating apperance IS a big topic (because its easy do deny somoebody, no bad feelig for a girl to do so rather than in a club where she might talk to you a little just to be nice), so you better have a good pic of yourself ready
I usually noticed if you talk a bit about normal stuff and keep the girl interestest, if she wants more, its just a matter of time till she hits a sexual topic. usually i just chat back and forth a while and relax, and then suddenly she comes up with something. if not, shes not worth and move on.
hope that helps a little
your particular situation with the girl of ex-work of course is different. I might go with a simple "are you still getting orders from that asshole boss "name" at "company"?!" well not best. what i'd have dont is on purpose leave sometign somwhere and write her like * hey , i forgot my stuffed animal in the basement floor, can you pack and seal it and hand it to me? I will talk to your boss for paycheck raise too

*