I did not think it took 22 steps to re-x. But okay, if it works for you do it.
It should happen right away. If you are waiting longer than 10 minutes for anything to appear on top of the second shot glass and nothing is showing up, then its because what you sucked up didn't contain any extra solvent.
As 18 hints at, you can easily just pour off the extra solvent in the second shot glass. No need to suck anything back up. If you cant pour anything off then i would say you're good to go.

"I am cursed by the blossoming knowledge of my feminine ideal and she looks suspiciously like you."
"Everybody is a genius. But if you judge a fish by its ability to climb a tree, it will live its whole life believing that it is stupid." -AE