I'm big on waitresses as well.
Poeticallyskuac, I have disagree with you my friend. I don't care if she's been hit on by 45 dudes that day. I'm confident in my abilities to always have an intersection to direct the conversation. If I see one avenue closing - I'll take another.
As Heywood said so eloquently

... Rule of thumb with the waitresses: Don't be an asshole.
But I like the duration daygame with waitresses.
My brother, a friend (AFC), and I meet for lunch at least once a week, usually more. You start building a routine of places. This is when Zan's approach worked incredibly well.
We'd started going to one place in particular quite often. After a bit, you start seeing the same waitresses, you open a couple in different ways, testing the waters...what have you... then started dialogue with one of the waitresses. Told her she's my 'lunchtime girlfriend'. Built that connection, started kino (I'd get up, look at my brother and hug her from the side...) and then started to engage her when she came by the table. I asked about her - and listened actively. But - I didn't ask her out then. Not the right vibe to caveman.
When something could be playfully 'disputed', I 'broke up' with her - like a drama queen. Told her she was no longer my lunch girlfriend, how distraught I was, yada yada yada... all in good fun... THEN I bounced to another nearby waitress and told her I just dumped the other one for her. From now on, she'll be your lunchtime girlfriend...and nobody exists but her ...in my lunch time world...
They really had a ball with it!
In about 4 visits running this, which was from routine lunch with my brother, NOT part of any actual game I was running, I was able to date one if the waitresses and get a number for another.
No effort other than lunch banter, kidding and a transition from fake to reality via quick isolation.
I used to game everyone. Waitresses were easy simply because they were always coming to me.
Best,
RR