How To Handle Cheap People........

Stalling and putting the friend on the spot to pay will hurt the friendship imo.  If you know the friend is cheap, continue to pay, just don't go out as often.

Lips,

I too am very generous and can NOT understand the cheapie!!! And like you said they usually have much more money than we do!
Me being the communicator that I am, I would have to ask why they never offer to pay the bill or leave a tip! I would also probably hang out with that friend less! Or when you sit down to order tell the server it will be two separate bills!
I really despise tight people!!!

Luckily I don't have this problem.  Going out to anywhere with anyone is a distant memory!  But I do know cheap people, who did as you mention, or worse.  I don't see them anymore.  They are too cheap even to come out here to visit.  Once I quit passing out the money on my end, they quit mooching.

I just pay the tab anyway.. whatever it is, whether good or bad, it always comes back at you and to each of us, i keep a smile and don't let it enter my mind.. but maybe i might go out less often, it is a shame that a friend with money doesn't pay the tab SOMETIMES.. and you can tend to beleive maybe you are being taken advantage of.. i do things because i appreciate friends...

Why not try this:

" I would love to do lunch. I paid last time so if we are taking turns, it's your turn, right? " 

I had a friend who would literally stand there when our young kids ran up to a gumball machine.  Obviously I was the one who dug in my purse for a few quarters.... always. Such a small amount but it drove me nuts.

I also had a girlfriend in my very early 20's.  She would save her paychecks for months and not cash them.  When she did, she put ALL the money in her drawer and it was a big stash for our age.  When we headed to a bar, she brought $1.  Yep... $1.  Obviously nobody wanted to see her sit there and not drink and dwidle her thumbs so everyone bought her drinks.  >:(  It only took 2 trips to the bar for me to see the pattern and then.... no more mooching off of me.

Funny......when I saw this topic, the 1st thing that came to my mind was,"Around the neck!"

LOL

Direct is best
If already out, a direct "Hey, I'll grab dinner, you leave the tip"
If palnning to go out, "tight week for me; let's split the bill" before setting the plan.
If she says no before you even go out, then you know she's only it for the free ride anyway ..and while it's fine to be generous, ya gotta take of yourself first