OP – I think the idea is very sweet … in theory. But there are sooo many ways this could backfire.
I see nothing wrong with paying for the lady’s meal – and really, if she wigs out on you about THAT, you needta run from the crazy anyway. I can see how someone would maybe feel obligated – but hell if you talk to her she’s gonna feel “obligated” to say hi back to you, unless she’s a complete bitch – that’s not gonna stop you from talking to her, though. It’s not like you’re gonna ask to pay off her car or something, it’s just a cheeseburger.
Paying for someone’s meal is something that’s rarely done and it’s a nice thing to do - so it’ll make you stand out. It’s not about whether or not she CAN pay – no more than opening a door for a woman is about whether or not the delicate little flower can open the door for herself. Hell, it’d make my day, anyway – not that it’s ever gonna happen (married).
I’m for keeping it simple. One flower - and not a rose, either – something like a daisy. Sack up, go over to her and give her the flower and say … well, whatever it is guys say. “Hi, my name is blah, I see you in here a lot and I’d like to see if you’d be interested in getting to know each other a little better, no pressure blah blah blah.”
Ask for her number after you’ve talked a while, if she’s comfortable, and make some kind of joke about how “I promise I won’t call at weird hours or drunk text you.” Don’t give her your number – why? Because to me, it’s like you’re giving her a homework assignment. You wanna get to know her, you’ve gotta show you’re willing to take the first few steps.
If you happen to comment that she’s pretty or whatnot and she balks – you dodged a bullet. I can’t imagine what kinda arrogant someone would have to be to get all huffy at being told they’re attractive. OF COURSE you wanna talk to her because she’s attractive - if you thought she was ugly we wouldn’t be having this thread. Men are visual and there’s nothing wrong with that.
Leave the waiter out of it, though.
So says the old married woman who hasn’t been hit on since dinosaurs roamed the earth.
Good luck and pleeeeeeeease tell us what happens!
Voted “don’t do that, it’s creepy” but must second this:
You have to keep going there until you see her again now, just to satisfy our curiosity 
How well do you know the waiter? Would he assist you by removing a bulb or two from the parking lot light fixtures? Would he lend you his old, beat up, white panel van? Cause there’s another approach. . .
“Good friends come and go, but the best friends help you bury the bodies.” Perhaps instead of “friends,” that old saying should have been “waiters.”
Just for the record, this wasn’t MY idea! If you consult the OP, I thought it was a little off from the get go.
And there was a little more going on than just base physical appearances. There were a number of small things that cued me in that this might be someone I could get along with.
ETA: the main reason that I asked this is that I’ve had suggestions before that I thought were creepy or inappropriate that everyone else thought was sweet. In college, I had the idea to send my girlfriend a dozen roses for Valentines Day and have them delivered in her marketing class. The idea seemed like it might have rubbed folks the wrong way, so I asked the professor. She confirmed that doing so would be, to use her words, “sweet.”
Just don’t say you’re breezy. That totally negates the breezy.
Without reading other responses, I would say it’s one thing to buy a drink for a girl sitting a few seats down at the bar, but it’s another to buy a whole meal for someone.
If you want to meet her, walk up to the table and ask if she’d like to join you. Or ask if you can offer to buy her a drink. Much better than going through a third party, and also better than just picking up her dinner tab which might seem like you are trying to establish a quid pro quo.
I completely agree. It does bear mentioning that lunch in this place costs about as much as a blended drink, though.
If you go through with it, don’t order her a salad.
Or at least make it a big salad, with a cup of soup. . .
So you know she’s cheap; now you just need to find out whether she’s easy.
I think it’s creepy and excessive to pay for a whole meal. A drink is still kinda borderline, but more acceptable.
For what it’s worth, I’ve had guys buy me drinks and usually I just go over to say thanks, make smalltalk and leave as soon as possible. I’d vote for just going up to her and saying hi.
IMHO, buying a woman something without having been asked or already being in a discussion with her puts the woman in a bit of an odd spot - she may be wondering whether or not you expect something from her in return.
Don’t buy her anything. If she’s enough of a regular that she’s familiar with the waiter then I don’t think she would be put off he told her that you are another regular customer of his (as well as a friend) and that you have noticed her in the restaurant before and it would really make your day if he could introduce you to her. It’s then her choice whether to meet with you or interact with you in any way.
Woman generally don’t mind being complimented by strangers. What makes them upset or mad is any indication that the stranger expects something in return. (When women do get upset by strangers’ compliments it’s usually because they’ve had enough bad experiences to be automatically wary.) Paying for her meal or drink will be seen as expectation of wanting more.
If you notice her again, and are sitting within casual speaking distance(maybe use your waiter friend to arrange this), and there’s a game on that she’s paying attention to, maybe say something like “Are you a football fan?” If she responds positively, maybe use that to segue into a conversation of the game you’ve been watching, or maybe “did you catch the match between X and Y this weekend?” or “What do you think of x’s chances?”
If this develops into a nice conversation over lunch about the soccer series then maybe, when the check comes, you say “My treat, I don’t often get to spend a lunchtime in such pleasant conversation with a fellow fan.” If she accepts this without withdrawing or showing signs of her creepometer ticking over, then as you’re leaving you might try “Maybe we’ll get the chance to watch a whole game together sometime. Just not V or Q, those teams are total shite and I wouldn’t want to put a lovely lady like you you through something like that.”
If you’re not actually enough of a football fan to fill in the blanks in this conversation mock-up, then you really shouldn’t try it.
Enjoy,
Steven
Rape jokes? Really?
Pretty damn well. He’s really psyched up on this. Today he brought it up again. He’s ready to give her my phone number the next time he sees her; I had to talk him down. I told him that if I see her again and am in the mood, I might talk to her. He is not at all satisfied by this course of action. He really wants to see this thing happen. I guess that beats the alternative.
But of course! You’re at the SDMB where rape jokes are always HILARIOUS!
As much as I dislike the word creepy as I mentioned upthread, your waiter friend is starting to come off that way. You’ve told him no and he is ignoring that and hitting the throttle for full speed ahead to creepland. Does he always dismiss your decisions and forge ahead with his own ideas for your life regardless of how you feel?
There are those in the world who would never get any play if it weren’t for an outgoing friend making the first move on their behalf. This doesn’t make them bad people, and some great relationships have begun this way. Sometimes social lubricant takes human form, and there’s nothing wrong with that.
Best of luck to you.
Enjoy,
Steven
He’s all right; you just have to know him. That, and he wouldn’t do any of the above without clearing it with me. He’s just cajoling at this point. It’s certainly not the first time I’ve had folks very enthusiastic about fixing me up.