So there is this really cute waitress at a restaurant that I frequent often. Today I went in there and while she was not our waitress on the way out she told the group to have a nice day. I was in the back of the group I walked by and asked her how she was doing today(lame I know) and stopped for a second. She looked absolutely mortified and didn't respond? I walked away. I don't feel like I did anything wrong but it was extremely awkward. I'm wondering if I can say anything next time I go in to help my cause or should I just give it up?

The biggest thing people forget is how your carrying yourself and the energy your giving off. If you weren't completely confident and having a good time or acting relaxed and chill throughout your time in the restaurant, chances are she already noticed your vibe and rejected you before you even talked to her. So saying such a cliche (I have nothing interesting to say) statement will cause her to go into ewww ignore mode... he's probably going to hit on me mode...

I would go in there again with friends and some girls who already know and like you as friends and focus on having a good time while in the restaurant... and come up with something more creative to say... if you notice a change in her energy towards you at all then approach again... if not... don't bother... you will get the same results unless you approach her with better energy...

Unless you are pretty experienced with women and pick up i would not bother to even try to get waitresses, bartenders, or other hired guns. Their JOB is to give you IOIs and be charming etc. It takes a different caliber of game to get these girls, and it's a type of game, frankly, that isn't always that transferable to other women so it's pretty pointless in terms of "practice" other than if you need practice just like, talking to women without coming off as a weirdo.

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As fury said, their job is to give indicators of interest and keep you comfortable, so don't mix it up with IOI to hookup with her. This is the most important thing.

Other than that, imagine yourself in her place. She doesn't want to get caught talking too much to people that she forgets her own job. In other words, she's putting her career on risk if she talks to you for too long. This might be the case for her rejecting you. Develop your approaches and you should be fine. The question you asked had nothing wrong at all, but it doesn't catch her attention.

Good luck

If you decide to pursue it, the route I would go is next time you are there, I'd use the situation to neg her.

As in, so last time I was here I sort of hit on you and you seemed really stiff and insecure, like it doesn't happen often. I'm willing to give you practice, but only if you're committed to improving your response.

Take the awkward moment and put the onus on it not going well on her.

Thanks I'm not about to give up I know she is single which def. helps my cause. Next time she is my waitress I'm going to try to neg and be much more confident. I don't give a fuck about making an ass out of myself so long as trying to improve. Thanks again.

I took me a good minute to hone in on picking up waitress and i finally figured it out....stop trying. When someone is new to Pick up, they tend to force conversation and in most cases that is what you are doing, forcing a situation so that you and a girl you are interested in have to interact. Because this girl is your waitress, or will hopefully be, the hardest part is out of the way because she is forced to have conversation with you, and she knows that dull convo with a guy means a smaller tip. So she will try to have "nice conversation" with you. All you had to do is feed off of her and let the attraction build. I agree with the above by all means neg her, because it will spark even more convo.
If you must do anything, try to get a running gag going. Example being this...
-find something stupid to disagree upon(you must be wearing a hat for this; a fedora is perfect, and regular fitted or SnapBack will work) and say "that's it! We can't talk anymore!" And tilt the hat so that it blocks your vision from her and she can't see your face. If you have a fitted on just turn it to the desired side and tilt it down just a little bit. Be sure to keep it really loose and "tongue &cheeky". Do it randomly thoroughly the meal.
If you must use a pick up line, here is one I read a while ago that really seem to work for me:
"Do you have a sec? Look before I go any further ill tell you right now I'm not going to hit on you. I mean come on let's face it, you prolly get hit on a hundred times a day so it would just be pointless. With that being said, say I wanted to talk to you on terms that would allow me to hit on you, how would I go about doing that?"

With all of this being said, I still say stop caring about trying to get the girl Anderson it happen on its own because the hardest part is already done for you. Just go with the flow and whatever happens, happens. Act like the previous Engagement never happened if she rejects you, let it roll off your shoulder like it never affected you, cuz guess what, unless you absolutely embarrass yourself, you will probably go back Into the restaurant and see her again. Basic Pick-up 101: you spend time with the girl, you get the girl.