Greetings all, I'm new here (and new to the game). I figured you might have some suggestions on how I should proceed with this...

So my cousin and I went to one of those all-night restaurants tonight...we hit at bar rush (2am-ish), so it was rowdy and busy and full of people that generally annoy you. There were a fair number of good looking women around, but I was quite struck by the fact that our waitress was a 6'2" (seriously) beautiful woman. When she greeted us, I talked to her like a human being. The next time she came around, I asked how tall she was and then replied with "You look even taller from down here" (I was seated). She said she wasn't sure if that was a good thing or not and I told her it was.

Many of her tables were full of drunk folk that were chatting with her, and she later commented to me how she was spending a lot of time just having to talk to people. A few minutes later, I overheard her subtlely make fun of a drunk guy at a nearby table.

"You're funny," I said as she walked by.

"What? How?" she asked, seemingly not sure of what I meant.

"How you made fun of that guy just now. That was funny."

When she brought us our bill, I asked if she's usually around on weekends and quickly followed her response by asking if it was normally this busy and rowdy. I then asked if she has email. She said she does, but doesn't use it very often. I asked for it anyways ("I could use more funny friends like you", I said) and she obliged.

When I arrived home, I ran a quick search on the email and it led me to a facebook page, which most definitely is this girl. My dilemna is this...

Do I send her an email? If so, what should I say?
Do I send her a facebook message instead, saying I found her via the email and that I figured she'd probably check facebook sooner? If so, how do I then proceed?

Any and all advice is very much appreciated by this newbie. Thanks.

Why didn't you try to #-close? You sold yourself short, especially when she said she doesn't use her email very often, she might've been hinting to go for that #.

Anyway, email her, going to her FB would make it look like you're putting too much effort into her and that you don't have a million other girls' numbers and emails burning a hole in your pocket. You're a busy guy with more important people to see.

A. I'm new and don't always think that quickly...yet. I'll get there. Also, she was in a hurry...yet she asked if I had a pen so she could write it down (what kind of waitress doesn't have a pen handy?). I think you're right - I'm a dumbass.

B. Good point on the email. So how do I approach it? A "Hey, I'm that guy, what's up?" sort of thing, or a new opener with a little reminder? I'm not exactly sure what to say. I think too much.

I would say niether, just go again to same place sometime later, then when you see her just tell her,

Hi online girl, i was so busy couldnt send you an e-mail, actually yesterday i was out ( just describe a fun thing, party, movie, whatever, but show it was really fun, to make her feel that she want to be there) and thought to call you to join, but found out that i just have ur e-mail which was not helpful.

based on what you said i believe she will offer her number to u, keep us updated

Well this is a lesson to number close in future, people find it easier to ask for facebook/email when new to the game.

Personally if you really want to contact her, email her, don't FB her, will make you look like a stalker kind of thing, as if you went searching for her. Best bet as someone suggested is to go back there, get speaking again, and number close!

I agree should have number closed

Of course I should've number closed! But I didn't. I'll get better. However, all is not lost. I sent her an email with a short explanation of who I was and why I got her email before ending it with "So what do you have going for you besides your good looks and sweet sense of humor?" It's a little sugar-coated, I know, but she responded less than an hour later by pretty much telling me what she has going for her and where she is in life. She also said that she remembers me and that I was the first person to ever ask for her email.

So:

- she flat out said she's not that interesting. That means lower self esteem. How do I massage that?
- she told me a couple things she likes and said "that's the embarrassing stuff about me". How do I use that? I know there's something there.
- I'm thinking I might (half jokingly) say I got her email to make sure she's not crazy (add in a line saying I've had a few nutcases that never stopped calling, blah blah blah, DHV) and then use that to segue into getting her number - thereby validating her as not crazy, but nothing more. Good idea?

Trying to pick up girls when they're working in restaurants or shops is rough. Unless it's someplace really quiet where they're completely bored like a jewelry store or something, most working girls have too much to do to be interested in talking to guys. Remember, they're only there because they're doing a job, not because they enjoy being a waitress or shop girl and (if they're pretty) being hit on by literally every guy who walks through the door. Girls I have known who had those kinds of jobs hated having to put up with all the interest from guys. Shop girls are easier to hit on, esp. girls working on quiet shops that cater mostly to women. Hostesses in popular restaurants are probably the hardest girls to hit on because their bitch shield is armor fucking plated.

If you found your waitress friend on FB then just continue cocky/playful via email but don't expect much. Don't neg her - negs online can easily be misconstrued as verbal attacks because there is no voice tonality that comes with your comment, particularly from people who don't know you well. Cocky play with words that doesn't neg her or possibly just hints at a neg is much better. But I agree - if she admitted up front that she doesn't use email or online stuff much, you were probably better off getting a # close (which for a waitress I will tell you right now is damn near impossible unless you're a rock star or hollywood actor)

Going back to the restaurant is probably your only sure fire way to get her number. Bring a group of guy friends and make sure they are all in on your game if you really want to get her digits. Show her you're a leader of men by telling her you got your guy friends to go to her restaurant instead of somewhere else. I guess figuring out which nights she works is the other challenge....