if you only read one reply, LET IT BE THIS ONE.
Joe Fresh here, from Toronto Canada. Somebody who lurks on chowhound made me aware of this thread by calling me up and saying "you've gotta tell the original poster your secret!" So here it goes, take every character in as if it were gold.
I was in your same predicament about a year ago. I was enjoying a good time with some chums at the Jack Astors in the entertainment district and had a good rapport with the waitress. I knew I wanted to see her again, but I wasn't about to stake out the jack astors for the next month (come on guys, be proactive and efficient; study smarter not harder.) So I set it up like this, and it was a slam dunk. Firstly, my friends told me at the table it was impossible to pick-up a waitress. That added fuel to the already burning desire of going on a date with this beautiful woman. Rule number one, think positive... and use any negative comments from your friends as motivation to succeed.
This is how I performed the slam dunk: I picked up the tab using my credit card. This was important as it put me in control of the situation... I knew I had about 30 seconds to turn "nothing" into something. While the wireless handheld debit machine was "doing its thing," we had all the time in the world to chat because she was staring into the screen waiting for the "APPROVAL" message to ring through. I took charge and told her this: "hey I know this is a bit random but I have 2 tickets to the Toronto FC game on wednesday, my friend just bailed at the last second. Care to join me?" This put her in a split second decision, and after slight hesitation the answer was yes. As the machine was printing out the receipt, I had her write down her cell# on the backside of the receipt. I got home thinking I might have gotten a fake number, but when I called it the next day she was happy to hear from me. Once we confirmed the date, I had to find 2 tickets to the Toronto FC game STAT.
Turned out to be the most fun I've ever had. We went on a couple of dates, and eventually I asked her if she often went on dates with customers. Her answer was no, that usually they're all belligerent and falling over her while they attempt to ask her out. In her own words: it can be quite insulting. But she said I was different. Little does she know that I was pretty hammered myself that night, but us irish are good actors.... and I played it cool.
The fling didn't last more than a couple of dates, but it was damn well worth it. I've had friends use my technique with fairly good success, but there are some important factors to take into consideration:
1.) the event has to happen in the next couple of days, don't leave her hanging more than a week or else she'll either forget about you or reconsider the entire scenario.
2.) be RELAXED and at ease when pulling this off. I was casual, with the attitude of "i don't really care if you say yes or no."
3.) if she makes up an excuse, that the event conflicts with school or something else, at least try and get her number regardless. persistence will pay off. You don't get anything in this world by sitting on your butt.
4.) if she flat out says no, show some respect and move on. she might already be in a relationship. don't take it personal.
5.) don't be the guy at 2am who is just trying to "get lucky." Or at least make sure you're not slurring your words when you ask her out.
-figure out some event that is going on and put the waitress in a situation where she has to make a quick yes/no decision
-remain cool calm and collected
-if she makes an excuse at least try and get her number
stay fresh my fellows,