I need some advice on closing a waitress/hostess, at an upscale restaurant and happy hour spot that I frequent often. I have been able to get other waitresses out on dates before, but the problem is that it takes too long and by the time it happens I am in “friend” territory.

I frequent this one restaurant/bar because my job allows me to take people to lunch or go to happy hour. Since going there, I have had a good rapport with one of the hot waitresses.

Unlike my usual AFC self, I have tried to appear DHV. I bring different people each time, wear my suit and tie, and I especially make a point to go there when I’m taking one of my attractive colleagues to lunch. When I go for happy hour I won’t stay longer than an hour or two, and always say I have too much to do to stay around longer.

It has seemed to work to get the waitress to appear interested in me. I have kept our conversations to c&f and some sarcastic negs. I did have one AFC moment come out the other day, when I was going out to have a smoke, she mentioned to me that she only had one left that needed to last for a day. I did give her a cigarette to be nice. Damn!

Anyway, the last interaction gave me an opening I think. One day I went in she wasn’t working, so the next time I went in a made a point to tell her it was unacceptable for her to expect that I seat myself. As I was leaving that same day, she made a point to tell me the days she would be working in case I came in I think that is a good sign? Trying to remain DHV, I haven’t been in to see her yet.

Anyway, I need some advice on how to close on a waitress, without being every other guy that has hit on her.

opinion opener
then say "listen im busy and i have to go, you seem interesting and i want to get to know you better, whats your phone number?"

direct, show time constraint, etc etc

yeah, i agree, its time to go in for the kill or else u could be bk in friend zone again bro. and i dont think giving her a cig did u any harm although i hope u negged her for it! lol

tip her big, and leave your number. Ask her when shes getting off, if its a weekend thats perfect cuz you can take her drinking

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You can do nice things, as long as it's in a strong personality frame - you want to help someone out by giving them a cigarette. Later, you want to leave soon cause you got stuff to do. You see?

Last night I made the move to ask her to an event that I had tickets for this Sunday. She said she would of loved to go, but wasn't able to because she had another event that night, then thanked me for asking. It actually was a pretty easy ask and not awkward after. There was an opening in the future to try again.

I stuck around the restaurant afterward, since I was there drinking with friends for Happy Hour. During the night, I found myself chatting up some ladies, who invited me to drink with them. I joined them after my buddies left, and closed a phone number. I didn't leave with them though, since I was met with some issues with other guys moving in on them. (That's another post).

Anyway, my buddy told me that I probably blew it with the waitress now since I went from asking her out to chatting up other woman. I actually thought it would make me look DHV if the waitress can see that I have other options. Either way, I don't really give a shit since I got at least one number out of the night. Just curious to know everyone's take...

You missed a chance. You could have just asked her to smoke that cigarette with you. If she's hot, she could have asked any random dude in the bar for a cig, but she asked YOU. A cigarette is like a meal, you only eat/smoke with people you like (usually).

Next time, mate =)