Is it ok to ask temporary employees to contribute to parties?

Is going back the next day to ask her out OK?

• Hello readers: Last night I went out with my grandparents to a restaurant and our seating hostess was a very attractive lady about my age; 20. Out of no where I decided to be try and be more friendly then I usually am when employees ask how your day is going. When I asked how her day was going we had a nice few seconds short chit-chat about the incoming dinner rush and how I sympathize for restaurant employees because of how difficult it can be. It was a genuine comment. I don't know how restaurant employees handle it. Of course being only the hostess I expected to not see her again the rest of the night. Here is the funny thing. In all my times going to sit down restaurants, I have never seen a hostess offer service to a guest after sitting them down. They always remain at the door. About five minutes or so after we had received out drinks and already ordered, she comes by us with chips and salsa (know the restaurant now?) asking if we need more and half our chips are still waiting to be eaten. This may only my biased hypothesis, but I thought it was an excuse to visit the table again. With no courage or bravery, only sheer uncontrollable desperation that this may be my last chance, I did something I never do which was try and make conversation. After making sure she was had a minute free, I start a conversation about her hair. We were both natural red heads, but mine is noticeably starting to darken. I stated my jealously in a friendly manner that her hair still remained very bright and mine was not. We had a quick one minute conversation about it, during which she was unable to keep her salsa hand steady. She spilled a few drops and was embarrassed when I warned her about it. But ultimately it was a nice conversation. As much as I wanted to ask her out, two problems were concurring as we walked out. She was busy seating some other party, and I was with two grandparents. Not the best way to ask someone out. As we left, my grandparents did comment something along the lines that as we left and she gave her 'Have a good night' line, I was her primary focus. Having only asked out woman two other times in my life and getting denied both times, I am not exactly confident in this department. Yet I really want to see if any spark was there. But the circumstances of being at a work place and having already left makes it a difficult maneuver. My family said just pop in the next night before the rush and ask her out when she is just waiting for guests. Any suggestions on what to do, if anything, or just let it go? Thanks for reading.

• Answer:

  Give it your best shot...