Back in the saddle...a dating quandry

OK, so here's my dilemma. In a nutshell I never liked the whole "asking someone on a date" process to begin with. 4 months removed from a divorce from a marriage of 7 years, creeping up on 30 and feeling the burn of trying to get back into the dating scene...which I was never fond of to begin with.

SO...I'm in the grocery store and I see this beautiful woman with a brilliant smile working the customer service desk. I think to myself that someone with a smile that warm would probably be someone worth getting to know better. Get in line and get close enough to read her name tag, Jessica. Then I have cold feet, perform some mundane aspect of business (sign up for a shopper card) and shuffle out of the store wishing I knew what to do.

So I go home and weigh my options and realize I don't like the whole scene. First off, how does one ask a complete stranger out in a situation like that and hope to be taken remotely serious? My instinct tells me that most women would be nervous at best under these circumstances and I don't know how to put her at ease long enough to even humor the notion of meeting me for dinner or something along those lines. Maybe I'm old fashioned, I come from the school of thought that you build a rapport with someone THEN ask them out, not the opposite. Is there a good, practical and sensible way to bridge that gap?

Another dilemma is the concept of asking someone out while they're working. Is this as awkward as it seems to me or am I overreacting? On one hand she's trying to work and probably doesn't need the distraction or potential awkwardness asking her out under ANY circumstance could generate. Then you have to balance the crowd factor...too many people and you risk not having the time to maneuver or the very real notion that you ARE distracting her from her work. If it's too SLOW then you have way too many people that are aware of what you're doing and that increases the awkwardness on my end geometrically. Plus you have to face the notion that if you get shot down it's probably going to make going shopping there again a bit uncomfortable.

This leads me to my third and final dilemma. If I approach someone that's a stranger, I have NOTHING to suggest my intent in her TO her except her appearance. I would think women would be very cognizant of this fact and that a man, regardless of his intent or meaning, would subsequently be viewed as shallow.

In a nutshell...how best to approach this situation and bridge the gap from stranger to meeting with this person to eliminate the "strangerness." How to do so without creating too many waves, inviting too many possible scenes of discomfort, and how to establish enough trust and rapport in minimal time under debatable circumstances so as to even the playing feel under more appropriate circumstances....

Thanks in advance for your ideas everyone...

You are right, asking her out the first time you see her at her work wouldn't be a good idea. Although, I am pretty sure you can establish a rapport with her in a short time. She works at the grocery store, so you have a pretty good excuse to go shopping there. Start with a harmless converstaion of how her day is going, if she goes to school, etc., go from there and end with a compliment about her smile. She'll remember you next time you shop there. Be confident, relaxed and polite. Dón't forget to smile. Next, try to find a moment when there are no other customers around, and ask her out. I don't see a problem of asking somebody at work, as long as they are not put in a position when there are other people around. It might happen that she sais no (has a boyfriend, or other reasons). Just remain cool and polite, and act natural when you see her next time ( no reason to stop shopping for groceries :-) ).
Another tip coming from a woman - we like compliments. Just do not compliment on any of the body parts when first dating, it's the biggest turn off. Smile is the best to compliment on. Ask questions about her, be interested in who she is. The more she tells you about herself the better you'll know how to act when with her.

Hope this helps,
Good luck.