OMG! lieu, for the longest time when I read your posts, I pictured a buddy from college named Lou with a similar sense of humor as yours.
Now having read this post, I’m convinced I was wrong. You’re my dad.
He’s the only other person I’ve ever heard say the “tickle your ass with a feather” bit.
What a hoot!
I know exactly what you mean, TN*hippie. I certainly did my share of freezing up like that during my single years, which lasted into my mid-30s.
The great difficulty, from my perspective, is where to start a conversation with a woman when you’ve been smitten by her looks, but have no idea what, if anything, you have in common with her.
Exactly the reverse of something like, say, an Internet message board, which I think is one reason why we’ve had so many romances start here.
One idea, FWIW: ask her if there’s any particular sort of ethnic food she fancies. If she simply answers your question, then you’ve got at least a conversational foot in the door, from which one thing can lead to another:
Her: Well, I really like Salvadoran food.
You: I didn’t know there were any Salvadoran restaurants in town.
Her: Well, there aren’t any, but one time when I was down in Atlanta, some friends and I ate at this wonderful little Salvadoran restaurant.
You: So, were you living there at the time?
Her: No, I was visiting my best friend from college…
And you’re off and running. And when there’s a lull, or one of you has to get off, you can ask her out for dinner at your favorite ethnic restaurant.
OTOH, if she asks you why you want to know, you tell her that you would like to ask her out to dinner, and you were wondering what sort of food she fancied.
It may not be the most brilliant conversational gambit in the world, but Lord knows it’s far from the worst.
And if you see her again, good luck - we’re rooting for you. 
I know what works in the movies - “They’re watching me, and I need someplace to hide. Can I take refuge in your house for a couple of days? I know some valuable secrets that will blow the lid off government corruption, and by the time I’m done, I will have saved your life (probably more than once), I will be famous and honoured, and you will be in love with me.”
Or, since she smiled back at you (a good sign) try the “You have a beautiful smile” approach that someone else suggested. If she’s reading a book, try “What’s that book you’re reading?”
Of course, what do I know, I’ve never picked up a stranger in my life.
The best thing you can do is pretend to be a character from one of your favorite books of movies. If she gets it, you come off as clever and you automatically have something to talk about. If she doesn’t, than you can console yourself that you had nothing in common so the thing was doomed anyway. Just don’t pick a character that everybody knows.
For example:
Put on your best Spanish accent (think Antonio Banderas,) and say
“Eddscooze me. Joo you happen to ave seex fingers on your hand?”
She’ll look at you curiously. If she actually checks her hands and counts her fingers you know you’re not dealing with a brain surgeon.
She’ll probably answer in the negative and be curious or intigued as to why you asked.
"I am lookeeng for a pairson weeth seex fingers one one hand. That pairson keeled my fadder when I was but a boy. When I find 'eem, I will say “Ello! My name is Indigo Montoya. You keeled my fadder. Prepare to die!”
If she’s seen the movie you’re in. If you get rejected, it wasn’t your fault that she has not cultural taste, is it?
Either way you’re safe.
(I’ve never tried this. I just thought of it now.)
[nitpick]
Scylla, I think Mandy Patinkin played that role.
[/nitpick]
I know, but I can’t do a Mandy Patinkin Spanish accent, only and a Banderas.
Antonio is sexier than Mandy, so I was thinking to go for Antonio as Indigo.
Well, hopefully not too…
I was in the same situation with a very great looking (and 5’11") lady. My solution…
Shaved legs.
Next time we met, she couldn’t take her hands off me. 'Nuff said. Pity I was skippping the country three days later. Try it (shaving, not emigrating).
Actually, Mandy Patinkin is pretty damn sexy…