Riddle, well, a fallback position is made easier by saying it casually but not as if you're not asking her out. You've admitted it was a little awkwardly put in and you'll get better at that. Since you've been talking to her, maybe you know a bit about her so you coulda asked her casually, "listen, this movie's comin out and I know you wanted to see it. Would you like to see it together on friday?" Alternatively, "would you like to have a drink or coffee on friday after work". It's almost less what you say and how you say it. I prefer specificity in your offer (ie friday, monday at 5, etc), cause then they can go "oh I'm busy that day" gracefully rather than having to admit they're not interested in you. If they're enthusiastic, they may then add "i'm busy but how about monday?" or you can ask them that. Honestly, hard to put into words cause this is pretty much an implicit skill. I'm sure PUA folk are better at putting this sorta thing into words cause they're teaching it.
JimOfferman, you are correct. I know at least two guys who have such consumate social skills that they have been able to walk out of the friend zone. I'm just not good enough to do that yet.
Actually, that's an interesting ponit you've made,
LordSappington. "We" guys tend to assume that the women get it all figured out and that they just have to say yes and make us so very happy and its crushing when its a no. But they really don't. I know a number of girls who get weirded out by attention from guys. Some of them (quite pretty) don't know how to handle advances from a guy or how to flirt. And yea, while women tend to have superior social skills (ie being able to handle different social situations) she's prolly learned a bit from this, too. She's prolly not been skipping eye contact cause she doesn't like you, she prolly can't handle this situation and she feels awkward about not being able to handle it. It's not all about you,
Riddle.
Seriously though, you're handling this splendidly with great humour. Good for you, Riddle.
You know, I've been thinking about how we find customers and how we look for partners. A lot of us do "cold calling" on random people in the bar or wherever. "Warm leads" are better, obviously. A referral or reference makes it better. A trust-inducing environment like a party thrown by a shared friend is a better setting. It's amusing to me.