It's difficult to be prescriptive with these kinds of questions, because seduction is largely an art of improvisation. There are so many factors that go into making reasonably smooth transitions from one moment to the next. What could work well at one instance of an interaction, might not go over so well in another. And that could simply be a matter of a few progressive beats difference. Plus there are factors about your surroundings at the moment, the womans personal disposition, as well as factors in her life you have no clue about.
This is why, first and foremost your fundamentals are what will ground you in the interaction. Ultimately it is what is being conveyed on a subtextual level, as opposed to what is being said.
But let's not get it twisted, the way you use your words matters, so it is definitely crucial you have a number of techniques at your disposal.
Another note, before I jump into some technical things. Seduction is not about doing everything "right," it is about making reasonable moves, and adjusting. If something is going well (as in you are getting results) you follow it, and if you throw something out there that doesn't quite land, you simply adjust (so long as you don't bomb)
With all that in mind, consider incorporating some of these conversation techniques into your approaches.
Pace your self
You don't want to be running your mouth too fast, slow down, give her time to digest what you are putting out there. There can be a tendency to feel like you have to keep talking to keep her on the line. While this is somewhat true, there is more wiggle room than you think. Of course you don't want to just be standing there blank faced with nothing to say. But you also don't want be throwing things at her a mile a minute. It is okay to jump from one subject to the next, but give it a little breathing room before you move on from one subject to the other.
Conservations are like Lawnmowers. Sometimes you pull the chord once and it goes. Other times you have to pull it a few extra times before the engine gets revving. You might not hit on something right away, so if one thing isn't quite clicking move to the next. That said, you have to give each thread it's proper shot so that it doesn't feel like you are just desperately grasping at things hoping she will hook. She will sense that you have some sort of agenda and stranger danger will kick in.
@Chase example above is great at demonstrating how to follow the thread through, even when she isn't initially being all that responsive, and generating some momentum.
That said, sometimes she just isn't biting, or whatever circumstantial topics are available don't offer material to riff on, so you have to be prepared to switch gears.
Use leading statements, more so than ask questions.
For example, say she is picking out a dress. instead of asking "So what is the occasion?" you say something like "I'd wager are going somewhere very formal (adventurous, fun, chill) with a dress like that."
Notice how the former is very pointed, and somewhat intrusive, and the latter is very open ended while also leading the conversation in a direction you are setting.
Another example. Instead of "where did you buy that jacket?" you could say "I bet there is a good story behind that jacket"
These are just basic examples, but when you are standing there in front of her think to yourself "
Leading statement's over questions"
Open ended questions
Well of course it is okay to ask questions. They certainly have there place in conversation. Something I aim to do though, is to ask open ended questions instead of very pointed ones (pointed questions can be great for teasing though). Open ended questions give the conversation an expansive path forward. Where as pointed questions pigeon hole the conversation into a very specific corner that can often be tricky to pivot out of.
Pointed question
You: Where did you get that jacket? (only one possible answer)
Her: At a thrift store
Open ended question
You: This is a unique jacket. What attracted you to it when you first saw it? (so many possible answers, she now has the opportunity to reflect on herself, and share a bit of herself with you)
Her: Definitely the colors, they are just so vibrant
You: Sounds like you like bold fashion
I try to avoid "why?" questions because they tend to put women in a position where they have to think too hard for an answer, that they might not even have. "Why?" It's almost too open ended
Instead I aim to stick to What/How questions tend to have a bit more of a leading quality
"What does that feel like for you..."
"What are your thoughts on..."
"What would happen if...."
"How can would it feel if you decided not to?"
"How will you know if you made the right choice?"
"How can you make the most of it?"
and so on
Sounds Like
This gets its own section because it is an extremely important tool. I first learned it from FBI hostage negotiator Chris Vos. Basically what you are doing is reading into the subtext of what she is saying and then highlighting that subtext for her. It is great at demonstrating that you are truly listening to what she is saying.
Her: yeah, there are too many choices
You: Sounds like you can't make up your mind
Her: ugh, yeah
You: What if I offered some perspective. I happen to be an expert in breakfast cereal
"sounds like you really value your free time"
"sounds like you put a lot of work into that"
"sounds like you want to be spanked" (just kidding guys, don't. Unless of course...).
Active listening
@Chase has this great article about this where he breaks it down. Just read it. I have been using it more often these days and it has been doing wonders for me.
The only thing I will ad here is that, while the article outlines the technique in a bit of a more deep dive sort of scenario, it works well in more casual conversation as well. Like approaching a woman at a store.
Relating
Share with her how what she is saying to you relates to you personally. This allows her to get a sense of who you are, and also takes the spotlight off of her for a moment.
Recently I was gabbing with a gal at the record store and she had selected a certain album I am fond of so I related "Yes, this album! you know how some albums just immediately transport you back to a time in life? I was going through so many changes when I first heard this and it just spoke to me. That was this really adventurous time in my life. The perfect soundtrack. When did you first discover it?"
Notice how didn't dump too much personal stuff on her, but I allowed her to take a little peek at something genuine about me.
Changing Gears/ Going more Direct
Sometimes when you approach and you are not quite hooking, or you don't have a lot of circumstantial material to work with, you will get the sense that the girl is going "okay, why is this guy talking to me?" more direct/ stating why you are there can really help.
Some lines I will often use are
"You seem chill, I wanted to meet you really quickly, what's your name?"
"You seem chill, what if we took a moment to meet each other really quickly?"
"You seem creative, I like that. Are you single?"
"I have to be honest I thought you were a former lover for a moment, you have a very different vibe now that we are talking though"
Or I will direct compliment her. So after the whole "you seem like you are putting a lot of thought to this" routine I will act like I am suddenly surprised by some quality she has or some fashion choice she has made
"Hey, that's a strong necklace. I bet you feel good wearing that"
"Wow, you have intense eyes, I wasn't expecting that. What's your name?"
Asking for compliance
Often times after using this opener you will be able to pretty much ask for compliance within the context of the opener. So if she is "putting a lot of thought" to choosing a book, and she has a number of books in her hands you can tell her to "let me see what you got" (while pointing out the books).
This works well with clothing as well, after times you can have her "hey that one looks cool let me see" (pointing at the shirt she is holding)
and so on
Putting it together
The bottom line is that there is no one size fits all routine. you have to mix and match and just throw things out and see what sticks.
Stay anchored in your fundamentals, and pace yourself. Have a number of conversational principles and techniques locked and loaded
Avoid being the ho hum, typical interview style questions guy. Or the rapid fire sales pitch guy.
Stay present with the moment, demonstrate that you are listening to her, give her the opportunity to share a bit of who she is, as well as the opportunity to see a bit about who you are.
