What are you meant to say?

[GregTurner00]

As in, I can never think of a topic. If I want to know more about the girl, it feels weird to just leap at her with "tell me what music you like!", since, inevitably, straight after answering I will have no idea what to add on to that. "Have you gone to see any bands?" might cover me for an extra response, but then we're out of options.

Meanwhile, much to my dismay, I can sit and watch a friend of mine, or a random guy, speak to the girl and the conversation just ignites.

Is this mostly down to me not being as attractive, so they give me clipped answers whereas they put in more effort to speak to the better guys? Since when speaking to men it's constant laughs, when speaking to girls while in a group of guys it's constant laughs again, but one on one with a girl, I feel like an awkward creep.

Girls, what kind of things do you like to be asked? What questions should I avoid? Is there a better way to phrase them that I am missing?

Guys, how do you navigate this? What works for you when wanting to get to know a girl you like?

[quaranta]

Your concerns are valid because the conversation you'd have is not genuine from the beginning and you have to work to not make it feel fake, while it is. You are not talking with her because you have actually something to share and to say, you are not interested in a conversation per se, but in getting chances to end up in a relationship, using the conversation as a strategy to get there.

If you don't have "fake convo" skills, you'd get easily into a conversation with a woman you have something to actually talk about with, such as interests and hobbies in common, humor in common, or situations in common that happen while hanging out in a group (or while going to a lesson, an event, an activity with other people).
There is always something to comment about the surrounding, and as far as I observed, women love to make alliance through common "enemies", which also translates into common "critiques" over something, and can't wait to agree with you if you offer some very agreeable vague things ("the mass is X", "people are X", etc). That doesn't grant romantic interest, just a friendly bond, but that may help going further onto other topics, like narrating an episode of your life that resembles what you were criticizing together, and she will probably tell hers, which you should agree to. At that point you just ask more questions about that, and let her talk a lot. Look interested, say:"Really?" and let them continue talking. Once they invested enough in a conversation is like if they "paid" on it and so they gave it value. Next time you talk with them they'll be more open to have another conversation, and things unfold.
Talking about your issues, too, may spark their interest and share similar experiences they got. They are especially very interested if you talk about dates with another weird girl, crazy stories about an ex, or other weird people bothering you (for the same reason above: alliance over critiques).

Lastly, you may just copy your friend you observe as a successful example, and hear what he says. Not to memorize the exact words, but to understand what kind of reactions he tries to get and why it makes the girl respond with a lot of words.

[Jamie05rhs]

A lot of women have tried to get me to agree to hate their enemies. But I refuse to play along with that. Because I'm a peacemaker. Also, I see that as a read flag if she's always talking about beef with other people.

[quaranta]

@Jamie05rhs I see it as a red flag too and would recommend running away, but this is very, very, very common and if the author aims to random girls without any specific selection, that should work with many...

[Jamie05rhs]

@quaranta Okay.

[Jamie05rhs]

Oops; sorry for my typo.

[SueShe]

You may want to prepare a catalogue of questions, not only related to her likes and dislikes but also to her person, what she likes to do in life, her life story, what she thinks of something or an event.

Don't ever start talking about politics, mainly in the US, if you value your life, at least not in the initial stage of conversation.

Never be pushy and be natural. Don't force yourself onto a person and try to read the body language.

If you know a person prior to you asking her, try to find out more about her and then direct your question around those topics you know interest her. The rest should flow when she realizes that you take a genuine interest in what she likes. Good luck.

[Iron_Man]

I go with the flow my words speak clearly, and they flow

[GregTurner00]

But what words do you speak sir?

[Iron_Man]

Every thing

[Guy13]

See what happens.

[Changiis07]

Just be genuinely interest in what she has to say. Ask questions like after asking what kind of music she likes, ask her what made her like that type of music, favorite song and ask if she's gone to any concerts just try not to overthink about it and just keep it flowing

[In_Trance]

Chill. Let it happen

[GregTurner00]

Often times this just leads to pure silence, which I eventually have to break with one of those dumb "do you like music" questions.