It sounds like you're trying too hard. It sounds contrived. we can tell when guys are trying to pull things out of us. I am baffled at how many times I hear and see men complaining about women not laughing at their jokes or how these guys do all the talking. Maybe if you'd stop talking and just relax, a natural conversation can flow. I get the impression you guys are following some guidebook or something. Preparing your list of preplanned questions and topics of discussion. It's so boring, stiff and really uncomfortable.

Try something a little more fun that both of you can do, rather than you deciding what to talk about by "leading". Be creative. be interesting. it could be something as simple as asking about a favorite [ insert favorite thing ] that she has and then telling her you would love to know more about [favorite] and how she got into it. Like, "When was the first time you realized you were interested in that? I'd love to hear the story."

I've also noticed A LOT of men just always want there to be talking. It's like you guys get scared if there is silence. No doubt you don't want there to be no talking. But taking breathers for moments of reflection and holding space together can be VERY telling.

When i'm hanging out and someone won't stop talking, I shut down. I feel pressured to perform and it kind of grosses me out. It's like I'm being evaluated. Eeww. There are so many ways you can get to know people without using a stiff, stuffy, formulaic process that will likely not get you a second date. At least not from me. (not that i am dating right now). Look it up on the internet. Ways to hang out with people you're getting to know. Sometimes I like to play cards like Go Fish or Crazy 8s. Those are silly games that can be great ice breakers. That's just an example... obviously you'd have to do things that you like doing.

any way. good luck.

hopefully you get the idea.