This happens often after I opened. I tend to get stuck in rational conversation. You often have to at first. Say you're in a situation like I'm in, traveling and there's a cute girl at the hostel. You use obvious openers like, "what's your name? where are you from, how long you been traveling, what have you done, blah blah." But I tend to get stuck in that friendly chit chat mode and have a lot of trouble transitioning to more intimate conversation that will lead to an emotional connection that will in turn lead to a hook up.

Occasionally I'll get lucky and just things align right and I'm able to get to a more intimate connection naturally without thinking about it, but that's rare and just a chance occasion. 9 times out of 10, I get stuck in logical conversation and can't get past that.

Any advice for breaking out the sticking point, some good ways of making transitions from friendly chit chat to more of a connection?

You get stuck in logical conversation because you begin with logical conversation.

If you are at hotels enough, just ask, "where are you originally from?"

That one has potential for you to keep it logical, but don't.

Most of the time when we get stuck, it is when we don't follow up, but we begin another "logical" thread/question.

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I find it helps to get into a sexual state before opening and try to maintain it, and the words will flow much better. At least get into a relaxed state like you're chilling in your living room so you feel totally comfortable. It's not the words or conversation that's the problem, it's the underlying mindstate that you are in. Change that, and the conversation should flow better.

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Quoted from a different post of mine.

I know I've been name dropping Entropy and his ebook a lot but it really does have the answers for sticking points like this.

You're stuck in Q&A mode and she's going along with it, waiting for something to happen, but you're not sure how to transition to the fun type of conversation that creates attraction. Things like being playful, teasing, roleplaying, etc are what you need to practice until they're instinctual. I'd go into more detail but the ebook explains it way better than I ever could.

You have to learn to inject C&F naturally into your "logical conversation", and it'll turn into an intimate one. Read some C&F lines, and fake it til' you make it. You'll probably overdo on the C&F and screw up the first few times, then you will know how much to inject into a conversation for it to go the way you want.

Then it becomes natural. Watching good comedies help too. I'd say it's okay to be more F than C at first, then increase the C gradually, gauge her response, know the right dosage, and turn up on the sexual vibe. The key is not to be worried about the consequences of what you say. If you go playful and hit a wrong note, the worst thing that can happen is she'll walk away, no big deal. Then, your confidence to be playful slowly builds up. When you get into the right attitude, it's contagious. She'll enjoy your confidence, and there you go.

Practice makes perfect.

I think you answered your own question, you're getting stuck in that everyday rapport building conversation. Girls find it unattractive if you're just having that everyday monotone conversation.

"what do you do for a living"
"where do you go to school"

It's all the same crap they hear over and over again. Just put yourself in a girl's shoes, you spend 3 hours getting ready and freezing your ass outside to get into a club to get "interviewed" by some guy.

Anyway, getting off my rant, I would recommend going direct and mixing in some ****y/funny stuff. Read David D's "Double Your Dating", that will be a good place to start.

-Kevin