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Okay let me start off saying that I am, or girls say all the time that I'm attractive so I've never really had to use any game or do much to get a girl. I always made sure the girl liked me or had interest in me before i started to talked to her or try to start a relationship with her. So, my "game" or conversational skills aren't really up to par and this is one of the few reasons why I've had only 4 girlfriends in my life.
I am not really lacking confidence or have much approach anxiety, but I'm a terrible conversationist, so I rarely talked to girls in high school. Whenever i talk to girls or even guys, I noticed I agree so much that the conversation seems kinda boring or dull. I also tend to agree with the other person in most cases so there really isn't any friendly disagreement and as a result the conversation dies really quick. After the initial conversation I try to engage in more conversation by asking questions, but the other person seems bored when answering.
Are there ways to improve my conversation skills so that the other person can actually be interested in talking and so that I can sound interesting?
Im kinda in the same boat. Although im still not skilled in this area I am making progress in it. The key is to listen - i mean really listen - when they are talking they will give some opening for the conversation to continue down one path or another(*see example). It's good that you are aware that they are excited/or bored at any time... this way you know there is a problem so you can start to fix it. I practice on shop staff, people that i am introduced to and in chat rooms (just started that one but its helping)
SUPERMARKET CHECKOUT (this is not an example of a pickup just keeping a conversation going)
*
Me - hi
STAFF - hi
ME - the shop seems empty is it always this quiet?
STAFF - not usually (looks board)
ME - you look board, are you here for long?
STAFF - yeah, go home in an hour (here is the chance, to keep it going)
ME - I'll bet your looking forward to it? you got anything good planned?
STAFF - yeah.... blah, blah, blah
People like talking about themselves ask questions about them... try and be genuinly interested in the person you are speaking to. It makes a big difference and will make finding questions to ask so much easier. If your struggling at anytime try one of these I found from another post.....
What do you think of the movie/resturaunt/party?
Tell me about the best vacation you've ever taken.
What was it like in the town where you grew up?
Of all the places you've lived, which did you like best? Why?
What would you like to come back as in another life? Why?
Why were you named _____? What is the origin of your last name?
What's the best surprise you've ever gotten?
What's the neatest surprise you've ever pulled off for someone?
Tell me about some of your New Year's resolutions.
What are your favorite things to do when you're by yourself?
Tell me something most people would never guess about you.
What would you do if you won a million dollars?
It comes with practice... welll I hope it does Im definatly getting a bit better at it
Hope it helps in some small way... take it easy