Need some advice with this girl. How to not run out of things to say?

Well I do talk or try to talk to people normally, but I am tend to keep things short and sweet. Certain jokes I will make, but it take me time to warm up with people. When it comes to flirting I really am horrible, because some of the stuff I see or hear a guy say seems to be kind of outlandish. Sometimes when I do start joking I have been told I do get kind of mean. Then also I tend to be the type of person that doesn't really think in a "gray" type of thing. In addition, when it comes to picking up little hints I suck. Like one time I was having a conversation with a girl, and my friend was standing there looking at me like I was crazy, because I didn't pick up on what this girl said. Well there is this girl that I like, that I am nervous to ask out due to feeling like there is a high chance of rejection. She won't really go out of her way to talk to me, but will talk to other guys, and they seem to have a good conversation. Whereas myself when I do talk to her and try to ask questions she keeps it short. So I am wondering what the hell am I doing wrong, why I can't get this girl to talk whereas other guys are easily getting her talk and laugh and make jokes (that I find completely out of hand, but she responds to it). It is something that has happened quite a bit in my life to know that it is a "me" problem. On top of everything another thing is that I am scared of the whole interracial thing (which could possibly be why she wouldn't even consider me she is white and I am black). Yet the whole thing about "the heart wants what it wants." I have a hard time trying to figure out what to say and how to flirt without being creepy, or putting off that feeling of me trying to hard (even though I am, I am always trying to think about what she says if I am not to busy in my own head and actually listening.). You would think at my age things would have gotten easier, especially since I have had a few dates in my life (which I have no idea how I got them).

Updates:
A lot of people tell me if it is meant to happen it will, and that be myself. Yet none of that has happened yet and I am 31 years old. I am not trying to be single for the rest of my life.

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What Girls Said 1

  • you like keeping it short but when she does, it's a problem. what?

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    • I'm normally not a talkative person well until I get super comfortable with you, even then it's not much more. While I have noticed with other guys she is a lot more talkative. While with me there's not much going on.

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