How to stop getting so rigid around women I like?

[Anonymous]

I have an issue when I finally get a chance to talk to women I like one on one, I tend to get very rigid. It is almost like an interviewer/interrogator, or we have an awkward silence due to not knowing what to talk about. On a normal basis, I am pretty quiet and will joke around a little here and there. The times I do talk the other person is mentioning something, which I happen to hear and might just jump in with a question or an expression. For example, if they're talking about a particular genre of Music. I might say who is your favorite artist (or top 5). On another hand I might just say have you heard this particular song, related to that genre. If I really don't know about it, I won't say anything. Most times I am just sitting there listening.

Well to get to the point I just have an issue of creating natural conversation, because I don't know what to say. Due to a variety of issues of not having an interesting topic, to possibly talking about a topic that has been beating like a dead horse, or not having an interesting story to tell. My issue is I am boring, and a quiet person. Which I don't know how to overcome, because it is almost like it is something that is too engrained into who I am, and don't know how to conquer it. It is really inhibiting me from my love life. Yeah I am an introverted shy person, even at my age. I just don't know how to conquer this issue and be a person that a woman would like to take a chance on. Since there is one in particular I would love to win over.

Updates

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PS: Another thing I should say is I tend to be very forgetful (someone might say something, I won't remember it 10 mins later). The reason I say that is that sometimes I might ask a question when they already told me, and it is like I don't care. I just really don't remember. One example of this is there is this girl I like, where I remember her birthday, favorite color, and favorite snack. There is this piece of jewelry I forgot about who made it for her, and name of the stone.

[Wonderingguyy]

This is difficult, I used to be like this when I was in school. I think the best thing you could do, is when you’re talking to someone you’re interested in, is to be straight out and honest with how you are. Even make a joke of it, say “look I’m a pretty forgetful guy so I might forget you told me that in like 10 minutes” and have a laugh about it with them instead of panicking about it. Even when you’re talking to people, you could ask them a dumb question like “you liking this weather?” and then follow it up with “sorry I’m just bad at making conversation” and have a laugh about that too. From this, it will lighten the mood, and make the other person aware that they probably have to carry the conversation instead of expecting you to. When you have a few conversations with the same person and get to know them more, you will be more comfortable and conversation will begin to flow naturally… you won’t even have to think about it. I’m pretty awkward around people as well, but I used to be much worse, and I think these things helped me the most. And in terms of taking to women, literally just practice. Start trying to make even little conversations with any random girls, even ones you’re not interested in, so you are more experienced and calm when you do talk to girls you’re interested in. Hope this helps :)