Hi Seddit,

Reddit has changed my life for the better in the past year, and I don't know where I'd be had I never found it. Now, it's time to confront one of my deepest darkest issues, and I made this throwaway just for it because I'm desperate for input at this point.

The problem: I have recently realized that I've never been able to keep a girl attracted to me because I ultimately get content and talk less over time. I always believed this was because I grew up an only child with little family, and as a result of being more independent have always been more content in silence than talking continuously. Now, however, the more I think about it, the more I realize that the problem is a complete inability to engage in smalltalk.

Whatever you prefer to call it, I'm talking about the little random filler in between major topics in conversation. For instance, you talk to someone for, say, 20 minutes. Of that 20 minutes, 5 are spent talking about A, 5 minutes talking about B, and 5 minutes talking about C. In between A and B there's typically a gap for a few minutes of random filler that just keeps the conversation going until the next topic is brought up.

My mind simply cannot do this. Literally, my mind just does not process anything. Yes I would be thinking about the next topic, but until it's brought up a content silence is my norm, and no matter how hard I try nothing comes up in my mind.

So Seddit, please help me. I'm trying to determine potential causes and solutions for this problem. Essentially, how does one learn to talk more given there is nothing on my mind? In other words, I don't think it's a shyness/anxiety issue because my mind doesn't reject any ideas as bad or stupid. It's that no thoughts are coming up to begin with.

I'm at the point where this is my sole focus in life until the problem is solved. I'm 24, a virgin, and have once again seen a perfect opportunity ruined by my lack of continuity in keeping a girl entertained and watched the attraction slowly decrease right in front of my eyes

Here are the ideas I've come up with thus far:

 1. Word association (Practice this in order to program my mind to do it subconsciously)   2. Take an improv comedy class (to learn to think faster, wittier, and more randomly)   3. Immerse myself in people (Currently talking to maybe 2-3 people/day at home and not working. Do something drastic and focus on maximizing my time around other people)   4. See a shrink (Not sure if there's a deeper issue at hand, but wtf, maybe it's something with the way my mind functions)   5. Vulnerability? A friend mentioned this. This could be the issue--deep rooted defensiveness that shuts out ideas before they can even come up. How could one try to be more vulnerable in order to open up more?

I open the floor to you--please give me your best and your worst. ANY input at all would be greatly appreciated.

EDIT:

tl;dr: How does one learn to be more entertaining?