I have the exact same problem as you Ikbenrifi. My problem is let's say I met someone new, I would probably be able to have a good to great conversation for the first time even though initially for the first couple of minutes I met them I would be a little nervous and quiet. However, every subsequent times thereafter that I met them my head would draw a blank, because I would have used all my material that I would want to talk about in the first meeting I have with that person. I have trouble maintaining a conversation from one meeting with the same person to another. Sadly this is what is going to be my downfall when I meet with this girl sometime next week. She'll probably like me on the first date, but with her nature being to only want to date someone who is outgoing and not really quiet it kind of puts me at a disadvantage. In fact while I never would advise this I almost feel I will have to lie about things just so I don't look like a fool and can actually not be boring. I'm an introvert so my strategy of dealing with this is to try and make friends online. Unfortunately I wish there was a website I could think of to do this, because let's face it for me personally I don't think I'll ever be motivated to do clubs or such to make new friends, but only through online friends.
Sad part about me is that I don't have a ton of interests and many of things I did have interest in the past I no longer have the same level of interest anymore. I just feel once I've done something numerous times in the past it's no longer fun for me so I can't ever seem to be motivated to force myself to have fun. I mean I don't hate fun, I just feel all the fun things in life existed in the 90s for me and that the glory days are over and we are in an era where I feel things as far as entertainment goes have taken a turn for the worst. However despite all this, I just feel I have to force myself out otherwise I'll never be able to practice on my social skills.