Hey Mark,

I've been doing pick up for about 2 years now and after over 1000 approaches I still can't regularly get attraction from girls I'm interested in. My issue before when I started out was that I would run out of things to talk about. Now I can keep talking but I feel like I ramble a lot and don't really get girls engaged into conversation. I can talk about things I think are interesting or bring up stories I think are funny, but for whatever reason I can't deliver what I have to say in an attractive way. Some skills I think I lack are being funny and interesting. I tried using some interesting/funny routines but they haven't helped me much.

Is there anything I could do on a regular basis to improve my sense of humor and help me become a more interesting conversationalist?

Appreciate the help

This is a massive subject. So I'm only going to give you some general direction for now.

Focus on her. Find out what SHE finds interesting. Figure out what SHE finds funny. That's the next step. Check out Dale Carnegie's book "How to Win Friends and Influence People" and practice the stuff in there.

Once you've got that down, try adding some teasing and humor then.

In terms of content, people love talking about themselves. The tricky part is that people don't like being asked to talk about themselves, because it puts them in a position where they are being interrogated. Probe around and get some basic information, people usually say more than they need to.

If they say something that you can relate to, you can weave a very long conversation from that just because of shared experience. If they say something that you're not knowledgeable about, but actually find interesting/cool, explore that.

In terms of humor/attractive speech, you can train yourself through exposure. I accelerated this by watching a ton of comedy (Netflix has ~100 hours of comedy central for streaming). You learn many lines, but more importantly you also learn a lot about humor itself.