Alotta times, I would be hesitant to start conversations with people out of fear that I would not be entertaining enough and I won't seem interesting. I felt like I had to come up with a good conversation topic first, and then only stick to it when we were talking.

Now I just start talking, even if it starts out as something boring. As long as I give room for the other person to person to add to the conversation (not just ramble on), and leave oppurtunities for a change of conversation, I eventully find ways to have entertaining conversations, throw some good jokes, and to connect with the other person.

That is important.

It amazes me that many people are not having fun while running a pickup.

If you arnt having fun and being happy how can you expect people to be happy about you talking to them.