First and foremost, I want to thank this community for all that I've learned the past couple of months- the amount of confidence that I've gained, and the breadth of knowledge that I've received is absolutely incredible. Thank you so, so much.

I feel that there is something wrong with me. I have a genuine interest in learning about other people, and when I encounter a new person (or even a friend) over lunch, I ask a lot of questions about the other person and begin to understand who the person is, but the conversation quickly begins to die down afterwards and begins to head into the "awkward zone" or into "interrogation mode". I want to be able to make the other person feel comfortable, and be able to make the other person feel open towards me, but I feel that it's incredibly difficult for me to do. Sometimes, after a group conversation, alone time with the other person quickly becomes awkward, and I become at a loss as to what to talk about. Also, when I tell anecdotes or personal experiences, I feel that my stories are boring and try to finish the story as soon as possible- I feel that I have a lot of confidence as an individual, but lack an ability to tell stories. What are some questions that you ask another person when you go out with them to lunch/dinner, and how would you personally remedy my inability to communicate "fun"? Thank you so much in advance for any possible advices.