I've always had a hard time talking to people. I've always been shy and introverted. In grade school I was the kid who sat by himself at lunch because I was too shy to talk to others and didn't have much of anything to say anyway. I was the kid that watched other kids play on the play ground at recess but was too afraid to join in. Afraid to talk to people because I was afraid of not being accepted. Afraid of being rejected or something. Maybe it was the way I was raised. Both of my parents are introverts. Whatever.

Anyway I have been practice talking to people online lately. I know what some of you are going to say. It's not the same as getting out in the real world and practicing. Yeah yeah, I don't want to hear it. I just want to get to where I can hold a conversation first before going out and practicing in the real world. If I can't even do that online how am I going to do it in the real world. I would rather practice behind a computer screen, it's less humiliating. For now anyway until I build up some confidence and get comfortable at it.

Where I am at now is that I don't ever have anything to talk about with other people. I run out of things to say and then there is the awkward silence. The conversation is alway plain and ordinary and not very interesting. Then I get blown out because I have nothing to say and the conversations doesn't really go anywhere.

I tend to look for people with similiar interests so I can come up with something to say. Most people don't fall into that category and it makes it hard for me to connect with them. So then you got the "hey, how's it going or hi, what are you up to?" openers. Which don't always go anywhere.

Can anybody relate to me here. How have you gotten past this block? What do you talk about? I feel like a social retard. It's not just girls, I can't talk to anybody. I don't want to use routines that are over used and just seems like you're are trying to entertain them. I don't want to memorize a bunch of crap and then have the same conversation with each person.

I'm not conserned with picking up girls here, but just being social in general. Keeping a conversation flowing and interesting. You have to crawl before you can walk.

Any advice from someone who has gone from a social retard to a good conversationalist?

I understand where you are coming from, I grew up in similar circumstances. First off, practicing online is a fantastic idea and you should keep at it. As for keeping conversations going its smart to ask a question, give an opinion in the form of a statement, and follow up with another question.
example:
Q: Have you ever traveled out of the country?
A: No, I havent but I have always wanted to.
ST: Same here, Id like to visit Germany, France and Japan I've heard they are wonderful

at this step the person you are questioning will follow up with another comment or another question and if they dont, ask them what places they have in mind.

Also think ahead, I used to ask questions with not a clue in hell how to follow up, and deliberately bring up topics that you know you can discuss, some people can talk politics, some can talk video games, some talk school and teachers, find what you are good at and build on that in conversation. Also expand on other topics, take up a hobby or take some kind of class whether it be dance or martial arts, and it is just more wood for the fire of conversation

_________________
Pain is Temporary, Pride is Forever

You can be an interesting person in your own unique way. Your post was interesting to me not because it talks about the latest trend in shoes or the best player on a sports team, but sheerly because of its honesty.

In terms of maintaining a conversation, it can be difficult if it isn't meaninful when you are an intellectual introvert. What can you do to make even the most pointless conversations a fun and meaningful exchange of ideas?
Of course should you ever come across the most pointless conversation, it'd do you more good if you left it to talk about something else.