This can be hard for some people. You have a expert talker here so your in luck LOL 
The flowing conversation looks like this.
Opening statement followed by a question
They respond
You make a statement pertaining to there response and then ask a question.
They respond and in most cases ask a question of there own.
You respond and make a statement and ask a question
and so on and so on.
Its not as hard as it sounds as I will illustrate below.
First thing you do when you enter a room, bar, club is take in who is in there. Notice things about them. This will give you a feel for who will be more open to conversation and interaction and what there likes and dislikes may be. It gives the first impression.
Then you pick your target and make initial contact, Usually by doing the observing I mentioned above you can come up with a opening. This is basically the hardest part. Sometimes in groups its easier but I personally feel approaching the lone person is easier.
Be sure to smile and make eye contact a lot as well as be a good listener. Listening and really hearing what they say is crucial.
Once you have your opening. Try to ask open ended questions that require more then a yes or no answer.
When they answer this information given will lead you into your statement. Dont ask question after questions repetitively though. Make a statement so this will give them a chance to ask you something. Then you can reply to there question and make a statement of your own followed by a question to keep things flowing.
If you find the convo is ebbing this is the time to pull out your PUA Tactics. Why wait ?.. because women are not stupid, we know the pick up tricks as well as the men do and if you lead with PUA material right out of the gate you come off as…well as a PUA. You want to use the techniques without being obvious your using them. Make them part of your personality. If you force them, you are not being real and this will stop a convo dead in its tracks. Then we go back to our friends and laugh about the stupid pick up line this guy used on us. You want to leave them thinking wow that guy was interesting or fun to talk to.
I have often been on the phone with Steve who is a experienced PUA while he is out at Buckies and I can hear him talking to others. Its natural not forced, he has made it a part of his personality and can do it without thought. According to him that wasn’t always so, it takes practice. So before you hit the bars or clubs practice on those you dont really care if they have a interest in you or not. This will make it more comfortable for when you approach that lady of interest.
If you fail with the practice people dont get upset. Look at the experience and learn from it. What could you have said different to keep things flowing. Make a mental note for the next time.
Not everyone has a good sense of humor but that can be learned as well. Making amusing statements, teasing or what the PUA’s call negging can help deepen comfort levels and help open people up more as long as your not insulting. There is a fine line between a insult and a neg.
Example…
Lets go to Dunkin Donuts for a Basic practice run shall we … 
Pay attention to the words I put in bold print
I enter the building with a confident stance. Make eye contact and smile at whoever looks up to see who came in. Some will make eye contact and smile back. Some will glance away in nervousness or disinterest. ( we will work on those people later)
Already I know who is more open to talking to me.
Now I am taking them in and noticing things about them. Not the nervous ones the eye contact people.
The guy in front of me is holding a bag of Irish Blend coffee. My opening.
Me… "Oh wow they have Irish blend, I always wanted to try that, Have you had it before ? " Make eye contact, smile smile smile Its hard to be mean or ignore smiling people.
Victim… Yes its very good,
Me… I like the French vanilla blend, so far its my favorite, I hear they have holiday Cinnamon stick blend. Wonder how that one tastes. This can be a statement or a question.
Victim, Yes they do, they have had it in the pots at work this past week. ( he mentioned work, hold onto that for later)
Me… Oh really, did you try it ?
Victim… Yes
Me… Did you like it ?
Victim … No
Alert alert the conversation is lagging.
Make a statement and ask a question that requires more verbal communication
Me… We dont have a coffee machine at my work so we have to bring it in made. What kind of work do you do ?
Victim… I manage a store
Me… Thats Great, What kind of store ? I work for the post office.
You need to offer a little info on yourself to get some in return. People reciprocate its human nature.
Victim… I manage a sporting good store in the mall across town. Do you work here in (insert town name) ?
Ect Ect …
By now you have a feel whether the person is open and interested in talking to you and if you want to continue talking to them. Sometimes you may not want to. In which you can cut it short by making a statement and not asking a question. If you like the person this is where you introduce yourself. With the people who didnt make eye contact when you came in or looked nervouse and look away quick you may need to introduce yourself a little earlier but practice on the easy ones first.
Me… "Oh By the way My name is Tisha, and you are ? " Umm lets call him Ted. Go right back into the convo and answer his question.
When you just walk up to someone and say Hi My name is Tisha and then start talking its not natural or flowing. This is done more in a business setting not a social setting. As long as you introduce yourself in the first 3 to 5 minutes of conversation its not considered rude.
He just gave me a ton more material to work with. I can talk about sports, hobbies, things he sells in the store, the mall, or move toward a more personal level and ask him what sports he participates in.
The point of the above conversation is that by listening to what they are saying and holding onto those keywords and phrases you can revert back to them and ask questions and make statements even with very little response to work with. Plus you can work what you learn from the PUA’s into it slowly to perfect your own personal technique.
One more tip… Use postive speech. Instead of saying I hate Cinnamon stick coffee say I like vanilla better then Cinnamon. Postive words and phrases make people feel more comfort and inspire them to respond with positive statements. It influences there attitude and state of mind.
Whoops one more tip 
While asking a girl what they do for fun is good dont do it to soon in the convo unless you have observed they have a real outgoing personality. You want to establish the rapport first then move it into a more personal territory. Suppose I had ask the guy above "what he did for fun right after I said “I like the French vanilla blend” it breaks the flow on conversation and sends alerts up. You move into that after the first 5 minutes of convo after you have established a rapport.
Good goddess I can go on forever with tips LOL I should write a book.
Hope this helps some I am sure the PUA’s will have more suggestions for you. But its best to start with the basics when your shy. Believe me I have taken people out and given them lessons in how to approach and create a flowing convo and its something you work toward and progress with with practice.
Tisha
But ill give you a quick rundown, i like this girl now for a while, and we’ve liked each other on and off for a while. She recently told me that she liked me, and when we tried dating before, something was seeming to hold her back, but nothing seems to be doing that this time. And i messed things up in the past with this girl twice now, i would really like to make things work. I posted this here in the women’s section because i would like a woman’s take on this. OH, and if you guys want/need to know anything more about my situation with this girl or anything, just ask, i would be glad to go into more details 
) So anyways, i told her that i like her too, and we found out that we both had liked each other for a while but where i always got so nervous around her and i didn’t think she liked me, i never tried anything, or i never tried to come on too strong, but at the same time she liked me, but shes used to guys making bold moves, and guys who are like chock full of confidence, she didn’t know how to react. It was actually really funny we had quite the good laugh about it.