Thank you for an interesting question. :)
Perhaps the following quote by Vaughan Simons sums it up nicely...
"Words. I love them when I can find them, but I hate them when they go
missing in action."
I've provided several pages of links for you to look over, but one of
the most important "firsts" regarding conversing is do make eye
contact and don't look down or away when conversing.
1. AskMen.com - Speaking to women
Approaching women with the right attitude.
2. AskMen.com - Date conversation
What to talk about on a date.
3. AskMen.com - Phone conversation
When your girlfriend wants to talk on the phone.
4. AskMen.com - Talk to women
How to avoid running out of things to say.
5. AskMen.com - Small talk
6. AskMen.com - Phone topics
How to keep women interested in telephone conversations.
7. AskMen.com - First date conversation
Top 10 conversation ideas for dates.
8. AskMen.com : Approaching women
How to be confident.
9. AskMen.com - Conversation starters
How to make contacts.
How to Make Small Talk
The Anatomy of Successful Small Talk: A Step-by-Step Guide on How to
be a Successful Schmoozer
?Every great romance and each big business deal begins with small
talk. The key to successful small talk is learning how to connect
with others, not just communicate with them.? Bernardo J. Carducci
How to... Make small talk
3. Sharpen your meeting-and-greeting skills. You?ll never succeed if
you?re too afraid to meet women in the first place. Call it the
?homina-homina-homina? syndrome. ?All guys are nervous near attractive
women?there?s no way to get around it,? says Ron Louis, a press agent
and the co-author of How to Succeed With Women. ?But you shouldn?t let
that stop you.?
I recommend a gradual program that builds up your confidence in
increments: Start by just saying hello to 10 attractive women per day.
Move on to brief conversations, without the expectation that you?ll
ask them out. Forget the cheesy opening lines; she knows you?re
hitting on her?don?t make it even more obvious. If the best you can do
is, ?Come here often?? you?re better off sticking with elementary
stuff like, ?Hi, how are you doing?? Ask open-ended questions to get
to know her better and involve her in the conversation. Practice all
of this for a while, and you?ll have no problem moving up to the next
level: asking her out.
Conversing for Maximum Attraction - secrets of meeting and dating women
by Allen Thompson
Men's Guide to Power Words - How to Start and Keep The Conversation Going?
Essentials of smooth conversation
You can be in full composure while talking work, but when you try to
chat, you lose it.
Relationship Counseling: I am too shy to start a conversation
If that link doesn't work please copy and paste the following url into
your address bar (cached page).
How To Start A Conversation And Make Friends by Don Gabor
(Link to Ebook by Don Gabor)
The Book of Questions by Gregory Stock
The Pocket Guide to Making Successful Small Talk : How to Talk to
Anyone Anytime Anywhere About Anything by Bernardo J Carducci,
Bernardo J PhD Carducci
Talk to Me: Conversation Tips for the Small-Talk Challenged
by Carole Honeychurch, Angela Watrous
How to Be a People Magnet: Finding Friends--and Lovers--and Keeping
Them for Life by Leil Lowndes
The Fine Art of Small Talk by Debra Fine