One thing I think a lot of people lack is basic conversation skills. So here is my contribution. To have a good conversation, you basically need three skills. The first of these will be the topic of this post - called threading. (storytelling and emotional intelligence are the other two, incidentally)
To thread, you have to be able to master three skills. Pick, comment, and add.
Imagine this simple platonic conversation with a girl friend:
YOU: I like your dress.
HER: Thanks. It's from MACY'S, my SISTER gave it to me for my BIRTHDAY.
Step one is to pick a topic off of what she says. Now, you have three topics to choose from, 1.) Macys, 2.) Sisters, 3.) Birthdays, which I've capitalized above. You should master the ability to pick up on potential topics as they come up.
Step two is to comment on one of them. I choose birthdays.
YOU: For my birthday, I got an awesome cookware set.
(note that it doesn't have to relate to her story at all. in fact, as the man, you should be driving the conversation)
Step three is to add a couple additional topics, so that she can pick and comment.
YOU: I like your DRESS.
HER: Thanks, it's from MACY'S. I got it from my SISTER for my BIRTHDAY.
YOU: For my birthday, I got an awesome COOKWARE SET. I love DIFFERENT FOODS. I want to TRAVEL the world and learn about gourmet dishes.
HER: I love cheesecake...
And round and around we go. Note that you could have gone off in to a story at any point here. What this lets you do is hold a conversation with as few questions as possible, it also allows you to control the direction of the conversation.