I just finished skyping with a friend I haven't seen in a while. we talked for about an hour. It was kind of awkward because I have trouble with small talk, or managing conversational threads as Mystery describes it. I feel I have strength in talking about subjects when the subject is clear, but when it's just small talk my jaw feels heavy and i become insecure about my deep voice. It usually doesn't happen, but when I talked to her (yes her, but i'm not trying to game this one) my mind was racing to avoid awkward silences. Luckily we have a similar taste in music so I would play something while trying to think about something to talk about. We talked about our Christmases, seeing people over break, etc. The session ended by accident (because of technical difficulties) but it was probably for the best because, as she put it "things were wrapping up anyways", which they were because towards the end it was mostly music and little talking. I guess I'm just kinda disappointed because when we first met we were able to talk for hours, into the early hours of the morning, and this time only lasted until midnight. does anyone have any tips on small talk and transitioning into deeper stuff?

One thing I personally find great is to make social observations and laugh about them.
For example how everyone in an air plane stands up and are ready to run out before the plane even connects with the terminal. (any head start they get would give them about 30 seconds over someone sitting in their seat).

So just look around you and see what s going on. You might see someone trying to chat up a girl and you might even learn some tips. In my single days we would watch suitors (strangers) from across the room and debate whether the guy had a shot or not, whether they were just friends etc) You can even dub their voices...

Hope this helps.
Dave
ultimate body language

but what about in situations where you are alone with someone? like hanging out in someones dorm room or skyping like in my situation?

Read around some of the old threads on here mate.

2-useful-conversational-techniques-vt12 ... highlight=

This is a recent one started by Ryan that I liked a lot. There was also a thread I read a while back (and I'm sorry but I can neither remember who wrote it, nor can be bothered to go back and find out who it was), who advised some techniques to help you get better at this sort of stuff. One of the techniques was to just pick a random object up and start writing about it. Just write whatever comes into your head. And various things like that.

Conversations should be the easiest thing in the world - how many people do you see/hear having conversations about completely trivial and random things - but so many of us struggle to get those thoughts to pop into our head at the right times. Those two threads I'm talking about should help you start to change that, and there are plenty of others around as well!

@Dolern The best way to get better at small talk is to literally chit chat with strangers. Talk about the weather or what ever is around you or if you are waiting in line and it is taking forever make a funny comment about it to the people around you. The more you do this the better off you be at small talk.

Small talk is so underated. You can buy books about openers, and how to start a conversation, but little is written ab out small talk. Thats cause small talk comes from your personality, you cant one line a woman forever, u got to be able to talk to her.

There is a book called how to talk to woman, might be worth buying.