Conversation which I suck

There is no such thing as awkward silence, it's all in your head. To keep conversation going you have to take risks, talk about how your day went, ask the other person about their day. Make connections, ask questions and don't be afraid to be a little random. Think about how you talk to your closest friends, how you can just jump from topic to topic. Maybe if it helps pretend you are talking to a good friend of yours. best of luck

Well, what an interesting post! The only real advice that I can offer is take it in little steps, find a topic you're really, really passionate about and strike up a conversation with a similarily passionate person. Don't force the conversation and just let it flow as naturally as you can. The internet and things like here and skype are your tools, use them to find people who are passionate about the same things you are and hone your conversational skills in!

There are a bunch of books on how to talk to people, like "The fine art of small talk" that also has a chapter on the things you might be doing that kill conversations, books that go well beyond what can be said on a reply on here, Give it a try.

Well I know exactly what you are talking about and I'm sure most people have experienced at least at some point in their lives what you are going through.
My advice would be :
First thing, just get OUT OF YOUR HEAD. Don't over think what your going to say or what the other person's response is going to be like. By doing that you are restricting yourself from starting what could probably be one of the most amazing conversations you've ever had.
Second, start having opinions about everything around you. You don't have to be rigid. You can be flexible about it but what you should really do is accept yourself, respect your opinions and understand that not everyone is going to have similar opinions. At least by having an opinion on things you can easily strike a conversation with someone.
Third, the way you express yourself matters. Instead of reacting to things, start responding to them. For example, if you disagree with someone then instead of arguing with them try to understand their point of view while making them understand your perspective.
Fourth, take baby steps. Start by speaking for the trashcan. Talk about absolutely anything that you can think of and slowly build on it to see what you can talk about with the person.
The funny thing is most of the time we don't connect with people because we have something in common but it is because we actually have SOMETHING to talk about. So stop looking for common interests and just let go of yourself. Put yourself out there and get rejected. It'll be fine as long as you take it up with the right attitude. Good luck! Take care <3

I agree, go get Professor X's powers XD

Try to just be more honest you know? Not all conversations are questions and answers. Sometimes they're statements because you want to express yourself and be known.

If you ever run into that awkward silence just say, "I feel uncomfortable with awkward silences", if you do it with a smile, they might laugh :). Just be honest, say what's on your mind, because that's you. And if they're going to bond with anyone, it's going to be you for you :D

Just talk about random things, a few seconds of awkward silence is okay, but find something you have in common. For example me and this one girl didn't know each other well but we started talking about the walking dead tv show. At first it was a bit awkward because that's all talked about the first few times. But then after a while we started talking about other random things and now we can hang out and it's not awkward. So find something you have in common with the person, talk about that and sooner or later you guys will get more comfortable around eachother. You have to force yourself to do it.

I never feel like I can express myself freely because I'm afraid of being judged.