How can I become less shy, and talk more?

I am 40 yrs of age, single and have almost same problem as yours. Anyway, I can truly understand your situation. Like for me, when there is a conversation/discussion going on, I am just keeping my mouth shut but after that I do regret that I should have said what is my opinion or what I have been feeling at that time. I can advise while you are still young, for sure there are a lot of thoughts in your mind when there is a conversation going on. Say what's in your mind, or you can start a conversation like, have you seen the movie or the t.v. series or watch the games (depends with whom you are or occasion) or places you've been to. Read magazines, newspapers, even a headlines will help to start a conversation if you think the topic is interesting for people same age of yours. Most of all, do not be afraid to tell them if you like it or do not like it, or not have been to it vice versa then you will hear their opinions and could be more interesting. Just think that if they can do it, do not be afraid to talk - you can do it also. Goodluck and have fun...