Just talk, and learn how to begin and build a conversation.
Start with people who aren't intimidating, then move to people who are only slightly intimidating, and so on, until you are able to hold a conversation with anyone.

If you are really super extra shy, start online, then move to initiating convos with the people who do not live in your computer.

Also, remember whatever insecurity you have most others share it. And, unless you have someone specific in mind, I'd start with a bit older than 30, maybe a full on cougar 40ish woman. She'll teach you something, hahaha.

P.S. use condoms and be safe :)