I had to work on it. Every day. I'm pretty shy normally. Around the end of freshman year I started to get tired of being nervous every time I met with someone. So that summer I tried to meet someone new or reconnect with someone old every day. And I did.
I talked to so many random and interesting people that summer (many of whom I still keep in touch with). I actually reached out to you, but we never found a time that worked for us :)
But yea it's a skill that you have to develop like any other. Pays dividends when done honestly and earnestly.