How to impress someone on Facebook or in real life?

Hi, I think I'm a bit of clumsy on Facebook chat. Whenever I try to chat with someone, I sometimes feel that what I reply or say is a bit misguided and sometimes people would reply to me out of mercy. I talk to a few classmates who happen to be online. I don't do so well with face to face conversation cause I'm a bit shy since I was a kid so maybe I can start conquering my insecurity by being good and interesting whilst I'm chatting on Facebook so when these people see me or talk with me in real life next week or so, they'll think of me as slightly better than what they might picture me right now as a boring guy.

There is also someone I tried to chat with the other day. I made multiple, maybe 2 or 3 hellos to get her to reply. I started asking why she wasn't in the party last week or if she's enjoying what she's doing and I said that I wasn't enjoying my holiday cause I couldn't feel Christmas was coming. I said I was sorry if I've been bothering her because I only had 3 friends online at that moment which is true anyway. Do you think I'm really boring?? How do I make an interesting conversation with people. I need to make myself appear a bit cool to them. You see, I got to be better you know so they'll start to look at me differently.