What could I possibly say...I am too shy!! I hate that. I get even more shy with guys...as a result I'm afraid to talk to them, and when I even talk to them I talk a little and my face turns red! Can you give me advice about that problem and how to deal with it?
You got to be a little creative. Everyone has common interests. But you don't want to say: "Oh, so you like sports, well I like to read." That's the end of your conversation. So... What kinds of music/ or particular style is he into? There's usually something there. And find a common interest before you try to flirt with him too much. Then things should flow and come together more in a way that seems natural. And like when you face gets red, that should be an indicator as to maybe having more control over your emotions. Or maybe having more patience and discipline going about how you're going to flirt with a guy.
So...(example) like I saw a girl I really liked and when I caught her looking in my direction and smiling, I said: The barber must have done a nice job w/ my haircut, but I can't really tell so I wouldn't know." She laughed, complimented me and the flirting game became give and take after that. If she didn't smile I would have never said it. It's stupid, I know. So start off simple, make eye contact and use what you observe to get him talking and the ball will start rolling, and pay attention to reactions, to see if you got their attention.
Shyness is a hard thing to deal with. I'd be a lier if I said I'm never shy. However, keep in mind that who ever you're going to talk to is a person just like you and that they aren't perfect either. Also, chances are they aren't out to judge you as harshly as you think. If you start to talk and you're turning red and you think it shows.....just be honest. Be willing to say, "Sorry, I'm a little shy." Hell, some guys will think that's cute.
For guys, we have the same problem. We see a very sexy girl and suddenly we don't know what to say or do, so most guys will understand if you tell them you tend to be a little shy. If the guy is interested in you, and judging from your picture they most likely will, they won't mind you being shy and will probably go easier on you as well.
Try and think about something that calms you. Do not get stuck up over what to say let the conversation flow. Ask questions if you are uncomfortable, the longer he talks the better your chances of calming down. Think happy thoughts. All the same its kind of cute it lets the guy know you like him. Well as long as your not stuttering words and completely freaking out.
The only thing you can do to help get over your shyness is experience. I used to be terrified of guys, but once you spend more time with them and talk to them more, it's really easy to talk to them. I think it's actually much easier to talk to them than most girls. Just practice talking to guys more. it's not that hard. Be more confident in yourself and don't worry about looking stupid. I'm sure you're a fun person to talk to. Good luck!
Confidence is I feel about practice. Just keep talking to new people and the more you talk to different people the more higher confidence. If your too shy in life people will just walk over you. Be brave good luck! As the other posters said just ask questions but not too many cause generally people love talking about themselves.