Work out what you want
Have in mind the goal of your conversation before it starts. Do you want to let him know that you’re interested in him? Do you just want to catch up and have a laugh? Identify the goal and set a strategy for how you’ll achieve it. One good way to break the ice with a guy (if you’re confident enough) is to be totally honest with him and tell him what your agenda is. For example, if you’re talking to a guy who you have a crush on and you really want to discover whether he’s single, you could say something like, “When I walked over here, I promised myself I wouldn’t leave until I found out if you had a girlfriend or not!” Or if you’re on a date with a guy you’ve just started seeing and your goal is to be less shy, say something along the lines of, “I was thinking that I’ve been pretty quiet on our other dates. Today I decided I want to let you know what I’m like.” Setting a strategy helps to keep a potentially unnerving situation in perspective.
Be your fabulous self
Be the individual you are, not a clone of him. There is nothing more annoying for a boy than when a girl goes along with everything he says. Don't be afraid to express likes and dislikes or to share opinions. For example, if a boy asks what you'd like to eat or what movie you'd like to see, do not automatically respond, "I don't mind" or "Whatever you want". Accept his questions as genuine interest in you and give him an honest response. If you really don't have any preference then it is okay to say so. Your tastes and views do not have to be the same as the guy you're talking to. You don't have to listen to the same music, or support the same football team, or agree with his political or religious beliefs. It is okay to disagree with his opinions as long as you are respectful. Standing up for what you belief in commands respect and it also gives him the chance to get to know the real you and what you are passionate about.
Take risks
No one, no matter how pretty, intelligent or funny, gets the response they want from others ALL of the time. Most of us have some experience of rejection, but that is what helps us hone our tuning skills! Take comfort from this and don't be disheartened if a boy you like doesn't reciprocate your interest. The saying "One person's trash is another person's treasure" rings true here. Another saying, "You've got to be in it to win it", is also true. You don't want to be left wondering what might have happened if you'd had the courage to go and talk to him, so take a chance and put yourself on the line!
Getting what you want
Once you've got your boy's attention there are a few tried and tested tricks for keeping it. The most important thing is to show a genuine interest in him. Smile at him, maintain eye contact, maybe touch his arm to emphasise a point. People love talking about themselves so try asking him questions. Keep it simple, like, what music do you listen to? What's it like living at your place? How do you get on with your family? What's the best holiday you've ever been on? What do you like to do on weekends? If you are feeling self-conscious, an added benefit of getting a boy to talk about himself is that it takes the spotlight off you. Once he starts confiding you'll feel more relaxed and be able to talk about yourself too.
Watch and learn
Observe others and then develop your own style. Pay attention to the girls who are more confident and flirty. Watch these girls in action and take note of exactly what they say, do, and even what mannerisms they use. Not everyone is born with conversational adeptness but anyone can develop it. Mix what works with your own style.
Positive visualisation
Before you approach a boy give yourself a pep talk. The thoughts we have influence our mood and our behaviour so concentrate on happy vibes. Dismiss any negative thoughts and substitute them with positive thoughts. If you anticipate that someone is going to laugh in your face or find what you are saying boring, you are likely to feel sad, anxious and defeated. If you remember all the compliments you have been given or a time when you had a friend in stitches laughing, you are likely to feel happy, calm and confident. Visualise success and it is more likely to occur.
http://www.articleson.com/Article/Tips-For-Teenage-Girls-On-How-To-Talk-To-Boys-With-Confidence/25160
