Going over to talk to someone can be the hardest part of flirting; sometimes the words you need to break the ice just won't come out, especially if you're shy.
Don't go in there with some cheesy chat-up line or without the slightest idea of your next move. Start with a smile. This technique works; you will know immediately if the person isn't interested, as the gesture won't be returned. If you get a smile back, it can give you the confidence to go over and talk.
Play to Your Strengths
Initial contact is still only one element of flirting.
One tip for flirting with someone is to play to your strengths. This might seem like nonsense, as shyness is more often than not considered an undesirable attribute. Yet, it doesn't take much to transform shy and nervous to silent and mysterious. This technique means you don't have to force conversion that doesn't seem natural to you, giving you time to think of something witty to say when you add to the conversation. The trick with this method is in the eyes, keep eye contact and try to use your eyes to flirt. Practice this in the mirror at home.
Fake flirting doesn't mean to tell someone you are an astronaut or secret agent; it's about acting confident, even if you don't feel it.
It's an unfortunate fact for shy men, but people are attracted to confidence. Rehearse flirting situations at home, putting confidence in your voice and walk. Practice makes perfect. When you feel you ready, try out the confident-you on someone you have your eye on. As your nerves disappear, you will no longer need to put on an act. Be careful not to lose your personality while putting on an air of confidence, as it isn't a good basis for a long-lasting relationship.
Trial and Error
Write down any ideas you can think of for a flirting situation.
The may include ice-breakers, topics of conversation and compliments. When you buck up the courage to flirt, try out a couple of your ideas. If the idea produced a positive response then give it a tick. If it didn't , then put a line through it and never try it again. After a process of elimination, you'll have a list of proven flirting techniques at your disposal, which you can use whenever you need them.