The other night I went out with some friends. Painting the town red and all that young adult, barhopping stuff. While out and about, one of my friends was deciding whether or not to text this guy and tell him to come out with us. The age old problem. 
Now this isn't the first young person who seems concerned with whether or not they should talk to the person they are attracted to. You like someone but you are worried they will think it is too desperate or they aren't attracted back or what if they do like me back?Well that justs opens another can of worms, doesn't it?
So here is my solution. Instead of getting so stuck in the what-ifs of your own mind just simplify it. Easier said than done you say? Wrong. Think of them as someone else, like a friend or a sibling. But they aren't, you may respond. So what? When in doubt about whether or not to talk to that special crush ask how you would act if this were someone else. Would you text this to that other person you thought of? If so, then just do it. Take the stress out of the decision. This can help you out until you come up with a more long term plan for whether or not you want to kick it up a notch with the flirting.