It's impossible to cover flirting in every possible dimension, but I thought I'd give a few pointers to those who aren't completely comfortable with it. The focus here is on flirting in real life, not online and does not include flirting with your significant other.
1. Know why you are flirting
You have a specific reason for doing this, so keep that reason in mind when you're flirting because it may affect the approach you take and how hard you flirt. If you trying to break the ice and get someone to notice you, you'll approach it differently than if you're trying to convey to a friend or acquaintance that you have romantic interest in them. Breaking the ice may not mean a gentle touch on the arm or hand and may rely more on compliments and body language than the more overt approach you may take on someone you already know.
2. Flirting isn't always necessary or even appropriate
In a business environment in particular this will often be the case, but also many social settings. If you know it isn't appropriate or too difficult to pull off correctly, just carry on an appropriate convo for the environment and get that person's number. You can always find easier opportunities for flirting when you are one-on-one with them.
3. You can sometimes flirt with just body language
You may find that you can't flirt verbally with someone (see #2), but still want to send some message that you're interested. In these cases a big smile or wave may have to do, but you shouldn't rely on that alone unless there is no opportunity to talk to them. Follow it up at some point with a convo.
4. The flirtee may be completely oblivious to your flirting
It's so easy in many cases to confuse flirting for friendliness or even someone playing a prank. You may need to crank it up a notch to achieve your objective, but keep in mind #4. Also, some people are so uncomfortable with being flirted with that you may need to use an ordinary convo or some contrived one to get and hold their attention.
When I was 18, a 42 year old co-worker hit on me, including touching me several times on my arms and back. I had never had an adult woman hit on me before and thought my co-workers were playing a joke on me, that's how oblivious I was. One later told me she had been genuinely interested.
5. The flirtee may realize exactly what you doing and deliberately pretend to be obtuse
If you aren't getting the feedback, i.e., attention and responses from the flirtee that you were expecting, it may not mean that there is something wrong with your approach or that you need to flirt more aggressively. A personal anecdote illustrates this.
I once had an interview for an internship right before a college class and didn't have time to change out of the business suit I wore, so I had to sit in a different spot for the lecture than I normally would. It happened to be next to an attractive young woman who checked me out and flirted with me when we received our exams back, congratulating me on my grade, It was blatantly obvious that she was flirting because she had never paid me the slightest attention before and it was 2/3 of the way through the semester. Because I had a girlfriend, I just smiled and thanked her rather than bantering with her as I would have done had I been interested. She got the message, didn't flirt more aggressively, and that was that.
6. If the flirtee finds you attractive, it usually makes it easier to hold their attention
Don't let this make you lazy though- you still should leave a good verbal and body language (meaning your confidence) impression and there are lots of other attractive people out there. It does help if they're obviously charmed, but don't assume everything based on your appearance or theirs- there is such a thing as someone not taking you seriously because they don't think someone as attractive as you could really be interested in them. You also shouldn't assume that the flirtee hasn't been flirted with numerous times before.
7. You don't have to be perfect, and sometimes the mere effort is what's important
Don't try to plan your flirting step by step in advance- let it flow as naturally as you can once you've decided to flirt. Don't let fears of rejection or possibly embarrassing yourself sabotage you- even clumsy attempts at flirting can be endearing if they don't involve some faux pas like inappropriate touching or saying something really inappropriate (e.g., don't tell them they're beautiful/handsome or say something of a sexual nature). You can do this- everyone has a first time or a first time in a different or challenging environment.
8. Enjoy flirting
Never put pressure on yourself to succeed in flirting- that will take the fun away.
I know it's easy to get excited about someone who seems especially attractive, approachable or friendly, but there will always be other opportunities to flirt.
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