Is dating a skill?

So dating. I think I missed the boat on how to act natural in such a situation. I've never gone out with someone and not ended up in a serious relationship. So this idea of navigating through personalities to find a good fit is new. At what point is it fair to say you've given it enough time to decide what a good fit is? How do I not ignore red flags? I always thought I had a good gut instinct.. But past romances have proved that wrong. 

Being wooed makes me feel awkward, like someone who can't take a compliment... And planning something to do with someone you don't know is a skill I am lacking! But I vowed to take more chances and be sure to not let life pass me by, so I'll try and learn some new skills and see what pans out.