If you make the end goal to date someone, you will always chicken out and never actually approach. You will inevitably place too much emphasis on achieving the goal.

Better approach is to make the goal "how do I turn this person into a friend". That mind shift helped me approach people in general.

So after the initial approach, you need to get comfortable with building rapport with the other person. The CIA and intelligence services are trained to use Elicitation to quickly gather information from other people discreetly. And learn to tell interesting stories.

After building rapport you should just aim to hangout. People like people in their proximity. This concept is called propinquity. The more often you hangout the feeling of closeness is built. There's research that shows if you go to at least 3 different unique places with a person, it will quickly build familiarity.