Above all, just start talking. The other person has just as many
insecurities as you do. They’ll be grateful you took the plunge
and started talking to them first so they didn’t have to go
through the agony of taking the initiative themselves.
Step #2: Find Your Diving Board
The easiest way to feel confident asking someone out is to
come in prepared. I call this finding your diving board. Before
you approach someone, you should know what commonality
you both share. In other words, is there a topic, place, hobby,
activity that you can use as a diving board into a date?
The formula you can use to ask someone out is:
Claim: This is where you bring up a topic or hook that you
think you might share.
Excitement: Next, you want to add the emotion. Is this going
to be fun, exciting, adventurous, silly, good…? Make a promise.
Ask: This is a very simple, direct ask for company. It can be
as easy as, “Wanna join?,” “Are you free?” or “Feel like
coming?”