Here’s what to do on a first date. A first date can be awkward and boring or it can be the first step toward love and fulfillment. It depends on the people involved and their preparation and goals. On one of my first dates I remember throughout the date the guy kept asking, “How am I doing?” This is something you absolutely should not do. First, because it is annoying and second, because nothing shows insecurity and neediness more than asking for reassurance from someone you do not know well.