Being a fellow introvert such as the guy your dating, I would give him a little time, and let him get comfortable with you. One thing that helps me open up more is when a girl divulges things that are "vulnerable" to myself, for example, touchy subjects, pretty much anything they don't tell anyone on a regular basis about themselves at all.. How To Date A Shy Guy. The girl he-must-come-talk-to-me-first rule is stupid and cannot apply to every guy, especially with shy guys. Whilst some sites have no fear in making themselves look like an man while trying to impress you, shy guys tend to back away from any expression of interest lest they should god forbid turn you off. They usually.