I just realized he's 20. That was my favorite age because it was the most confident, if not cocky, I've ever felt. Once I hit 30, it's been nonstop stress and anxiety about the future. Life's too short to be shy in one's carefree youth when nothing else matters but the present moment.
Shy guys are the worst, IMO. Maybe that's because I'm an extrovert, but if the natural chemistry isn't there at the start, it's just a downward hill into awkwardness. Of course the sex is bad, followed by uncomfortable silence, ultimately ending in a walk home of shame.