Guy meets girl, guy likes girl, girl likes guy, guy spends 25 minutes too nervous to get girl

To preface the following, shortly before I met my fiancé, he and a friend were into a VH1 reality TV show called The Pickup Artist.  The show revolved around a master "pickup artist" named Mystery teaching his no-fail techniques to guys who had trouble getting girls.  The episodes were still on my fiancé's DVR when he met me (he refuses to answer if he used the techniques from the show on me), and he put them on tape thinking I would actually love the show, despite my doubtful laughing every time he told me about it.  Turns out he was right.  I was hooked immediately on the guilty pleasure trashy show, finding it fascinating how the same guys who bombed with girls using their own lines, coming off as tools or pushy or creepy or needy, or merely too nervous and inexperienced to appear smooth, could seamlessly pull off opening sets and engaging people with Mystery's techniques.  Moreover, I realized how often I see guys attempt to use these techniques, with varying levels of success.  It was basically a rulebook that if you follow exactly will truly almost always make you successful, and every once in a while I see or experience a guy who might as well be wearing a sign that says he knows about the "pickup artist" rules.... and then there are the guys who know nothing about them and could seriously use a dose of Mystery's advice and the confidence that comes with it.  The following is a text conversation (or play-by-play) with my fiancé Jonathan that resulted from my seeing the latter type of guy at the school-cafeteria-like tables at Whole Foods when I stopped in for dinner there after rehearsal yesterday: