I too am one of the ENFJ's from Amargith's man harem. :P And I have RETURNED! RAWR
As far as whether the TC (air?) should go after this relationship: I would imagine at 30 that he would have maturity enough to know whether or not he wants to pursue a relationship with you. Yes, when we're young we ENFJ's are ignorant of what we really want and we play around with poor FP's (and possibly TJ's) emotions, not knowing what the fuck we're doing. That being said, I'm 28 and I've had all sorts of epiphanies in the last few years that have really clarified who I am and what I want to myself, so I can only assume the same would be true for him.
Also, I think the idea of an ENFJ/ENFP coupling sounds like an exhilarating experience. I haven't known many ENFP women but the ones I have known in real life could turn me on just by having a conversation with me
At the very least, it'll be a fun roller coaster ride and I think you should sit him down and let him know where you stand on the issue. If nothing else, you know that he finds you physically attractive.