I'm going to hit on a few particular points, here.
Here's questions: Outside of making grandiose assumptions, what can I infer he understands about ENFP and the experience that I'm having with him? How/What would he have studied/noted if that's the type he's most interested in dating?
Rumors and anecdotes. ENFPs are amazing when combined with INTJs and vice versa. The attraction is that each type superficially meets each other's ideals. ENFPs are that sparkling energy INTJs need as inspiration and they easily tolerate most INTJ quirks, and INTJs are a solid rock that ENFPs can rely on, and INTJs reciprocally tolerate most all of the ENFP's quirks.
The problem is that the superficial attraction often doesn't develop into an attraction for the deeper levels of each other. The superficial level is so easy, it's very tempting to stay there.
There is only one cure: 100% honesty. That's more difficult than you might realize, as neither of you is very good at being honest with yourselves. That's not an insult, it's called "being human"! Honesty with oneself is one of the most difficult lessons to learn, and billions of people never learn it. So what happens is that we lie to ourselves, and then we tell that lie (that we believe) to the one we love, and they're like "Bullshit. You're hiding something," because when we're that close to someone, they see parts of us we don't see. But we don't THINK we're lying, and so instead of resolving the issue, it goes around in circles until it destroys the relationship.
So far, most of the advice I get is about (seemingly) how to cater to the INTJ so that he feels comfortable, loved, cared for, space, quality time, etc. etc.
Don't cater. Especially as a type 2, cuz that's your coping mechanism. It will work "too well", until it doesn't.
Instead, be gentle with his feelings. That's the ONLY rule, from what I've learned. Think of his heart like the groundhog, which will only come out of its burrow if there is nothing to scare/startle it. Gentle, gentle, gentle. Ask, don't judge. INTJs sorta-kinda have an "inner ISFP", which mostly describes how his feelings work. A lot of his instinctual emotions might repulse you, not seem noble enough, and so on. Your emotions are connected to your ideals: Ne with Fi. His emotions are connected with his physical presence in the world: Fi with Se.
That said, be firm with respect to reality and logistics (Te). Stand your ground for what you want, too. Don't just give in to his desires because you want to cater to him. Don't worry, INTJs really respect those that stand up to us (and are smart enough to explain how we're being stupid!). Such people are very rare ... most people aren't as smart and perceptive as an ENFP is w/r to such things.
So, be gentle, but firm. Don't hurt him, and don't let him hurt you.
Before I jump into a future with him, I do want to ensure that my needs will be important and treated as such too. At this point, I feel a genuine interest from him and I know we like each other, but I'm also
equally concerned about his capability to function in a relationship knowing he's without much experience. And sometimes,
he's just plain awkward!!!!!(I would put more exclamation points if it wouldn't be annoying to INTJ's
We'll always be awkward. We gradually become less awkward with experience. Give him the experience - heck, drag him along for experiences - and let him learn from those.
That awkwardness is also why honesty is so important. INTJs are really totally clueless about how relationships work when they're younger. It isn't that they don't want to be kind and nice and supportive, they simply don't know how. All of the INTJ's theoretical ideas don't help out one bit.
For instance, the first kiss was
amazing. The kind of feeling that I've made fun of other woman for having - you know - weak in the knees, toe curling, goose bumps, kiss

. He even said "You're an exceptionally good kisser" and he came in for 2 more kisses (each one increasing in intensity/passion) before we finally said good night.
Been there, done that. (Heck, it's the main reason I decided to read more closely and respond!) INTJs can be a lot better at that than would be obvious at first blush. Remember that "inner ISFP" with the inferior Se: you're feeling his emotion through his physical touch. You feel how much he cares in ways that cannot be expressed in words.
Notice that you thought HE was a good kisser and he said you were a good kisser. That wasn't skill. That was
connection. You both had a great deal of emotional trust for each other in that moment.
However, the past 2 attempts at kissing were practically epic fails! Like little peck kisses after he spent 15 minutes shifting his weight back and forth like at an 8th grade dance. Wha....? What happened to amazeballs kisser dude? Where'd he go? Bring him back! - WHAT IS HAPPENING HERE?
*sigh*
Been there, done that, too.
It's the lack of
connection. If one or the other of you isn't trying to connect, or is feeling awkward and/or self-conscious, the connection part doesn't happen.
Don't worry. This is normal. This is where HONESTY comes in. HONESTY builds connection. DISHONESTY destroys connection. Period. Even unintentional/unconscious dishonesty. And being honest in this manner is very difficult.
I think I'd be inclined to believe he's losing interest if he didn't, on the same date, ask me to meet his family and make multiple futuristic plans together. He also said that the conversation was so interesting he felt like we were the only 2 people in the restaurant and he lost track of time. (and proceeded awkwardly getting up because he had to get up early for work - like almost knocked his chair over)
Aren't these signs of INTJ interest? Confuscious Maximus.
In other words, he was in full-on INTJ mode. He was living in ideas, and plans, and logistics. The one thing to remember about ANY type is that while we all have our hidden side, we are not
primarily that hidden side. In the long run, we're both sides, but in the normal course of events, our primary type is where our mind usually is. Another one of the rules is that when we express either side, the other side becomes dormant. So when an INTJ is full-on INTJ, there is little or no ISFP. And vice versa, when we INTJs decide to allow ourselves to experience and process the world in ISFP terms, there is little or no INTJ present. Personally, it feels like I have to deliberately "not think" to go into that mental space. For me it happens with music, whether I'm playing piano or dancing.
Question: (knowing this will be different for each INTJ) How much awareness does an INTJ have of the other persons experience in the relationship?
Very little awareness, in general.
Well, I am. But without the impetus of higher consciousness/shock value, what awakens a person really?
You're going to start seeing a theme here: HONESTY. Self-honesty, which is in turn self-awareness.
And you only get to work on your own self awareness. You can't work on the other person's self-awareness. So, yeah, you both need to be working on that.
I have been myself, quirky, reverent of nothing, and beat the shit out of that drum. But, I've hurt many people in that wake. Isolated myself in the process. As I've gotten older, matured, and am setting an example for my children, I've found I'm not particularly happy/proud in some of my original approaches to challenging norms. It can also be said, that is the fundamental stimuli in most ENFP selfishness, which is often complained about with strict regard to relationships, some of which are with INTJ's, and hurt has followed. (Read the numerous threads to such)
Yeah. There is a good thread on this topic:
http://www.typologycentral.com/forums/the-nf-idyllic/76243-enfps-evil.html
That would be a good start to acquiring more self-honesty.
How can I hold my head up high having delved so much irrevocable destruction?
Simple. By learning from it. The mere fact that you call it "irrevocable destruction" means that you're owning it and intend to learn from it. Realize what you REALLY care about, and which of your "passions" are just gut-level instincts that you pander to but otherwise cause you no end of trouble. The problem isn't "getting what you want" but rather "getting what you THINK you want" and being entirely WRONG about what you really want, what you really care about.
That's where honesty and self-awareness come in. Again.
So the pendulum swings. And to the other extreme I went. (Yes, losing myself in the process) However, being broken and lost has been transformative. Order and balance are the laws of the universe, so it swings back, only now...I'm empowered to influence how far and with what intensity. I now know of my own strengths, and my own weaknesses. Neither to be taken lightly. The true goddess I am capable of is turning my cheek to the sun and, like a prism, refracting an incredibly full spectrum nurturing a colorful life. I only hope that can exude into the life of others as a true Inspiration...just like an evolved ENFP should; as the embodiment of the ENFP stereotype represents!
You can only be as good as you desire to be by being aware of how you hurt other people. That doesn't mean you should "never" hurt other people. Hurting people is unavoidable. But you can eliminate most of the gross cases of hurting other people, and only hurt them when you're essentially forced to by circumstance (e.g., when you stand up for yourself, but another's desires depend on your not standing up for yourself).
Don't think that you are "evolved".
You are "evolving".
There is a huge difference.
With luck, you can bring that same self-honest attitude you are trying to develop into your INTJ's life. If you both develop that level of honesty with yourselves and each other, your connection with each other will become extremely strong.