What baffles me is that I can tell he has very deep emotions. I can tell by his reactions, morals, his eyes, and energy. Yet, he still seems detached. Not necessarily like he's in a shell trying to hide, more of like he is genuinely unaware of the weight his emotions has. Also, he can tend to be somewhat obsessive in his thoughts. Paranoid as well, yet he still remains detached from these obsessions. Its an interesting paradox to figure out and explain.
I think Pluto's position is very relevant in all this, in particular its hard aspects from Moon, Mercury and Venus. Also what you write in a different post in this thread about his intolerance of deceit. Plutonian energy is concerned with who holds the power. Mercury Pluto aspects tend to signify an association of knowledge with power, and therefore deceit may be seen as threatening and manipulative. Libra rising is looking for a world in which harmony, beauty and truth, and Pluto's hard aspect to Libra's ruler, Venus, could turn this into a survival issue which arouses much passion. Moon in Cancer is very sensitive, and the sesquiquadrate to Pluto suggests emotional vulnerability and a need to protect the self from emotional hurt.
The t square dominates this chart, and although it involves neither luminary nor any angular planets, everything that goes on in his life will probably express this configuration in one way or another. Venus being the chart ruler adds to the importance of the t square.
Both the Sun and Moon are very weakly aspected to other planets in this chart, and both are in their own signs. This could account for his apparent dual nature. The Moon is likely to be the outcast in this chart, because its openness to suffering will be difficult for the air and fire placements to accept. Fire is not adverse to watery feelings in the same way that air is, but in this chart the Leo conjunction makes difficult aspects (ie to Chiron, Saturn and Pluto, as well as the quincunxes which Ilene immediately spotted) - so his fire side is probably heavily defended against vulnerability. He may incline to arrogance at times, but if so, this arises from fear rather than a deep sense of superiority.
Also perhaps significant is that the Midheaven is on the Sun/Moon midpoint, which is also squared by the Ascendant. In fact the Sun/Moon and ascendant/midheaven midpoints are both together in the 8th harmonic (ie a 45 degree sort) which means that When transiting Neptune is around 4 to 6 degrees Pisces he may experience a strong Neptunian phase which would not show up using traditional transiting aspects to natal points (apart from to some extent as transiting Neptune's sesquiquadrate aspects to the ascendant and midheaven.)
Could you say something about the differences between the person he is when he is with you, and the person he is in other situations? This would further clarify how different parts of his psyche/chart are differently motivated and defended.
It is likely that he will undergo intense experiences as transiting Saturn makes aspects to his t square, starting with the conjunction to natal Chiron. There is also one more transit of Saturn to his natal Sun, which will be close during its station in the Summer (Northern hemisphere Summer). These are important times for him. A t square involving personal planets in Leo and the three heavies (Chiron, Saturn and Pluto) needs such intensity to realise its potential. It also needs courage and will-power to contain, rather than to simply act out the tension. He will need to know that he is supported so that he feels safer to share his feelings of vulnerability. But he may also need those close to him to maintain strong boundaries so that he cannot just release this pressure on a whim and therefore avoid his healing process.
If he can successfully navigate this process, he will arrive at place where he can be more relaxed and open with others, and yet paradoxically more emotionally self-reliant. He will see things more clearly, and while he may still feel outraged at deceit, etc, he will not be so thrown off balance by it. He will understand when an 'insight' is valid, and when it is a little eruption of cynicism.
I think he needs relationships in which there is place for his strength and also a place for his vulnerability - in other words a partner who can also be strong and vulnerable, and understands that the two are not mutually exclusive.