I do not think he is a player. I think he takes relationships very seriously. And he probably expects others to do the same, if they want to be involved with him.
His Moon/Pluto conjunction is being sandwiched by Pallas and the North Node. He is likely very affected emotionally by love relationships and feels things deeply.
The difficulty comes in trying express those heavy feelings. He may keep his partner guessing at times. Moon/Pluto at the very bottom of the chart likes to stay hidden, for their own comfort and security. He may push people away when he feels emotionally threatened, even if he doesn't want to push them away.
The square to Moon/Pluto from Mars/Jupiter in Cancer exaggerates and magnifies the emotional turbulence. I think he might crave drama. It might be difficult to be in an intimate relationship with him because he likes things to be chaotic and intense.
He has a very difficult Sun/Mercury square to Neptune. The midpoint of his Sun and Mercury is squaring Neptune , in the 5 or 6th.
Why is that difficult for him? Mercury in Virgo likes facts, data, certainty, and logic. It feels anxious and uncertain when the facts/circumstances are not known and settled.
That exact square to Neptune, by midpoint, creates self doubt and confusion.
With the Venus trine Neptune, that energy can create a gifted writer, artist, musician, designer, etc.
But when under emotional stress, that afflicted Neptune can create an imbalance, creating the tendency towards certain vices, like alcohol, drugs, or other addictions, or the tendency to distort reality or to deceive oneself through denial, delusion etc.
That Neptune square might create circumstances where he is suspicious, for no logical reason, and jumps to negative conclusions, partially because he might crave the drama of it all?
Neptune can transcend that negative phase and be a spiritually enlightened soul and be inspirational and if so, then it would be better than what I wrote above.^^