Hi there, I thought Id try to give my perspective. Im a beginner but Ill try to help if I can
Quesited represented by Mercury/sq Jupiter and Moon: yes, he still thinks of her. He has hard feelings toward her though. Turned houses: His sun conjunct his MC quintile Pluto in 8th house
His ego (sun) is publicly (MC) transformed (Pluto) after the death (8h) of the relationship. I think its the end of the matter for him, he may have too much pride wrapped up in the way things were or ended to allow himself to go back to it. He views the querent as the negative impetus for his necessary transformation.
I believe this chart is also showing us that quesited's lack of communication or clarity of emotions may be distressing emotionally to the querent. (Jupiter conj Moon sq Mercury conj Neptune)
I think that the quesited has feelings of love/romance they are refusing to fully acknowledge. Pisces gives excellent energy to deceive ourselves, particularly when the truth forces the individual to confront a painful reality & therefore we actually
want to deceive ourselves.
Seems like a situation where acknowledging feelings is too painful or creates a schism within oneself. He may believe that he can't still love her & love himself due to the way things transpired; perhaps he felt disrespected or degraded by her behavior toward him. Note that this isnt necessarily her fault, it could come from personal insecurities she may or may mot have been aware of.
When Venus eventually conjuncts Mercury I wonder if he will suddenly find himself missing her "out of the blue" as suddenly exalted Venus will be apparent to him. With Venus in Pisces however, he may not acknowledge he is missing her in particular- he may just decide he is lonesome and search for romantic flings to fix this. (Venus, 0°06')
Mercury sq ASC from 3rd house speaks of big time difficulty communicating with the querent; the energy to communicate is fully present but it doesnt flow or is blocked
Chiron in 3rd seems to back this entire narrative up. Deep wounding surrounding obscured/mysterious/secrets (Pisces) communications (3rd house)
Communication problems may have defined their previous relationship even, perhaps this is why they separated (not due to a lack of affection), and this may be what still keeps them apart now.
I think that if querent would want to communicate with quesited again, she would want to wait for Mercury to be able to "see" Venus. Otherwise she may get a taste of his newly-invigorated fiery and stubborn ego (his Sun conj Aries MC: Mars in Taurus)
Anyhow thats my take