@ 23 :
Ok. Here goes.
You = Mercury, in its rulership, exalted, in Jupiter's term (I guess this would mean you are interested in knowing the answer)
Him = Jupiter, in its own triplicity since this is a night chart, dignified by term.
I think it is quite apt that your significators are placed in the 3rd and 9th house respectively. My take on this is that Mercury is separating from a trine with the Moon and will soon be retrograding. Moon as co-significator will square Jupiter rx AND Saturn.
I read somewhere that the "meat and potatoes" of the chart are found in the dignity, aspects, mutual receptions etc of main significators. Based on this, I'd say that if it were a yes, it would be with difficulty.
I noticed that if you used quincunxes, you would definitely have one between main significators when Mercury retrogades back to about 5 degrees of Virgo.
However, I read that quincunxes, while generally "no", can be taken to mean "yes, if you are prepared to make some major, significant change."
P/s Still haven't worked out how to get definite answer. After reading dr. farr's answer have been playing around with whole sign charts. Still waiting for book to arrive in post.
Linear Mode
