This post applies to other forecasting techniques e.g. progressions, directions as well, I think.
I used to wonder in the past why certain astrological authors wrote that cupid’s arrow strikes for a single when there’s a trine or sextile or conjunction to the Descendant or the 7th ruler, especially when Jupiter’s transiting. I wondered why can’t a square or opposition from a transiting planet to the same natal point/planet lead to singles finding their other halves?
It just occurred to me today that squares can be seen as stumbling blocks or obstacles. Naturally, if there are obstacles, it’s harder to find a partner, not impossible but just harder. Actually, when I trained with the Faculty in London, I don’t recall that they dismiss the idea that one can’t find someone in transits involving a hard aspect.
I think it’s important to look at the natal configuration. E.g. Jupiter trines Descendant natally. When transiting Jupiter squares natal Descendant, those obstacles, perhaps by way of overinflated expectations of relationships, will still manifest but resolved easily and quickly. This brings to my mind a client who had transiting Neptune conjunct her natal MC. When this transit happened to me, it was a time of upheaval for me. For her though, I noted that Neptune sextiled her MC natally. I said during the period of the transit, it was probably a time of dream come true for her in her career. She confirmed that she got promoted during this time.
Practical Astrology 