Amy Winehouse and her ex-husband Blake made the headlines with their stormy, toxic relationship. We now have an A rated birth time for Amy, so I can look at the synastry again. First a quick look at the important synastry aspects effected by these transits.
His Jupiter on her Vertex is a great karmic pull and leads to excess and indulgence. His Mean Lilith falls close to her South Node in her 7th house. So he was her taboo lover or possibly even an enemy from a past life. His Chiron squared her Mars/Lilith opposition, which is domestic violence, love/hate and also the drug abuse, Chiron is poisons, Lilith forbidden fruit.
MARRIED 18th May 2007
At the time of her wedding to Blake she had the Moon on her North Node. So despite the impression we get of him being a bad influence, this marriage may well have been an attempt for her to move forward and become the strong warrior queen represented by fixed star Bellatrix on her North Node.
At the time they married, Pluto was still approaching Amy’s Moon, it would retrograde between her Moon and Neptune for most of their relationship finally crossing it at their divorce. Moon in hard aspect to Pluto is probably the most difficult transit one can have in a lifetime. Amy’s Moon is trine Blake’s Sun, so he was getting the trine from Pluto to his Sun which is much easier to handle. For her though relentless, gut wrenching transformation to the very sensitive Neptune self-sacrificing Neptune influence and this is toxic purging. She lost so much weight over this time too.
Blake became that Plutonic muse for her, those mournful, soulful love songs brought her fame and fortune. Cathartic for her and gave his Sun fame too. “Back To Black” was dedicated to him. Chiron at this time is conjunct her Ceres, again I think this is to do with her rapid weight loss. Although she was reaping the harvest of her success, she seemed to be loosing herself in the process, wasting away literally. Jupiter on her DC shows the marriage itself.
BLOODY FIGHT 23rd August 2007, 12.30 am
“Bloodied and bruised Amy Winehouse stands by husband who ‘saved her life'” . We have a time for this so that will make it more interesting. The very time dependent Tr Moon was on her Ophiuchus South Node which is conjunct her DC, (the partner). The star Sabik describes her partner on the DC “ causes wastefulness, lost energy, perverted morals, and success in evil deeds.” 
So the Moon is highlighting this “evil” tendency in her chart. Tr Neptune was opposite Mars while sitting on her Lilith too (04′). More forbidden fruit in the shape of the drugs binge. Tr Neptune opposite Mars can indicate addictive behavior, Lilith just makes it worst. Tr Chiron is right on her MC the very public wounding (09′). The Tr fateful Vertex is pinging that by a stressful square. Tr Venus on her Mars, a lovers tiff that went horribly wrong.
DIVORCE 20th August 2009
This is the big one. Tr Pluto is on her Moon by JUST ONE MINUTE! A stunning example of using precession for transits. Termination (Pluto) of a domestic situation (Moon). Tr Saturn (More endings) is on her Sun too (23′). Tr Jupiter is on her Lilith opposing Mars and on this day the Moon is on her Mars also. Jupiter here liberating her from the Plutonic prison, rescuing Persephone from the Underworld. Maybe her father had something to do with this, as her protector. But a very emotional day for her with Moon on Mars and probably a welling up of anger too. Chiron was opposed her Venus (09′) Simply the painful ending of a love affair.
This was a huge day for her, life changing, as her mystic rectangle is activated across two corners. Transiting Yods all over the shot. Mars opposed that addictive Neptune of hers, apparently cutting herself off from temptation and/or her Saviour figure. A build up of so many aspects, just shows how momentous this split was for her. One wonders what would’ve have happened in hindsight if they had worked it out and stayed together.
PLUTO THE TRANSFORMER
So why was this relationship so important for Amy? Amy and Blake have the classic; his Sun trine her Moon (36′), but no Mars/Venus aspects which I think you need to add love to smooth out the more intense sexual aspects they have: Sun opposed Pluto (52′), Sun square Lilith (96′), Mars square Chiron (30′), Chiron square Lilith (49′) All hard aspects which could turn quite S & M when aggravated by difficult transits..
His Saturn trines her AC which is probably why they married, she needed a rock. Lilith is triangular relationships and it figures quite strongly in their synastry. This could be with Blake and his in-laws as well as Amy and Blake’s ex. Lilith is strong in Amy’s chart being as it is in a mystic rectangle with the Nodes and opposite Mars. With True Lilith conjunct the MC, she is iconic of the taboo woman, the mistress and the bad girl.
Pluto came along to purify Amy’s relationships and her marriage to Blake came a cropper. But with Pluto on the Moon this was not just about her partner, it was about the relationship with herself as a woman and possibly her mother too. Alas, Amy did not really pick up after the break up. So I think it shows whoever the partner was, Amy would still turn them into monsters until her own demons inside were exorcised. Her charts is full of black holes as you can see from her natal chart.
2. Fixed Stars and Constellations in Astrology, Vivian E. Robson, 1923. p.199.