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Red and Healy first met when he introduced her to the Kitchens at Litchfield when she arrived in prison ("Moscow Mule"). Since then, Red has helped Healy with communicating with his Ukrainian mail-order bride, Katya, in return for special favours from him. The pair have developed a close relationship over the many years they have been at Litchfeild.
In the first two seasons of Orange Is the New Black, Red and Healy's relationship was established. Red described it to Healy as "You scratch my back and I tell you when to trim your nose hair". Caputo also recognises that Red has Healy wrapped around her little finger, saying "Healy is so far up you ass, he can practically chew your food".
In Season Three, their relationship blossomed, with Red revealing that she believed Healy to be a handsome and good man, who at least was trying to make his relationship with Katya work. After Red's outburst, Healy gave Red some rose seeds to make her feel better after Nicky was sent to Max and after the breakdown of her marriage to Dmitri. Red saw an opportunity to manipulate Healy into letting her back into the kitchen by using her wiley feminine ways. This started out as manipulation but through the course of the series, their bond grew stronger leading them to exchange some meaningful looks at Morello's wedding. Afterwards, when Healy suggested that she wouldn't be in prison forever, that she had a future to think about, Red told Healy that "their ships passed too late in the night for one of them to change course".
Their relationship has been described by Kate Mulgrew as being "a deep friendship" and "edgy". Undoubtedly, the pair have chemistry, and no-one found Healy's brief flirtation with Judy King more irksome than Red. Red and Healy differ from other pairings in the prison in that they have not acted on their feelings. They are wise to their situation (or at least Red is). As Red pointed out to Healy, "there is no such thing as a consensual relationship between an inmate and a guard".
Their friendship/romance has ended, due to Healy resigning from his position after his mental breakdown from having to turn in his closest inmate friend Lolly for the murder of Aydin Bayat, and because of Red's transfer to Max.