Ruben Oliver is a charming and well educated portrait artist.
He is an educated man. His wife died. His friends write the papers.
Series 3 - 1924
At the wedding of Thomas Shelby and Grace Burgess, Ruben immediately finds himself entranced with Polly Shelby. He speaks to her a number of times, clearly attempting some romantic advances including bringing some champagne to her room but she has yet to trust him.
He attempts to introduce himself to Thomas but is ignored, mainly due to Thomas's focus on Russian business at the wedding.
Later Polly approaches Ruben to commission him to paint her portrait. He again attempts mildly flirtatious conversation but Polly is resistant and reserved. Indeed, she suspects his advances are only because he wants the thrill of dating a gangster. After telling her that his wife was deceased, that he sees her as an artistic eclectic and then openly telling her that he wishes to sleep with her, though she does not shut him out or advance it further herself she does allow his painting and their relationship, as it stands, to continue.
They came from different society, he's a well-educated artist but she was never educated. She is the matriarch of a criminal gang and a murderer. However, he's fascinated by her beauty, saying she's a woman of substance and class. He pursues and seduces her until things begin to develop between them.
Finally, Polly decides to come to him at night and sleeps with him. Polly trusts him in the end and starts sharing a secret about the murder of Chief Inspector Chester Campbell.
Next day, he leaves her because he's ready for her underworld life. When Charles Shelby's kidnapped, Thomas makes her believe that Ruben betrays her. However Ruben comes back and makes it clear that he's never betrayed her. He tells her that he's ready to enter her world. She tells him that she wants a dull life and him, then they embrace and kiss.
Later Polly is imprisoned for the murder of Campbell and nearly executed but later on released. Nearly 2 years later, Polly is alone without Ruben Oliver. She says to Ada Shelby that she's lost a man.
Polly Shelby: "You've got to tell me the reason, otherwise I'll never be able to trust you."
Mr. Oliver: "The truth is that I slept with the wife of one of the colonels who sat for me. But that was 12 years ago. And the aristocracy don't believe in forgiveness."
Polly: "Neither do the Shelbys."
"To me, politics is deliberately making things better for some people by deliberately making them worse for others."— Ruben Oliver to Ada Shelby
"It's yours. It belongs on you. A woman of substance and class. Believe me. I've painted many women who don't belong in their expensive dresses."— Ruben Oliver to Polly Gray
"I am planning to seduce you eventually and please, God, sleep with you." — Ruben Oliver to Polly Gray