<Ul> <Li> Irina Peltsin--a young Russian woman whom he sees consistently throughout the first two seasons . She is a severe alcoholic and frequently calls Tony's house when drunk, and when Carmela hints that she knows that he is seeing her, he breaks off the relationship . After her failed suicide attempt, Tony sends Silvio to give her a money compensation of $75,000 and try to reason her into moving on with her life . </Li> <Li> Gloria Trillo--an Italian - American Mercedes - Benz saleswoman with stylish tastes . Tony dates her throughout Season 3 after meeting her at Dr. Melfi's office (Dr. Melfi repeatedly expresses her disapproval of their relationship, knowing it will likely turn out a disaster). He eventually stops seeing her when she begins stalking him and calling his house, while exhibiting manipulative behaviours reminding him of his own mother (which was foreshadowed very early on when she teased him by saying "poor you", jokingly at first). He also understands through Dr. Melfi's hints that Gloria is trying to use him as a means to commit suicide (akin to the suicide by cop phenomenon). Tony asks Patsy Parisi to threaten her (he tells her that, if she tries again to harass Tony, the last face she'll see will be his, not Tony's, and that "it won't be cinematic"). It turns out that it throws her over the edge as she commits suicide soon afterwards, hanging herself . This greatly upsets Tony, who blames it on himself as well as Dr. Melfi . </Li> <Li> Valentina La Paz--a beautiful art dealer of Italian and Cuban descent, initially the mistress of Ralph Cifaretto . Tony dates her throughout Season 4 . They share a love of horses, and she visits Pie - O - My at the stable with Tony . She accidentally sets her robe on fire in Season 5 while cooking eggs for Tony . Shortly thereafter he decides to get back together with Carmela, and he breaks up with Valentina while she is in the hospital recovering from second degree burns to her head, face, and arm . Tony offers to take care of any cost related to her treatment, but their relationship ends on bad terms . </Li> <Li> Svetlana Kirilenko--the maternal cousin of Tony's ex-comàre Irina and the manager of a home care nursing business . During her childhood, Svetlana developed an osteosarcoma in her leg which was amputated soon afterwards . Tony comments that she looks like the actress Greta Garbo . She was first hired as Livia Soprano's nurse since Janice had left town . Svetlana resurfaces as Uncle Junior's nurse after he suffers a fall at the courthouse . One afternoon while Uncle Junior is asleep, Tony has sex with Svetlana on Junior's sofa but they are caught by Junior's nurse, Branca . Irina soon finds out about this and informs Carmela about the affair, prompting Carmela's violent confrontation of Tony and their ultimate separation . Svetlana later tells Tony that Branca told Irina about their affair after an argument over Svetlana's withholding Federal Insurance Contributions Act tax and other taxes from her paycheck . Tony admires Svetlana for her toughness of spirit and her refusal to allow her disability and misfortune to get in the way of her ambitions . Arguably, Svetlana is the most psychologically balanced of all Tony's extramarital affairs . </Li> <Li> Julianna Skiff--a real estate developer of Jewish descent . She meets Tony in Season 6 when offering to buy a building that he owns, to be converted into a Jamba Juice . They later begin an affair, along with a business relationship, but never consummate their relationship sexually; Tony backs off and decides to be faithful to Carmela, who stuck with him after the shooting and seemed re-devoted to him . Julianna eventually dates Christopher Moltisanti and the two begin a very destructive, co-dependent drug habit; she is last seen attending Christopher's funeral service, where she mentions that they had split up . </Li> </Ul> <Li> Irina Peltsin--a young Russian woman whom he sees consistently throughout the first two seasons . She is a severe alcoholic and frequently calls Tony's house when drunk, and when Carmela hints that she knows that he is seeing her, he breaks off the relationship . After her failed suicide attempt, Tony sends Silvio to give her a money compensation of $75,000 and try to reason her into moving on with her life . </Li> <Li> Gloria Trillo--an Italian - American Mercedes - Benz saleswoman with stylish tastes . Tony dates her throughout Season 3 after meeting her at Dr. Melfi's office (Dr. Melfi repeatedly expresses her disapproval of their relationship, knowing it will likely turn out a disaster). He eventually stops seeing her when she begins stalking him and calling his house, while exhibiting manipulative behaviours reminding him of his own mother (which was foreshadowed very early on when she teased him by saying "poor you", jokingly at first). He also understands through Dr. Melfi's hints that Gloria is trying to use him as a means to commit suicide (akin to the suicide by cop phenomenon). Tony asks Patsy Parisi to threaten her (he tells her that, if she tries again to harass Tony, the last face she'll see will be his, not Tony's, and that "it won't be cinematic"). It turns out that it throws her over the edge as she commits suicide soon afterwards, hanging herself . This greatly upsets Tony, who blames it on himself as well as Dr. Melfi . </Li> <Li> Valentina La Paz--a beautiful art dealer of Italian and Cuban descent, initially the mistress of Ralph Cifaretto . Tony dates her throughout Season 4 . They share a love of horses, and she visits Pie - O - My at the stable with Tony . She accidentally sets her robe on fire in Season 5 while cooking eggs for Tony . Shortly thereafter he decides to get back together with Carmela, and he breaks up with Valentina while she is in the hospital recovering from second degree burns to her head, face, and arm . Tony offers to take care of any cost related to her treatment, but their relationship ends on bad terms . </Li>

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