Julianna Skiff
Julianna is from Binghamton, New York and her parents own a catering business. She left home at seventeen because she said she didn't want to make Salisbury steak for the next twenty years. She nearly became Tony's new mistress as he recovered from his gunshot in 2006. They met because she was a realtor working for Century 21 and trying to purchase a building owned by Tony (Caputo's Poultry) in Newark, New Jersey. She was persistent in pursuing the deal, contacting Tony at Satriale's and the Bada Bing and over the phone. At the Bada Bing Tony first made a pass at Julianna but she told him she was going to exercise self-control and decline because she was engaged and everything was going well for her. Despite some misgivings eventually, her third offer was high enough for him to accept the deal; Tony arranged to meet her at home to sign the papers. When he arrived, they got business out of the way and immediately started kissing and began to undress one another. When the undressing reminds Tony of Carmela's devotion in taking care of him after his gunshot wound, Tony abruptly ends the encounter and walks out. Tony later spotted Julianna on a ride at the Feast of St. Elzéar but failed to get her attention.
Following her rejection by Tony, Julianna went to an AA meeting. There, she met Christopher Moltisanti who was also in attendance and who remembered her from when she first approached Tony at Satriale's. He introduced himself after the meeting and invited her for coffee which prompted the beginning of an extramarital affair with Julianna. Tony reinitiated his pursuit of Julianna when they met to close the Caputo's poultry real estate deal and she was initially polite in declining any further contact with him. He arranged to meet with her on the basis of starting another real estate deal and this time she was more angry in rejecting his advances.
Despite warnings from both of their sponsors, (Christopher and Julianna's relationship was enabling for the two recovering addicts) they began smoking heroin together. Christopher revealed to Tony his relationship with Julianna to avoid him investigating for himself and discovering their drug use. After a conversation about Christopher's disappointment with his life in organized crime (because of failure of others to live by the code of omertà), and their return to drug abuse, Julianna worried their relationship was ending and suggested they attend a meeting together. In episode "Kennedy and Heidi," she attended Christopher's wake, encountering Tony and Carmela together as she came to pay her respects, where Tony accidentally introduced her as "Julianna Skiffle".