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".