Jenny grew up with Jackie Estacado at St.Mary's Orphanage. While Jackie was often rejected by the orphanage staff for his anger issues and disobedience, Jenny comforted him and remained his one true friend, occasionally sneaking off to see him during punishments. The two eventually fell in love and began a serious relationship before the events of The Darkness, though Jackie does not reveal his career as a criminal to her. However, when he does express violence in front of her (in some cases, to defend her honor,) she rejects him and does not accept this behavior. She refers to Jackie as "ratface," a nickname he seems to accept despite its sarcasm and his general no-nonsense attitude.
Jenny is a slim female, with piecings on her bottom lip. In the first game, she is depicted wearing long jeans, a green sweater, black shoes and a red scarf.
Jenny Romano is Jackie's girlfriend in The Darkness, first appearing for a celebration of Jackie's 21st birthday in her new apartment. She is voiced by Lauren Ambrose. As he comforts her during their TV session, Jackie and Jenny share a number of simple intimate moments, allowing the player to understand their chemistry. Throughout the game, Jenny acts as a sort of muse for Jackie to keep living. It is made apparent that the two deeply care about each other.
Jackie's Uncle Paulie takes Jenny captive as a bargaining tool once Jackie begins to fight back against Paulie's mob. Paulie executes her in cold blood in front of Jackie, leaving him heartbroken. Jenny leaves Jackie with one final line: "Jackie, this isn't your fault..."
Jenny's death leaves Jackie furious: Johnny Powell states in The Darkness II that "Not only did Jackie have nothing left to live for, but he also had nothing left to lose." Jackie decides to kill his Uncle Paulie in an effort to take revenge for Jenny's sake. Unsurprisingly, the man with an unspeakable eternal evil in the form of two monstrous tentacles manages to succeed.
Her final appearance is at the end of the game when she comforts Jackie from beyond. In this scene, Jenny absolves Jackie, asking him, "How can I forgive you if it wasn't your fault?" This delineates her as a pure being.
Between The Darkness I & II
Horrified by The Darkness's ability to corrupt, Jackie contains The Darkness within himself and does not allow its power to employ itself. During this time period, he hallucinates, seeing and hearing Jenny as he lives his day-to-day life. It is apparent at the beginning of The Darkness II that he has not found a way to maintain a healthy relationship; he also lights a candle for Jenny every night, next to a headshot of Jenny.
During this time, The Darkness claims Jenny's soul, intending to use it as a bargaining tool to convince Jackie to do what it wants.
The Darkness II
Jenny appears multiple times throughout The Darkness II, both as a hallucination and as a soul captured by The Darkness. She is voiced by Stefanie E. Frame.
Jackie is forced to release The Darkness after an attack on his mob while at a restaurant. The hallucinations Jackie has become more vivid, including an extremely vivid hallucination of the night before Jackie's 21st birthday at the restaurant where Jenny works. The Darkness warns against these hallucinations, claiming that " 'It' deceives [Jackie]."
When Jackie almost dies after one hallucination, he finds himself in a mental health hospital; he is one of the patients, along with most of his gang's members serving as hospital staff or fellow patients. Jenny serves as his psychiatrist here, attempting to dispel Jackie's "hallucinations" in which he finds himself to be a mob boss, wields The Darkness, and is dating Jenny. She seems frustrated with Jackie's case, unable to cope with his constantly shifting fantasies; she claims that a year ago, Jackie believed he was in the British Secret Service. These hallucinations continue throughout the game; eventually, this asylum is revealed to be a sort of purgatory created by The Darkness to confuse Jackie while it is piecing his body back together, keeping him from dying.
Jackie is eventually confronted with an offer he can't refuse; to give The Darkness to the ancient organization The Brotherhood. Jackie is inclined to accept, but The Darkness reveals that it has claimed Jenny's soul and will torture and destroy her if Jackie does not do as it wishes. Jackie decides to keep The Darkness in an effort to protect Jenny, and his battle with The Brotherhood and other hallucinations continue. Jackie eventually claims a mystical object known as The Siphon, an object powerful enough to kill him and allow him to enter hell and fight The Darkness for Jenny's soul. Jackie resists the asylum world, descending into Hell, where he finds Jenny and frees her from The Darkness's grasp.
Jackie and Jenny spend what they believe will only be a few moments together before they are both disposed of and sent to hell. However, Jenny apologizes to Jackie, at which he is confused; suddenly, she is driven back, and she transforms into The Angelus, the eternal enemy of The Darkness. The Angelus, now possessing Jenny's body, leaves Jackie alone in hell while taking Jenny back to Earth. When Jenny is possessed by the Angelus, she is voiced by Anastasia Baranova.