For an offender on the Violent Criminal Database, The Blacklist's Jolene/Lucy Brooks is certainly turning on the charm for Tom Keen.

Raymond 'Red' Reddington (James Spader) won brief access to the FBI's database during "General Ludd," and the master criminal used that time to search for a Lucy Brooks (Rachel Brosnanhan). From the look of disgust on Red's face when he viewed her record, Lucy may have had some personal involvement in Red's life and he is clearly someone he is not particularly fond of.

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However, viewers did not get to truly meet Lucy until she appeared as Jolene during Monday's airing of "The Alchemist." Posing as a substitute teacher from Tom's (Ryan Eggold) school, Jolene quietly positioned herself in the Keen's lives at a volatile moment by attending their baby shower.

While Liz (Megan Boone) and Tom argued about maternity leave and Tom became ever more frustrated with his wife's job and her long hours away from home, Jolene managed to ensnare Tom's interest enough that he decided to attend an art function with her when Liz cancelled on their plans.

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"[Jolene is] care free, easy going, unburdened by the kind of things that burden Liz and that is going to be tempting for Tom," explained executive producer John Eisendrath in a Beyond the Blacklist featurette. "All the while, we hope that the audience will be wondering, 'Wait a second, who is she for real? Is she someone who should be trusted or not trusted?' She clearly has something that she is keeping secret."

Learn more about Jolene, Tom's wavering fidelity, and Red when The Blacklist airs Mondays at 10 p.m. ET on NBC. Click the video below to see a preview of next week's episode, "The Cyprus Agency," and click here to view episode stills.