town looking for Paul Cramer (David Tom), a man Natalie begins a friendship with and John is leery of. Katherine wants to recover money stolen from the Santi organization she believes Paul has. Paul no longer has the money, and is pressured by John to testify against the Santis. Later, it is discovered by John and his brother Michael that Paul is being paid under the table by the chief of staff, Dr. Long to transport black market organs. John tries to discourage Natalie's involvement with Paul but despite John's numerous warnings, Natalie's friendship with Paul develops into a light hearted flirtation. John begins to struggle with his feelings for Natalie again, and letting go of his past with Caitlyn. John begins to allow himself to get closer to Natalie. On May 11, 2004, Natalie takes off with Paul to Atlantic City. An upset John follows. When John finds Natalie, he's unable to verbalize why he has followed her and she becomes upset and tells him, Paul is offering her fun, what can he offer her. In response, John kisses Natalie. When Paul interrupts, John tells Natalie he's heading back to Llanview and asks if she'll join him. Natalie accepts John's offer and apologizes to Paul for leaving. John and Natalie end up in bed together, but Natalie stops them from making love because she feels John has not moved on from Caitlyn and doesn't want to be a stand in for a ghost. John remarks maybe she's the one with the ghost, referring Cristian. Natalie, in a gesture to prove she is moving on from Christian, removes her wedding ring. Natalie tells John, she saw his drawer filled with memories of Caitlyn, and he is still holding onto her. Natalie leaves, and despite John's request she wait on him, she later heads back to Atlantic City to see Paul. John, wanting a relationship with Natalie, finally lets go of Caitlyn. The timing is again off, as Natalie becomes stressed with her mother's heart transplant, and being accused of murdering Paul Cramer. John supports Natalie through these crises, but the two do not become a couple. After, her mother's recovery and Paul is discovered to be alive, Natalie wanting a change leaves town with Paul in search of the Santi fortune. After a few encounters with Evangeline, John and Evangeline sleep together while trapped in a basement. Evangeline breaks up