Once Prue came into her powers, she invariably became involved in criminal cases involving murdered, missing, or otherwise harmed innocents. This led her to reunite with her highschool sweetheart, Andy Trudeau, who had become an inspector with the SFPD. Their feelings apparently rekindled, they began dating again. On their first date in years, they end up picking up just where they left off (sleeping together), but afterwards, decide to slow it down. The relationship was turbulent - Prue's secret witchcraft caused a lot of difficulties. She was regularly late or a no show for dates and appointments with Andy, much to his frustration, and even more frustrating for Andy was Prue's inexplicable involvement in his cases, causing him to start a file containing his own hypothesis which was startlingly accurate.


Prue and Andy Truedeau share one last kiss in "Deja Vu All Over Again"Eventually, Prue cast a truth spell on Andy without his knowledge, whereby 24 hours later, he would remember nothing from the past day. She used this to tell him the truth about herself to see if he could accept it. In the last three minutes of the day before the spell ended, he could not tell her that he could overcome it because he wanted a normal family, and so she called the relationship off. Andy grew hostile toward Prue after her many involvements with his cases without explanations. He finally caught her using magic to fight a demon, and she was forced to tell him everything Andy was in a state of shock for a long time, but his feelings hadn't change since he was under the truth spell: he still wanted a normal life with a normal family, and nothing to do with magic. Prue accepted this, and they remained close. Despite the lack of a romantic relationship, Prue and Andy still loved each other deeply. Things looked hopeful, but at the end of season one Andy dies to save Prue. Andy's spirit visits Prue in a dream, assuring her that his death wasn't her fault, and that it was meant to be. While Prue initially accepts this, her viewpoint changes with grief. She soon begins to think there is no use to being a witch if she cannot save her loved ones from evil. Piper and Phoebe reminded her that she warned Andy to stay out of harm's way, but he chose to get involved, and he died a hero.

After Andy's death, Prue dated a coworker, an irritaing, unorthodox, very anti-Andy character named Jack Sheridan. At one point, she suspected he was a warlock when she believed she saw him in two places at once. Turns out Jack has a twin brother, who was impersonating Jack for fun. Though she hated him at first, he won her over with his charm. Jack helped her loosen up and stop taking herself so seriously, but when his lack of professional ethics and immaturity did not match up to where Prue wanted to go with her life, she broke it off with Jack. Another involvement, though not a relationship, was with crime boss Bane Jessup under the guise of being an assassin, and later when he kidnapped her to get her to help him clear his name. The relationship was based on sexual heat and short-lived, more of a flirtation than anything else.