Josie first bumped into Gary in 1995 at Wallingford's Bookstore, where they chatted amicably. She was aghast to discover that he was her instructor at the police academy. Gary was tough and strict, and Josie took it personally.
When Josie discovered that Gary was an alcoholic who was desperately trying to stay on the wagon, her heart softened and she began to develop feelings for him. Gary felt the same way, but because he was her superior officer, he insisted they could never be more than friends.
Eventually their desire overwhelmed them and they threw caution to the wind and embarked on a steamy sexy affair. They were forced to keep their relationship a secret because it was against regulations for fellow officers to fraternize.
After a few months the burden of arranging secret liaisons became too much and they admitted their relationship to their captain, Gabe McNamara. In response, Gabe reminded Gary of an incident in his past. Gary went deathly pale and hastily broke it off with Josie. She was determined to uncover his secret so that they could reunite.
Gary finally came clean and admitted to Josie that he was protecting her from Jackie Warren, recently released from prison. Shortly afterwards, Gary was informed that Blair had been killed and he let his guard down. But Jackie had faked her death and began spying on Gary and Josie in the guise of Herald reporter Blair Baker. She became Josie's roommate and became friends with Josie despite herself.
When Blair's secret identity was revealed, she shocked Josie with the news that she and Gary had been lovers. Now both Josie and Gary put the heat on Blair, who struck back by stalking Gary, but Josie was the one who ended up shot. During her recovery she found she couldn't aim a gun without her hand shaking. She kept this hidden from Gary for as long as she could but he was too savvy not to notice. Gary tried to help her deal with her nameless fears, but Josie dealt with them by ignoring them. She stopped taking her birth-control pills and tried to kickstart their family.
Josie's trauma continued when she was abducted by Fax Newman. She was trapped in a storm drain for several days before being rescued by Cody Murcer, an escaped con who hated cops. He held Josie for ransom, and Gary, disguised as a bum, trailed him back from the pickup site. He shot Cody and saved Josie, but wasn't able to prevent Cody then shooting Gabe and fleeing.
Josie's fears increased in the coming weeks. She had nightmares about Cody that were heightened by hang-up phone calls she was sure were from Cody. Nevertheless, Gary and Josie pushed ahead with their long-delayed wedding plans. Fearful that Cody would crash a public ceremony, they planted a false announcement in the paper and made plans to wed secretly in the Hudson barn. Grant Harrison had an agenda of his own which included saving Josie from Cody during the ceremony. He arranged for Cody's appearance at the nuptials, but was double-crossed when Cody decided all he wanted was to kill as many cops as possible.
Cody's drunken shooting spree brought a halt to the ceremony. He cornered both bride and groom in the hayloft. Facing death, Josie put her fears behind her and she and Gary both attacked Murcer, but to no avail. Gary ended up flat on his back, and it was only the intervention of Grant that saved their lives.
Sharlene was paralyzed after being shot during the confrontation. While Gary was determined to bring Grant to justice for his involvement in the barn melee, Josie told him to back off as she considered Grant a crucial part of her mother's recovery.
When Grant made an attempt on Vicky Hudson's life, the kid's gloves came off, and both devoted their efforts to nailing Grant. Gary's tactics flaunted his disregard for the rule book, and Josie found it difficult to respect him. She asked for and received a transfer to the Commissioner's office. Gary later resigned from the force rather than face punishment for the stunts he pulled on duty. He opened a detective's agency, and they both worried that no longer working together would spell the end of their closeness.
In July of 1997 they both decided that it was time for a lifelong commitment. They were married in a police ceremony on the steps of the precinct. On their wedding night, Josie broke the happy news to Gary that they were going to have a baby. That summer, one of Josie's colleagues got raped, and Josie risked her safety and her child's, in her efforts to find the rapist. When he was finally apprehended, he viciously shoved her out of an open window. After falling five stories, Josie miscarried.