Most of Jack's storylines were central to his on-off relationship with Martha MacKenzie (Jodi Gordon). Viewers saw the couple go through marriage, divorce, a second marriage and Martha being widowed. Martha and Jack's first marriage is cut short because they argue to much, Martha leaves Jack. They start to lead separate lives, but Jack is there for Martha after she has an abortion, Martha who is feeling low at this point kisses him, Jack's girlfriend Sam Tolhurst (Jessica Chapnik) sees this. Of the situation during an interview with Yahoo, O'Brien stated: "I think Jack felt like "Oh this is nice, but I've moved on, I've finally moved on and found someone, but deep down he still wants Martha." O'Brien added that he believes Jack was always in love with Martha, even whilst with he was in a relationship with Sam. Both O'Brien and Gordon agreed that when Jack and Martha first broke up it was a bad time for Jack, as his life was spiraling out of control, he needed her, but she left him when he needed her the most. They later become friends in an unlikely turn of events, O'Brien believed it hard to understand how Jack could be so forgiving towards her.