After The Waterhole explodes due to a gas leak, Gaby and Philip have to work together to rebuild it. Lassiter's owner, Paul Robinson (Stefan Dennis), tires of their bickering and sends senior associate Jack Parker (Philip Parslow) to Erinsborough to sort them out and choose which one is most suitable for the manager job. Gaby works hard to impress Jack, but when she steals one of Philip's clients, Jack tells Paul that Philip should be given the managerial position. Philip insists that Gaby stays on as assistant manager and Paul agrees. Gaby begins taking flying lessons and she falls for her instructor, Jack Flynn. They start dating and when Jack admits he is a virgin, Gaby offers to have sex with him. Jack takes Gaby to Tasmania and she falls in love with him. Gaby is devastated when an ex-student of Jack's tells her that he had pretended to be virgin to get her to have sex with him years before. Jack makes advances on Lauren Carpenter (Sarah Vandenbergh) and Gaby's younger sister, Cody (Peta Brady), and Gaby breaks up with him.