Having made an impression with his performance in the 1940s talent show, Gary is signed up by Sidney Wix to perform around London. Gary's nerves aren't helped by the late night performances in rough areas, coupled with his promotion to lead actor in Yvonne's play. The pressure increases when Sidney Wix offers Gary a lucrative contract to sell "his" songs to recording artists, a deal Phoebe believes will provide them with a terrific future.

Yvonne thinks she may be pregnant, putting more strain on Gary's already frayed nerves. When Yvonne goes to her parents for the weekend, Gary joins Phoebe on a trip to the countryside to visit her young cousins, who have been evacuated. Spurned on by interest from an American man serving with the British, Gary takes his relationship with Phoebe to the next level.

Phoebe receives an unexpected letter from the brewery saying they have another tenant for the Royal Oak and she has to leave. George Harrison, the brewery's sleazy representative says if she lets him stay in her spare room and provides "special favours", then he'll make sure she keeps her tenancy. In 1995, Gary campaigns to stop building in Duckett's Passage which could severely impact his ability to travel back to the 1940s.