In 1963, Asher interviewed The Beatles. A photographer for the BBC's Radio Times asked them to pose with Asher . Asher subsequently commenced a five-year relationship with McCartney, getting engaged in 1967. She inspired many of McCartney's songs, such as "All My Loving," "And I Love Her," "I'm Looking Through You," "You Won't See Me," "We Can Work It Out," "Here, There and Everywhere," and "For No One" (all credited as Lennon/McCartney). Lennon/McCartney penned the number one hit "A World Without Love" for her brother Peter.
McCartney stayed in the Asher family home at 57 Wimpole Street from 1964-66 and wrote several Beatles songs there. He wrote in a room usually used for music lessons. The Asher house was also a place of intellectual stimulation for McCartney. He enjoyed the rarefied atmosphere of upper-middle class conversation and company that the house afforded, and to which he aspired, According to Cynthia Lennon, McCartney was "as proud as a peacock" to have Jane as a girlfriend, and saw her as "a great prize." Marianne Faithfull remembered McCartney and Asher "never getting on very well," and described one evening at Cavendish Avenue when McCartney wanted a window to be open and Asher wanted it shut. McCartney would repeatedly get up and open the window and then Asher would get up and close it, although neither of them made any comment about it during the whole evening.
McCartney did not stop having one-night stands with other women during his time with Asher, because he felt that since they were not married, it was allowed.[10] On 25 December 1967, McCartney and Asher announced their engagement, and she accompanied McCartney to India in February and March 1968. Asher broke off the engagement in early 1968, after coming back from Bristol to find Paul in bed with another woman, Francie Schwartz. They attempted to mend the relationship, but finally broke it off in July 1968. Asher has consistently refused to publicly discuss McCartney or her time with him, and has maintained her position on the matter to this day. On this basis, she is described by the Beatles' 1968 biographer Hunter Davies as the only major Beatles associate not to have published her recollections.