This song marked Davis's second single release upon his departure from Bang Records to Arista, the first being "Cool Night". The style of "'65 Love Affair" was reminiscent of such blue-eyed soul groups as Hall & Oates, a vein that Davis had not explored before. Davis had originally titled the song "'55 Love Affair", but Arista felt that some modernization was needed to target an audience whose teenage years had occurred in the 1960s, including Davis himself. As Arista pointed out, Davis was only 7 years old in 1955, too young for any meaningful "love affair", but was 17 years old in 1965, perfect for the song.
Davis's previous hits had been country-oriented or ballads. The format change to pop proved to be quite marketable. "'65 Love Affair" and "Cool Night", which were recorded at the same time, ranked first and third in terms of his Hot 100 peaks ("I Go Crazy" ranked second). In spite of this popular success, Davis was so disgusted with the commercialized result that he opted out of his contract with Arista and signed with Razor & Tie Record Company, a label on which Davis never charted on the Hot 100.