In the second single from Bananarama's debut album, the English pop trio turns a shy boy into an ideal lover who "knows about a good time" and "gives me lovin' like nobody else." The song marked their first collaboration with songwriters/producers Steve Jolley and Tony Swain, who went on to helm their next two albums, but it was a rocky beginning. Like their previous single, a cover of the Velvelettes' "He Was Really Sayin' Somethin'," Bananarama was working a Motown vibe in "Shy Boy," but the pop singers weren't interested in being a modern-day Supremes. The group's Siobhan Fahey explained: "[Jolley & Swain] wanted us to do their songs, not ours. They wanted a 1980s version of the old girl groups, disembodied voices. They didn't see us as voices with ideas."
Midge Ure and Chris Cross of the British new wave band Ultravox directed the music video, which finds Bananarama turning a nerdy office worker into a leather-clad hunk. The group's Sara Dallin enlisted her boyfriend, Terry Sharpe of the Irish rock group The Adventures, to star in the clip.
Once this hit the UK charts, the girls were no longer able to remain anonymous. Dallin told Smash Hits in 1983: "After 'Shy Boy' was really successful, we were recognized all the time. I remember once on the Number 8 bus coming back from Top Shop, these little kids behind us started singing 'Shy Boy' and it was really embarrassing. That's the first time it ever happened."
This was used in the 1985 comedy Fraternity Vacation, starring Tim Robbins.