The song is rumoured to be a tribute to teenaged London pirate radio comedian Mark Gould whom Bananarama subsequently demanded as their Christmas present for 1983 on the Christmas edition of BBC1's Show Business programme, which was broadcast on 16 December 1983.
Released in summer 1982, "Shy Boy" became the third consecutive single by Bananarama to hit the top-five, reaching number four in the UK singles chart. It also was a success in Australia, where it reached number two, becoming their first top 40 hit in that country. Top-ten success also followed in New Zealand and Canada. "Shy Boy" charted well on the U.S. Hot Dance Club Play chart and was the first of Bananarama's singles to dent the Billboard Hot 100, peaking at number eighty-three. The song was known as "Shy Boy (Don't it make you feel good)" in the USA.
The song was originally called "Big Red Motorbike", however Bananarama didn't like the lyrics and changed it to "Shy Boy".
The music video was directed by Midge Ure and Chris Cross who were then members of the group Ultravox. It featured the girls giving a nerdy guy a make-over, turning him into a stud. When his new look attracts the attention of a sexy secretary, the girls get revenge by dousing him with a bucket of water. The nerd-turned-stud was played Terry Sharpe, the lead vocalist of the Northern Irish rock group The Adventures, who was Sara Dallin's boyfriend at the time.