21 Questions

The second single was a break from the album: an R&B-influenced love song about a series of questions to an unnamed girlfriend, with elements of Barry White's It's Only Love Doing Its Thing. Dirty Swift of Midi Mafia produced it, Dre mixed it, and Nate Dogg sang the chorus. Dre did not want it on the album. 50 Cent said he was two people and always had been, and that it was necessity, not diversity. He has cited LL Cool J as the inspiration for writing it. In 2023 he said it and Many Men were the two songs he hesitated over because they were slower.

It reached number one on the Hot 100 in May 2003 for four weeks, after In da Club. It also spent seven weeks at number one on the Hot R&B/Hip-Hop Songs chart. It reached the top ten in the Netherlands, New Zealand and the UK, and the top five in Canada and Australia. In the video, directed by Damon Johnson, Dr. Dre and Phillip Atwell, 50 Cent is arrested and jailed, and his girlfriend, played by Meagan Good, tries to keep in touch while Tyson Beckford plays a rival inmate. The prison turns out to be a scenario that a worried 50 Cent imagines at home. It reached number one on TRL two days after its debut at six.