it "navigates the fine line separating sweet from saccharine". Spin staff member Andrew Unterberger called "Dilemma" a "puppy-love duet", while Blender staff described the song as a "capable ballad". However, Soren Baker of the Chicago Tribune stated that the "pseudo-ballad" lacked spunk and was "hardly worth the bother". Writing for The Washington Post, Arion Berger critiqued that the "neo-R&B" song was a "requisite lull" in his review of Nellyville. "Dilemma" won a Grammy Award for Best Rap/Sung Performance at the 45th Annual Grammy Awards on February 23, 2003. Commercial performance "Dilemma" debuted on several Billboard charts on the week of July 6, 2002, at numbers 66 and 63 on the Hot R&B/Hip-Hop Songs and R&B/Hip-Hop Airplay charts respectively. The next week, it debuted at number 51 on the Radio Songs chart, as well as at number 53 on the Hot 100 during the same week. After four weeks, on the issue dated August 17, 2002, "Dilemma" peaked at number one on the Billboard Hot 100, where it stayed there for 10 weeks and remained on the chart for 29 weeks. With this song, Nelly replaced himself from the top of the chart, as his previous single "Hot In Herre" dropped to number two while "Dilemma" ascended from number two to number one. This surprised Nelly's record label, as they did not expect the song to instantly become popular and did not film a music video during its release. "Dilemma" topped the Mainstream Top 40 chart on the week of September 21, 2002. The song was ranked at number 11 on the Billboard Hot 100 decade-end list from 2000 to 2009, and placed at the number 75 position on the listicle of all-time songs to chart on the Billboard Hot 100. On the UK Singles Chart dated October 26, 2002, "Dilemma" topped the chart, where it remained at the position for two weeks, before charting for 24 total weeks. The song sold 208,000 copies in the first week and 129,000 copies the following week, which prevented Justin Timberlake's 2002 debut solo single "Like I Love You" from the number one position. It was the fourth-best selling single in the United Kingdom in 2002, and was the 23rd highest-selling single in the country from 2000 to 2009. As of October 2016, "Dilemma" is the most successful song in both Nelly and Rowland's discographies. As of February 2021, the song has sold over