"Show Me the Meaning of Being Lonely" was nominated for a Grammy award on the 43rd ceremony for Best Pop Performance by a Duo or Group with Vocals, but lost it to Steely Dan's "Cousin Dupree". Emily Exton of "VH1" placed the song at number seven on their "20 Backstreet Boys Songs" list, writing that the song is "a more mature sound that showcased Kevin’s vocals instead of mostly his dark and mysterious looks. Here the Boys tackle grief surprisingly well, without pouring on too much schmaltz or over-complicating things." Danielle Sweeney of "The Celebrity Cafe" also placed it at number seven on her "Top 10 Backstreet Boys Songs", writing that, "it's their most emotional song, containing the lyrics, 'how can it be you’re asking me to feel the things you never show?'. Deep, guys."