[3] Lyrically, "Diggin' on You" depicts a boy hooking up with a girl "chillin' with [her] Kool-Aid in a park",[1][15] with Lynn Ford of Indianapolis News opining that it has "a romantic aura steeped in young love".

[3] Several "Diggin' on You" remixes were released, which Billboard commented ranged from a live brass version with jazz-inspired horns, to a pop and house hybrid.

Mackintosh's mix to be "slick [and] smooth" and sonically similar to Roy Ayers, the Untouchables production to contain a "darker hip hop" atmosphere, and compared the tone of Soulshock's remix to R.

[18] Writing for The Guardian, Ross Jones praised Babyface's "sultry" production on "Diggin' on You" and opined that monks would be "comely" intrigued by TLC's "dirty phone-call" vocals.

[19] Chuck Arnold of Philadelphia Daily News stated that the song is one of three tracks on CrazySexyCool to be "radio-ready",[2] while Langston Wertz Jr. of The Charlotte Observer and Cheryl Jackson of The Tampa Tribune considered "Diggin' on You" to be "sexy (and memorable)" and "laid-back" respectively.

It's nice in a summery way but the real TLC chart action won't happen until the re-release of 'Creep' at the beginning of next year.

[18] While reviewing the European 12-inch single of "Diggin' on You", James Hamilton of Record Mirror described Eddie F's remix as "slinky rolling" accompanied by the TLC members' "husk[y]" and "[coo]ing" vocals, Soulshock's production as "delicately weaving", Mackintosh's mix as "chunk[y]" and "jiggling", and the Going Home Dub as "repetitive stuttery cantoring".

[24] The song received a gold certification by the Recording Industry Association of America (RIAA) on January 3, 1996, for selling 500,000 copies in the US.

[31] An accompanying music video for "Diggin' on You" aired on MTV in October 1995, after "Kick Your Game" was sent to radio stations and TLC's management needed another song to be promoted as its replacement.

[8] American musician Sevyn Streeter performed a cover version of "Diggin' on You" as an a cappella on YouTube, which Da'Shan Smith of Billboard declared as "soft-rock&B".

Smith additionally compared "Diggin' on You" to Streeter's 2013 song "It Won't Stop", noting that both contain lyrics regarding "an endless infatuation with a lover".