The lyrics largely revolve around the aftermath of the relationship that was the inspiration for 24 Hour Revenge Therapy; others, such as "Save Your Generation" and "Chemistry", deal with slacker culture and attending school, respectively.

Unlike previous releases, Dear You sees Schwarzenbach sing more instead of scream: his vocals evoked Morrissey, while the overall band was compared to the work of Green Day, Jawbox, and Nirvana.

[6] Journalist Dan Ozzi, in his book Sellout: The Major-Label Feeding Frenzy That Swept Punk, Emo, and Hardcore 1994–2007 (2021), said the material on 24 Hour Revenge Therapy strengthened the audience's relationship to Jawbreaker, which in turn made their live performances more intense.

The band were already being criticized for touring with Nirvana sometime prior, as well as for dropping their earlier material from their live shows and Schwarzenbach's voice changing as a result of throat surgery.

[37] Schwarzenbach did 12-hour days on guitar tracks and vocal takes with Cavallo; Givony compared this working methodology to Billy Corgan on the Smashing Pumpkins' Siamese Dream (1993) and Kevin Shields on My Bloody Valentine's Loveless (1991).

[38] After trial and error, Cavallo created what he referred to as a White Hot Sound recording technique to track Schwarzenbach's playing, whose style relied on open-string riff parts.

[37] Cavallo layered three different guitar tones, which Ozzi said made an audio mixture crafted "to be so thick and rich that it would knock the listener over and carry them off on a tsunami wave of distortion.

Ozzi felt that Schwarzenbach's new method was "understated and subdued, replacing the occasional bark with a brooding rumble", which was closer to former Smiths frontman Morrissey, rather than hardcore punk vocalist Ian MacKaye.

Givony said these two tracks evoked the work of Built to Spill, Spiritualized, and Swervedriver instead of the Jawbreaker that made their debut album Unfun (1990) or 24 Hour Revenge Therapy.

[34] Following the release of Bivouac, the band received a letter from a friend that stated, "you can't dance to pain", which Pfahler loved and wanted to name Dear You that instead of its final title.

Previously, the energy of performing was the driving factor of the band's creativity; Schwarzenbach found it difficult screaming constantly as he explained: "I had to live the part of the brute in order to sing about it".

[34] In a retrospective review for Gibson, writer Jonah Bayer said the song exemplifies the album's sound: "a melodic pop sensibility that's augmented with buzzing Les Pauls, driving drums, and [...] Schwarzenbach's signature one-liners".

[55] Michael Nelson of Stereogum wrote that in "Accident Prone", Jawbreaker emulated the "weight of a thousand guitars to hammer home a battering ram of a chorus and a stellar, sweeping bridge", with its big sound "heightening the intensity".

'"[73] "Friendly Fire", which acts as a musical bridge between Dear You and its predecessor,[44] deals with Schwarzenbach's paranoia around signing to a major label and seeing it as a fight for survival.

Ozzi said Cavallo's production style helped to round out the song's rougher exterior, making both Schwarzenbach's guitar and vocals "pop with a warm lucidity.

[79] Ozzi noted similarities between it and the Green Day clips, in particular, the choice to have three men playing a song in a tiny room, offset by a saturated colour scheme.

[91] In Jawbreaker's home base of the San Francisco Bay Area, they were banned from punk club 924 Gilman Street, who had previously barred Green Day, for their association with Geffen Records.

[16] In December 1995 and January 1996,[95] they toured Australia as part of the multi-day Summersault festival, marking their biggest shows in their career to individual crowds over 10,000 each,[39] ultimately playing to 50,000 collectively.

AllMusic review Tim Sendra wrote that it was a "sleek, slick punk-grunge classic that relies as much on clever songwriting and restrained emotions as it does on the group's trademarked high-energy attack".

[109] PopMatters' Jon Goff was indifferent to the music, as "what was once widely considered watered-down punk now sounds more like harmless alternative radio",[72] and Tom Sinclair of Entertainment Weekly said it "isn't quite as stellar" as earlier albums, though it manags to surpass the majority of their contemporaries.

The new sound is gauzy and soft; it's Jawbreaker, cough-syrup style", and negatively compared Schwartzenbauch's guitar tone to Green Day's, making the tracks "suffer considerably".

[61] Greg Beets of The Austin Chronicle went on further, saying that Cavallo's "flat production castrates the band" and the "sad result is one of obfuscated talent in the name of radio friendliness", which Pitchfork writer Christopher Sebela agreed with.

[61] Brian Howe of The Fanzine viewed it as a "vibrant, realized mature album" that showcases "rather ingenious wordplay",[46] while Sinclair said the "literate lyrics" made them the "thinking person's Green Day".

[70] Julie Gerstein of Punk Planet noted that it was "filled with Schwartzenbauch's raspy, sad vocals and charged, emotional (but not emo) lyrics, Dear You encapsulates the hurt and cynicism of a break-up like nothing else".

[29] The "Into You Like a Train" cover, alongside previously unreleased outtakes "Sister", "Friendly Fire" and "Boxcar", were included on the band's sole compilation album, Etc.

[108] Pfahler explained that his participation in this edition amounted to the song selection and design, as the staff at Revolver Distribution and PR company Hopper did the rest of the work.

[132][133] Some of the band's detractors erroneously blamed Schwarzenbach's surgery as being the core issue, pointing out the change in vocal style in the year between 24 Hour Revenge Therapy and Dear You.

[136] The Billboard staff wrote that the punk scene grew in the years following; unlike Green Day and the Offspring, MTV had not yet embraced the emo music that Jawbreaker was performing.

[29][138] Gross said some of the lyrics on Dear You foreshadowed the "youthful nookie anxiety of your average Drive-Thru band", while others were "beating Chris Carrabba [of Dashboard Confessional] to the passive-aggressive punch by five years".

[142] Ryan Ritchie of OC Weekly said the title of "Sluttering (May 4th)" gave birth to Jawbreaker Day: the band has a "devoted fanbase and the Internet is prime real estate for nerds doing nerdy things.