[3] In determining which tracks to include, Rapsody expressed that she wanted to prioritize more personal material so that listeners would best understand her: I told myself that I haven't really introduced myself to people yet.

[5] Please Don't Cry is an introspective album on which Rapsody explores a variety of topics, such as "sexuality, identity, self-preservation, and the plight of Hip-Hop artistry".

[6] The album employs a framing device where Rapsody portrays herself as attending a therapy session; the therapist, voiced by Phylicia Rashad, appears on the opening track "She's Expecting You" and several subsequent occasions.

[7][8] The principal elements of the album's instrumentation have been identified as "warm bass, crisp percussion, heavenly background vocals, and light chords".

[2]In contrast to the more reflective mood present on much of Please Don't Cry, "Raw" has been identified as a more "hard-hitting", lyrically driven track; similar descriptions have been applied to "Black Popstar" and "Asteroids".

[9] Rapsody has stated that her goal with "Lonely Women" was to emphasize the wide variety of ways in which one can discuss sexual topics, and to showcase her own preferred approach to the subject matter.

[2] The song "A Ballad for Homegirls" includes a feature from Baby Tate[10] and reflects on the challenges of "yearning for an emotionally unavailable man".

Danilo Castro of HotNewHipHop stated that "listeners will be rewarded" for paying close attention to the album,[6] and Robin Murray of Clash remarked that it "just might stand as [Rapsody's] most complete work yet".

[10] In particular, Rapsody's emotional openness received commendation: Gary Gerard Hamilton of the Associated Press described the album as "entering a new territory of unapologetic vulnerability",[3] and Pitchfork's Stephen Kearse called it "a vivid affirmation of self and community".

[9] Rapsody's performance achieved acclaim as well, with Kearse stating the opinion that she showcased "all the flows, cadences, and deliveries she's mastered" over the course of the album.

Nevares felt that the prevailing mood of the production was "calm cohesion" that "highlight[ed] subtle instrumentation in ways that more complicated beats would overshadow".

[9] Kearse praised the "lush blends of R&B, gospel, reggae, and trap", and elsewhere compared its sonic palette to The Miseducation of Lauryn Hill and to Dungeon Family artists.

Castro felt that tracks like "Black Popstar" employed "hard-hitting instrumentals that liven things up",[6] but Nevares criticized it as "trite trap drum sequencing".