The song received widespread critical acclaim from music critics; many compared it to a
Prince composition.
Entertainment Weekly called it "insidiously, almost obscenely hooky: a slithering riff on early-'80s Prince with a monster synth line." Rob Sheffield of
Rolling Stone stated that "The superb Prince hommages, "Try Sleeping With a Broken Heart" and "This Bed," are experiments that pay off big, submerging Keys' pipes in unabashed 1980s synth cheese." Andrew Burgess of
MusicOMH referred to it as a "fever dream", citing it as a "standout moment" while Clover Hopes of
Vibe magazine praised the song as "instantly timeless" and described it as a "gorgeous drum-powered exercise in vocal discipline (with its whispered huffs and puffs) that deals with the loss of a man's mere presence". Dan Weiss of
Popmatters, gave the song a seven out of ten rating and thought that ""Sleeping" is proof that Keys can find the warmth inside of a song even when she pushes away from the piano and the arrangement drifts into something colder and more abstract." Randy Lewis of the
LA Times was highly impressed with the track and wrote: "In "Try Sleeping With a Broken Heart," she's crafted an intriguing refrain: "I'm gonna find a way to make it without you . . .," admitting she's still searching for a full-fledged sense of security in whatever newfound freedom she's come into. But then she extends the thought with the kicker word ". . . tonight." Is she taking the one-day-at-a-time approach of a 12-step program for romantic addiction? Is it merely the application of an emotional band-aid? Or might she be asserting that the path to true independence always begins right here, right now? It's never entirely clear, and the ambiguity makes the song that much richer.".
PopJustice said that the song is the album's "secret weapon" and called it "amazing", adding that it's "a head-explodingly brilliant, timeless 'n' modern
R&B ballad".
Slant magazine said that "The best moments on Freedom come early, with the clear standout being "Try Sleeping with a Broken Heart." There, some retro synth work lends a funky backdrop for Keys's breathy vamping, alternating disco-diva choruses with Prince-worthy verses". Robert Copsey of
Digital Spy gave the song four out of five stars, branding it as one of the stand out tracks from the album. He also stated that the verses were good because of Keys's breathy vocals with military-style drumming in the background, he felt the chorus was full of "palpable emotion". Overall, he branded the song as an "effortless and timeless power ballad". ==Music video==