Originally, another song was to be released as the second single, "For the Love of You," but Arista Records decided to release "Didn't We Almost Have It All" instead because all Houston's singles had to be original material at this point of her career.
Rob Wynn of Allmusic highlighted the song. L.A. Times editor Robert Hilburn wrote: "Houston's stardom will be boosted most by "Didn't We Almost Have It All," a sweeping Masser-Will Jennings ballad with the kind of big, emotional finish that will make Liza and hundreds of other singers wish they had been given first crack at the song. I'll save my champagne for pop singers who don't add that overblown song to their repertoire." Rolling Stone's Vince Alleti wrote: "Masser reprises the show-tune schmaltz of "The Greatest Love of All" in his even cornier "Didn't We Almost Have It All." According to Whintey fanpage: "But there is a cut on the album whose title inadvertently sums up Houston at this stage of her development -- "Didn't We Almost Have It All." St. Petersburg Times editors Eric Snider and Annelise Wamsley described "Didn't We Almost Have It All," as "an overblown tune co-written by Michael Masser (...) that finds Houston stripped of subtlety - with her wire-to-wire belting, you can just see the fetching songstress looking skyward, arms outstretched." Following Houston's death in 2012, Entertainment Weekly published a list of her 25 best songs and ranked "Didn't We Almost Have It All" at number 16 because "so transformative was Houston's voice that she was able to make lite-FM ballads like this one sound effortlessly rich and melancholic".
It debuted at number forty one on the Hot 100 the week of August 22, 1987 and six weeks later reached number one. "Didn't We Almost Have It All" reached number one on the Billboard Hot 100 for two weeks, from September 26 to October 3, 1987, where the song became her fifth consecutive number one. The song also topped both component charts, the Hot 100 Singles Sales and Hot 100 Airplay, Houston's fourth song (and fourth consecutive release) to do so. The single stayed in the Top 40 for 13 weeks, and topped the Billboard Adult Contemporary Charts for three weeks. It has sold over one million copies World Wide.
"Didn't We Almost Have It All" was ranked 22nd on the Billboard Hot 100 year-end charts (1987), and remained in the Billboard Hot 100 for 17 weeks. It was her fifth number one single on the Billboard Hot 100, her fourth on the Billboard Hot 100 Singles Sales, her fourth on the Billboard Hot 100 Airplay, and her fifth on the Billboard Adult Contemporary Charts.