"How Will I Know" is a song recorded by American singer Whitney Houston for her self-titled debut studio album. The song was released on November 22, 1985, by Arista Records as the album's third single. Originally written and composed by George Merrill and Shannon Rubicam, the song was originally intended for R&B singer Janet Jackson, but she passed on it. Houston then recorded the song with altered lyrics and production from Narada Michael Walden. The lyrics speak about the protagonist trying to discern if a boy she likes will ever like her back.

"How Will I Know" received mostly positive reviews from music critics. It became Houston's second number-one single on the US Billboard Hot 100 in February 1986, spending two weeks atop the chart and also became her first chart topper on the Canadian RPM Top 100 Singles chart. It also reached top 10 positions in Australia, Sweden, Ireland, Norway and the United Kingdom, and top 20 positions in the Netherlands, New Zealand and Switzerland.

The accompanying music video for "How Will I Know" features scenes of Houston dancing in a setting of video screens and colored partitions. The music video gave Houston exposure to the teenagers and MTV. It received two nominations at the 1986 MTV Video Music Awards; Best Female Video and Best New Artist, winning the former category. The song was performed on many of her tours including Greatest Love Tour (1986) and her Nothing but Love World Tour (2009–10). "How Will I Know" is also featured as a remix on Houston's compilation album Whitney: The Greatest Hits (2000), whereas the original single version is featured on The Ultimate Collection (2007) and I Will Always Love You: The Best of Whitney Houston (2012).