The video was filmed on location at a beautiful modern house in Malibu, California. Art director Stephen Rice suggested a waterfall be constructed on site to use as both a backdrop and to shoot through.
Will Smith was just starting to date Jada Pinkett at this time. He hung out on location all day to give his encouragement and support.
"How Many Times" was Jada Pinkett Smith's directorial debut. She also co-wrote the video treatment and co-starred with Gerald Levert.