The music video for "Strawberry Kisses" was directed by Mark Hartly. The video features Webster entering a space ship and meets up with a computer animated character called Digital Jimmy. Digital Jimmy (DJ) was created by Hartly, and Webster thought the idea was fantastic and when she saw the basic drawing she fell in love with him. Digital Jimmy presses a button on a remote control, which changes Webster's outfit from a pink dress resembling her 2000 Summer Olympics opening ceremony costume, to pink crop top and pants. Webster then sings in a microphone for the first one minute of the song, starts dancing then as the song finishes she leaves the space ship and goes on another space ship ending the video. Webster stated that the back-up dancers in the video were her friends from her dance class.