Britney Spears: The Videos

The video begins with Spears appearing bored in class at high school. Her assistant Felicia Culotta played the role of Spears's teacher. When the bell rings, Spears runs out into the hall and begins a choreographed dance in the corridor. After this, Spears is outside, now adorned in a pink athletic outfit, and seen in a car. Along with a couple of other students, she performs a number of gymnastic moves before heading back inside. She is then sitting on the bleachers in the gymnasium watching a basketball game, and she dances in the gymnasium. Her love interest is revealed sitting close to her, played by her real-life cousin Chad.

The video begins with Spears, in a long sleeveless white dress, walking barefoot through a lawn to a telescope, and looking through it. The concept was later changed to a man and a dog walking on the beach, portraying the singer as the girl next door, watching her love interest, played by model Chad Cole, from afar. The beach location was kept, and the music video intercuts with scenes of Spears' dancing on the Paradise Cove pier with her dancers dressed all in beach-friendly white attire, then Spears sits near a car. A writer of Rolling Stone noted the video is best known for "purifying the sexy persona Spears introduced in the '... Baby One More Time' video".

The video opens with Spears as a waitress of a dance club. She then goes with other waitresses to their dressing room, where they finish their makeup and change costumes. Spears, now wearing a sexy, green sequined outfit, goes through the corridor to the dance floor with her friends, and starts to perform a high-profile choreography, including a chair dance sequence referencing Janet Jackson's "Miss You Much" video, which Spears also referenced in live performances of the song on the Crazy 2k Tour. Scenes of Spears singing in front of a shining orange sign with the word "CRAZY" are also seen throughout the video. On August 24, 1999, the music video debuted at number four on Total Request Live. It is the longest running by a female artist on TRL, staying on the top ten for seventy-three days. The video was nominated on the category of Best Dance Video on the 2000 MTV Video Music Awards; it lost, however, to Jennifer Lopez's "Waiting for Tonight" (1999).

The narrative of the video shows Spears dreaming as she sleeps in her room. As the dream begins, Spears is shown in a blue and silver futuristic room with several different levels, where she sings and walks around, and puts her feet on the wall while wearing a shiny silver outfit. MTV news reporter Ellen Thompson considered it the sexiest moment of the music video. As the video continues, Spears is seen on top of the apartment building she lives in, performing a dance segment in a red top and black skirt with a few backup dancers. The following scenes shows the singer wearing white clothes and singing in the room in which she is sleeping, while her love interest comes into her room to see her. Together, they start a pillow fight that shortly ends after Spears is shown again in her room still sleeping, however, now with a smile upon her face. A longer dance segment intercalates with all the scenes during the whole video.

The music video portrays Spears packing up her belongings, as she readies herself to move away from home, and feeling upset because she knows that she is going to miss her first love. Throughout the video, scenes of the couple's past are also seen and Spears is sitting on a tire swing, including one where they climb up onto a windmill, with Spears singing the song, and Spears is standing by a billboard that reads "Welcome to Cedar Springs Gardens" similar to the video "Lucky". Before the end of the video, Spears is waiting at a bus stop while, at the same time, her first love is driving to come see her one last time. However, by the time he finally gets there, Spears had left him behind and taken the bus.