Sometimes was shot at Paradise Cove in Malibu, California, and features Spears watching her love interest from afar, who is played by model Chad Cole. As he plays with his dog on the sand, Spears is seen on a lookout, by the pier and on a picnic blanket wishing she was there with him. The video also includes dance scenes with Spears and several others on the pier adorned in white. Blink-182 parodied the video in their "All the Small Things" video.
There are two edits of the video. One features mainly beauty shots during the first verse, the second edit features more dancing footage from on the pier. The radio edit of the song was used for the video, it shortens the intro and removes an instrumental bridge towards the end of the song