Desmond's photograph was a photograph featuring him and his girlfriend Penny at a Marina. The picture was taken the day they broke up, and Desmond had his copy when he entered the sailing race that eventually landed him on the Island. He held on to the photograph for the three years he lived in the Swan as a way of remembering Penny. Penny kept her copy on her night table. ("Orientation") ("Live Together, Die Alone")
Transported back to 2004 after having travelled to 1996, Desmond found the photograph at the remains of the exploded Swan. He regretted having broken up with Penny, and wished to return back to act differently if he were granted a second chance. Desmond saw the photograph again later, when Claire approached and said that Penny was beautiful. ("Flashes Before Your Eyes")
Penny's copy was somehow acquired by Naomi Dorrit before her arrival on the Island, most likely through her employer Charles Widmore, and was used by her as a way to explain her arrival on the Island, lying that she was hired by Penelope. ("The Brig") ("Through the Looking Glass")
- The producers suggested that the origin of the photograph might be different in Desmond's two timelines. They further suggested this might explain the disparity in the apparent number of copies of the photograph that should exist. (Official Lost Podcast/February 20, 2007)
- The real-life backdrop to the photograph is the Ala Wai Yacht Harbor in Honolulu.
- The actress that appeared in the photograph from the original airing of "Orientation" was obviously not actress Sonya Walger, who played Penelope for the rest of the series. In the rerun airing of "Orientation" on 6/14/06 (and on the DVDs), this continuity error was corrected by replacing the original photo with the one from the finale (showing Sonya Walger). Some fans say that the woman in the original photograph resembles Lisa Fraser, who played Arlene Stewart.
- Desmond's photograph when being taken in "Flashes Before Your Eyes" was very different from the one used before and since. Here he was wearing a different shirt, orange in color compared to the bright red on the original. The original covered his neck while here his neck was bare. The background of the marina was different as were Penny's position and facial expression.
- For fan theories about these unanswered questions, see: Desmond's photograph/Theories
- How did Naomi get a copy of the photograph and why was she carrying it?