Ensign Maddy Calloway was a member of Starfleet and served aboard the USS Enterprise-D as a medical technician in 2370. She had been romantically involved with Lieutenant junior grade Daniel Kwan for a few months as of the time of his suicide, having known him for over two years. Their relationship had progressed slowly. She recalled loving that he could look at her and know what she was feeling.

When questioned during the investigation into his death, she stated that she could think of no reason why he would kill himself. She also said that they had no problems romantically, and he was a very upbeat person. They had even planned a shore leave together. (TNG: "Eye of the Beholder")

Maddy Calloway was played by actress Johanna McCloy.
According to the video game Star Trek: Starship Creator, Calloway was born on Meezan IV to parents Colleen and Thomas Calloway. She had a sister named Danielle.

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