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The year 2366 saw Calloway serve as a volunteer for six months with San Francisco Emergency Medical Services. The following year, she worked an emergency medicine rotation at San Francisco's Mercy Hospital. Calloway attended Starfleet Academy, graduating in 2367 in the 94th percentile. (ST video game: Starship Creator)
Calloway became a medical technician aboard the USS Exeter. She participated in the rescue of colonists from Angkor III in the 2368, receiving a commendation for her knowledge of Klingon customs. (ST video game: Starship Creator)
By 2370, the two were romantically involved. Kwan joked that Calloway "wouldn't be able to get away with anything" around his mother, who was a telepathic Napean. The last time Calloway saw Kwan, they were planning an upcoming shore leave together. Two nights later, Kwan committed suicide, influenced by an empathic vision he experienced on the Enterprise. Calloway urged Counselor Deanna Troi to find out what happened. Deom 2370-2371, she was a supervisor of the emergency trauma team during second shift. (TNG episode: "Eye of the Beholder", ST video game: Starship Creator)
Calloway received a promotion to Lieutenant Junior Grade, based on Doctor Beverly Crusher's recommendation, in mid-2371. The same year, she coordinated medical teams in the aftermath of the Enterprise's destruction at Veridian III. (ST video game: Starship Creator)
The next year, she passed the medical board exams and earned a promotion to full Lieutenant. In mid-2372, she became a resident physician and transferred to the USS Enterprise. During the Battle of Sector 001, she served with distinction and assisted in Sickbay's evacuation. (ST video game: Starship Creator)
- Starship Creator has a contradiction - the software's summary section states that the last ship she served on was the Enterprise-D, but her biography discusses her time serving aboard the Enterprise-E.
- Ensign Calloway was portrayed by Johanna McCloy.
In an empathic vision experienced by Deanna Troi, Calloway became romantically involved with Worf. Troi, jealous of Calloway, tried to kill her, but accidentally shot Worf instead. (TNG episode: "Eye of the Beholder")