After her service, Jorgensen began exploring the possibility of gender-reassignment surgery. She began taking the female hormone ethinyl estradiol on her own. She researched the subject with the help of Joseph Angelo, a physician who was the husband of one of Jorgensen's classmates at the Manhattan Medical and Dental Assistant School.
Sweden was the only place where doctors were performing the surgery. During a trip to Copenhagen to see relatives, however, Jorgensen met Christian Hamburger, a Danish endocrinologist and specialist in rehabilitative hormonal therapy. Jorgensen stayed in Denmark and began more advanced hormone therapy as well as the first of a series of operations.
Jorgensen was preternaturally suited to being one of the first spokespeople for her community. She was unafraid of publicity and made the most of her media fame.
Her sense of humor helped her deal with most situations, but she stood her ground whenever offended.
New York radio host Barry Gray once asked her if 1950s jokes such as "Christine Jorgensen went abroad and came back a broad" bothered her. She laughed and said it didn't bother her at all.
But another encounter demonstrated that Jorgensen could be offended by at least some queries: Jorgensen appeared on an episode of The Dick Cavett Show, during which the host asked about the status of her romantic life with her "wife," and Jorgensen walked off the show. Because she was the only scheduled guest, Cavett spent the rest of the night talking about how he had not meant to offend.
Jorgensen had a fairly successful entertainment career, recording, performing in clubs, appearing on radio and television shows, and writing books and articles. Her autobiography was eventually made into a film.
The Associated Press wrote more stories about Jorgensen in 1953 than anyone else — more than the new president Eisenhower or Marilyn Monroe. The world did not fear transgender people then as much as hold them in awe, and she was the perfect first experience for many.
Jorgensen imitated many of her favorite stars in her nightclub act: Marlene Dietrich, Talullah Bankhead, and, strangely enough, Doris Day. They all became fans and friends, along with many other entertainers of the day.
She was thwarted by legal technicalities several times when trying to be legally married to a man — a problem that continues for transgender people today. And at the end of her life she said she never regretted the surgery.