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Gladu experienced being treated differently from a very young age due to her feminine behavior and appearance. Gladu's mother, Rosemary, stated in a YouTube video that Gabrielle had asked her about gender identity and why she was a boy instead of a girl. Gladu stated in an article for the Huffington Post that she "used to wear my mom’s dresses and makeup, and it wasn't easy in the beginning since I wasn't transitioning".

In March, 2019, Gladu sparked public attention after getting into an online feud with singer/songwriter Azaelia Banks on social media website Twitter. The argument was led by personal and public messages from Gladu and Banks, discussing the role of transgender and cis-women in society. Banks based her argument on the premise that biological women are being erased by transgender persons, to which Gladu rebuked. Following the argument, Gladu's account Send2Gabby was suspended, while Banks' deactivated. After the feud, Out Magazine published an article titled "Azealia Banks isn't a Queer Ally-- She is a Bully!", where screenshots of the argument were posted for public view.

Since undergoing sex reassignment surgery in 2017, Gladu has left YouTube, and focused more on personal endeavours including becoming more involved with the twitter community instead of YouTube. Gladu has stated that she has no desire to return to YouTube and would much rather spend her time "smoking pot and making music"

Gabrielle co-founded a Go-Fund Me with Amina Lakin, called Into Full Bloom in September 2016. The initial success of the company push started the organization called Into Full Bloom, Inc. Within the first 6 months, the company had raised $2,450 in donations, 70% of which came from a single donor. In the 6 months following, the organization raised $25,000. Gladu and Lakin founded the organization together, and they aimed to help transgender people by supplying them with resources and things that would help them transition easier if it's not possible to do on their own. Into Full Bloom, Inc stopped being active at the beginning of 2017 due to Gladu's ongoing battle with mental health that required her to receive medical treatments.

In 2016, Gladu released multiple demos of music that were from past projects including her scrapped album The Meeting of Minds. The following year, Gladu then teased a mixtape full of music inspired by the 1980s synth pop, and the 90's Riot Grrrl movement. That project was also scrapped due to creative difference with her producers.

Gladu has been involved in helping the trans community gain recognition and visibility, as well as dedicating much of herself to documenting her transition online. Gladu has worked with The Advocate, and was named one of the 25 Trans Pioneers of 2015.

Gabrielle started to medically transition in April 2014, by taking Lupron to block the production of testosterone. Gabrielle then started taking estrogen as part of HRT on March 24, 2015. Gladu has been referred by her team at CHEO to surgeon Dr. Brassard to perform her SRS. Gladu received her surgery on August 23, 2017, in Montreal, Quebec.

On September 27, 2015, Gladu received the message that her name had been legally changed to Gabrielle Diana Gladu. Gladu uploaded a video to her Twitter, which was filmed by her cousin. Gabrielle's mother surprised her with a cake that revealed that her name was legally changed. Gabrielle revealed that her forename Gabrielle was inspired by Coco Chanel, and her middle name, Diana, was a tribute to Diana, Princess of Wales, whom Gladu became influenced and inspired by.

Gabrielle started her first year of high school at a different school board system, and intended on starting the year identifying as male. Gladu has said that she didn't begin school, already transitioning, because she wanted to see how people would react to her as a gay boy. Gladu began changing her pronouns at school, and first asked her classmates and teachers to call her Bebe. Already living as a female at school and with her family, Gladu decided to publicly come out as transgender in December 2013. Gabrielle began to see Dr. Stephen Feder, and Dr. Margaret Lawson at the Diversity Clinic, at CHEO.

Gabrielle attempted suicide on December 12, 2012. Though Gladu was not yet out as trans, the suicide attempt was related to her gender identity and confusion surrounding her female identity that she had yet to explore. In regards to her suicide attempt, Gladu said, "I was very, very confused. I knew something was different about me. I was so afraid of what people would think of me.". Following her suicide attempt, Gabrielle began treatment at CHEO, and began intensive therapy by seeing social worker Richard Voss to help her develop coping mechanisms and address the issue. During the time she saw Voss, Gladu began to discover that her female identity was becoming stronger, and she started to research Transgender people and educate herself on Gender identity. Gabrielle has stated that she came out to herself on August 3, 2013, and had recorded a YouTube video coming out as Trans, but never ended up posting it due to fear of rejection and hatred.