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The Odd Couple Project: Kylie & Casondra

Updated: Mar 31, 2023

The Odd Couple project is a study on how our differences can make stronger partnerships. These couples create a life together that honors their unique experiences and pushes back at a societal belief of a standard relationship structure.

Kylie & Casondra followed the path of many couples before them. They met in high school, dated for four years, got married, and lived happily ever after... The end. We love a happy ending, don’t we? However, without the complexities and twists of life, it would lack intrigue and adventure. I believe Kylie and Casondra are still building their happy ever after, but their story started out as Kyle and Casondra.

Kylie & Casondra © Kaylinn Gilstrap

Kylie knew something was not quite right since age six but she tried to live the way society expected Kyle to. She lived that way a long time but when you feel your body doesn't match who you are a weight settles on your shoulders. She was happy in her marriage and work was going well but she was depressed and angry. Angry that she had allowed herself to follow a path for so long that would never lead to her own peace and happiness. Eventually, Kylie not only became tired of hiding from Casondra but also denying who she truly was. So on a lunch break from work in December 2014, a week into therapy, Kylie told Casondra she was transgender and that she still loved her and would like to remain married. Then they went back to work.

Casondra had known her partner was struggling and had even contemplated if being transgender was the cause. So she was somewhat prepared but the revelation left her questioning what that meant for her. She had gotten used to the routine of their life together and this required her to rethink what box she fit into. Casondra went looking for help but there weren’t many couples like them that were sharing their experience. She eventually found the term pansexual which she describes as “Loving the soul, not the package.” And started considering how she would live her life if she wasn’t concerned about what other people thought.

It seems like change happens on a dime when you’re in it but looking back you can pick up small events that set everything in motion. Kylie and Casondra remember the steps that brought them together and they remember the steps that helped them transition. Just like Kylie, for Casondra it wasn’t really a question whether they should stay together. Two days after the lunch conversation they went shopping for Kylie’s wardrobe and slowly started making their way down a new path. Their marriage transitioned alongside Kylie.

One of the beauties of companionship is some things change and other things never do. That lunch time conversation sparked change for each of these women and in turn strengthened their union. Casondra discovered that she truly loved this person for who she was, not the physical form or the name attached. Kylie found acceptance and the joy of living as her true self. Their vows had been tested but they stood by them because why would you leave your soulmate?

Kylie and Casondra renewed their vows in September 2016 as wife and wife.

I met Kylie and Casondra while covering a panel for CNN called "Demystifying Transition - Living as Transgender in America" and later asked them to sit for my Odd Couples project.

You can hear more directly from Kylie on her podcast, Positively Trans.

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