Jenny Shimizu recalls dating Madonna in revealing documentary series

Jenny Shimizu, a model and actress, reflected on her relationship with Madonna during the 1990s in a new documentary series. She described feeling like a 'high-class hooker' due to the nature of their encounters, which often involved spontaneous trips to meet Madonna at her shows. Shimizu recounted how she would finish work for Prada, catch a flight to Paris, and return to Milan after their brief meetings. This lifestyle highlighted the power dynamics in their relationship, with Shimizu feeling unable to say 'no' to the iconic singer. In addition to her experiences with Madonna, Shimizu has been an advocate for LGBT+ rights, participating in demonstrations for marriage equality. Her journey in the fashion industry began when she was discovered while working as an auto mechanic in Los Angeles. Shimizu expressed gratitude for her visibility in the 1990s, particularly when she appeared on billboards in Times Square, which was a significant moment for her as a Japanese-American and a member of the LGBTQ+ community. Shimizu also had a notable relationship with Angelina Jolie, whom she met on the set of the film Foxfire. Jolie described her feelings for Shimizu as love at first sight, indicating the depth of their connection. This period was pivotal for both women as they navigated their identities and relationships. Overall, Shimizu's reflections provide insight into her personal experiences and the broader cultural context of the time, illustrating the challenges and triumphs faced by individuals in the LGBTQ+ community during the 1990s.