From the minute she writhed around in a gondola in Venice, Madonna has been my number one pop icon. I was a teen when her career exploded in 1984 with Like A Virgin (and that iconic Venetian video). Her lyrics, sexuality and fashion sense were both shocking and influential. She was gutsy, outspoken, sexy and provocative. For a kid who loved The Bay City Rollers and the Go Go’s, Madonna was next level fabulous. I walked to fashion school in Los Angeles with my blonde permed hair knotted up in a pink tulle bow and my leggings topped with a low-slung “Boy Toy” belt. (What I wouldn’t give to see some photos!) I became a super fan and snapped up every album and magazine she was featured in. Years later in 2011, when I was given the opportunity to meet her in Toronto, I was terrified. What if she didn’t measure up? What if she ignored me? Perhaps I was better to admire her from afar? 

At the Toronto International Film Festival in 2011. Photo by George Pimentel. Courtesy of The Hudsons Bay Co

Rumours swirled around the Toronto International Film Festival that Madonna would be in town to premiere her film W.E. (about the scandalous romance of Wallis Simpson and King Edward VIII). I received a cryptic call from my friend Geri at The Bay to save the date for one of TIFF’s busiest nights. I was already double booked so declined. She called me and said one word – Madonna. I cancelled my plans and freaked out.

Madonna teamed up with The Bay to sponsor the screening and after-party since they were launching her Material Girl fashion collection and first fragrance in Canada. A handful of guests (Richard Baker and his wife who own HBC, key editors, Suzanne Rogers) were invited to meet her before the screening, and then attend a private dinner. When the petite pop star entered the room, I could barely see her but all of the energy flowed towards her. I squeaked out a hello when George Pimentel snapped my photo with her in a private room at Roy Thompson Hall. Even George was impressed with her (he’s met everyone) and we quickly did whatever he told us. Dressed in Dolce and Gabbana, Madonna was all business: take a photo, say hello, move on. Everyone in the room was skating on eggshells around her. I can only imagine how nervous she must have been about the screening. I loved the film, but not surprisingly critics savaged it. Reviews suggested she stick to pop music which I thought was infuriating. She’s an artist, period. Why can’t she try something different? I’m a picky film lover and I thought her attention to detail was superb. After the gala presentation, we headed to an intimate club just up the street for dinner. Paparazzi was swarming. One tried to grab my clutch in hopes of finding out the address I was headed to.

A small group sat for dinner, including Madonna’s film agent, hair stylist Garren, the film’s stars, and HBC executives. Eyes rolling, Madonna ignored the gushing well-wishers. The Bay’s President, Bonnie Brooks, thrust me into a seat right across from Madonna so I grabbed my chance. I choked back my growing fan girl hysteria and started to quiz her about the film’s details – the training of the pugs (a naughty breed that I know well), the Cartier jewels, the fashion, and her new star Andrea Riseborough who played Wallis. She locked eyes with me and we talked throughout dinner. We discussed her children, the fashion industry, her new fragrance, possible film subjects, and our childhoods – it was like catching up with a high school best friend. When she finally left, I was exhausted, elated and giddy – one of the best nights of my life.

Meeting someone that you admire so much for so long can be disappointing … but, lucky for me, Madonna was everything and more that I hoped for. The passion, independence and drive that had inspired me throughout my 20s was on full display that night. I feel sad for her that a film, Blonde Ambition, about the launch of her career in the 1980s, is being planned without her permission. As she has posted this week on social media, it’s her story to tell. I hope she gets that opportunity. After being savagely criticized for absolutely everything she does – from her family and love life to her musical and film directing abilities, she has earned the right to tell her own story. And I’ll be first in line at the film premiere.