My Imaginary Dinner Date With Kate & Leo

This week, headlines were made when it was announced that Kate Winslet and Leonardo DiCaprio were auctioning off a dinner date with the two of them in support of the Leonardo DiCaprio Foundation and a GoFundMe campaign set up to help a young British mother pay for her cancer treatments. The auction took place last night (July 26) in St. Tropez, with even Cal “Billy Zane” Hockley showing up to lend his support.

“Now we’re saving icebergs,” Zane captioned on an Instagram shot of the trio, yet made no mention of the person who bid the most to eat alongside Kate and Leo in New York at some point in the fall.

Likely because everybody knew that I deserved it the most.

We all know that I’m not a millionaire. We know that I have never been to St. Tropez, and the only times I’ve been to New York have been for a few days at a time and with the energy of a season one Kimmy Schmidt. But we also know that should I have had the chance to dine with Jack and Rose, it wouldn’t have been wasted. We would’ve talked about the environment, sure, but most importantly, we would’ve talked about each other. I would’ve made them laugh with tales of my youth and Titanic-obsessed years, while my honesty and vulnerability would’ve compelled both Kate and Leo to lean into our newfound friendship and share with me their most precious secrets.

“I’ve never told anybody that before,” is what Kate Winslet would say after an admission to us both that wasn’t nearly as big of a deal as she thought it was. But I wouldn’t say that; instead, I’d just look at her with an expression of understanding and sisterhood, comforting us both with my deep-seeded knowledge that we’ve been wasting the last two decades not being friends. Maybe she would wipe away one tear.

Which is when Leo would look at me in a newfound light. After stifling his attraction to me and my beautiful spirit, he would look at me longingly, proudly, and in amazement. “Who is she?” he would whisper to himself, too quiet to be heard by anybody but me, Kate, and himself. I would raise a Chicken McNugget in the air in acknowledgement.

“To making it count,” I would say, breaking the tension with my quiet confidence and comedic timing. He would laugh too hard, too loud, too intensely, desperately trying to ignore the instinct that he’d finally met The One. But Kate would know. And she would hold his hand under the table and give it a squeeze, signalling that it was okay — that he could finally just be himself.

Which is when she would slip from the table and leave us to ourselves. Leo and I, just a boy, standing in front of the love of his life, asking her for this minute in the Times Square McDonald’s, to signal the beginning of the rest of their lives.

“You saved the icebergs and you saved me,” he would say, bringing two pies for a dollar back to our booth. I smile coyly, before telling him that I’ll never let go. Because I never had. Because I had no choice but this dinner to go perfectly: I had sold my belongings and no longer had a car or place to live to ensure that I could afford this dinner. I was his Jack Dawson, finally.

“So you wanna go to a real party?” I would say.

And that’s when Leo would take my hand as I led him to Guy Fieri’s restaurant. Our new address? Flavortown.


Tags: Anne T. Donahue

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