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I went on a date with my celebrity crush. Here’s what I learned

On a whim, I slid into his DMs — but I never thought that he would respond, or that the experience would teach me something about myself. 

On a random Friday afternoon in early August of 2021, I opened up my Instagram account to find that one of my favorite Los Angeles-based comedian/podcast hosts/TV and film stars was posting a live video from a coffee shop down the street from my apartment in Denver, Colorado.

I did some investigating and discovered that he was in town for a comedy show, which was sold out all three nights.

On a whim I shot him a DM, certain he’d never see it:

“You’re in Denver and I am such a huge fan of yours! I’ve listened to almost all of your podcasts, watched your series and, man, I feel like I just get you. Anyway, it oddly warms my heart to know you’re in the same city as me right now. Take care, Jillian.”

I closed out of Instagram and went back to my magazine.

Me on a recent day in Colorado, where I live.
Me on a recent day in Colorado, where I live. Courtesy Lauren DeFilippo Jackson

When I opened the app again a few hours later his response was waiting for me:

“Thanks. The altitude is killing me.”

I responded with, “Easy on the caffeine and drink lots of water.”

Him: “Ok.”

Me: “Ok to you too.”

Without giving it any thought, I decided to shoot my shot in my next message: “What are you doing tomorrow? Let’s get together. Don’t you want to have a conversation with someone who isn’t famous?”

I’d moved to Denver in 2020 after 17 years of living in New York City. I’m a publicist by profession, and during my time living and working in NYC, I’d attended a lot of industry events with big stars of all sorts.

With Martha Stewart at an event for Food Network Magazine, years ago. Earlier in my career, schmoozing with celebrities was a routine part of my life.
With Martha Stewart at an event for Food Network Magazine, years ago. Earlier in my career, schmoozing with celebrities was a routine part of my life.Courtesy Jillian Sanders

As a young girl, I dreamed of the life I’d eventually have in my 20s and 30s. Attending photoshoots with celebrities, having my name on the masthead of prestigious magazines, running from meeting to meeting in high heels with iced coffees.

But, over time, being around VIPs mostly lost its luster. Coming to understand that celebrities are just people like everyone else dulled my urge to post about my experiences on Instagram or talk about how I got to ride in a car with a famous person by myself for two hours. By the time I reached my late 30s, I longed for a drastic lifestyle shift.

I moved to Colorado at 38 during the pandemic. Alone in a new city, I sustained myself on a steady diet of podcasts, TV series and films. And while I mostly have an overall indifference toward fame these days, there are some celebs whom I find to be special — not because they are in the spotlight, but because I have an admiration for their work or find that they carry themselves with a likable sincerity.

I'm all smiles with Ree Drummond at an event for The Pioneer Woman Magazine.
I'm all smiles with Ree Drummond at an event for The Pioneer Woman Magazine.Courtesy Jillian Sanders

This happened to be the case with my aforementioned DM buddy. Upon moving to Denver, I stumbled upon his TV series and binge-watched it over the course of two weeks. I loved his show, and started listening to more of his podcasts as a result. As I walked the streets of my new city with his voice regularly in my head, he began to feel like a friend.

And now, on a whim, my famous friend was agreeing to meet me for lunch.

Luckily, my many years working in media had groomed me for interactions with people in high places. Also, nearing 40, the insecurities of my youth had long left me. Younger me would have needed a week to find the perfect outfit, a fresh manicure/pedicure and a sleek blowout.

But with less than 24 hours’ notice, I opted for my favorite Free People skirt, a simple white Madewell top and platform Birkenstocks (so very Colorado). No time for a manicure and hair done by yours truly.

I pulled up to his hotel in an Uber and he was waiting in the lobby in an old T-shirt and shorts. (I have red hair, so I’m pretty easy to spot.) He pointed at me. That you? I pointed back at him with the same gesture. I could tell immediately that we were good.

“Are you hungry? Should we eat? Should we get coffee? What?” he asked in his mensch-y, funny, eccentric voice.

“Yeah we can eat,” I said. “I like to eat.” I pointed to a Mexican place. “Let’s go this way.”

Over iced teas and tacos he asked about my time in New York, my family, my career. I asked him about his show and gave him the specifics about what I liked about it. I went to school for theater so talking shop about film and television is a favorite pastime of mine. His, too.

After lunch we stopped for coffee. I told him I’d just booked my first trip to Hawaii, and he told me Kauai was one of his favorite places to visit. “I’ll give you a book you need to read before you go,” he said. 

Three hours passed, and we started walking him back to his hotel. “Do you want to come to the show tonight?” he asked. Of course I said yes.

I went back to my place, showered, changed. I thought about how easy the day had been, how natural the conversation flowed. I privately pat myself on the back for how much progress I’d made. Years ago, this would have been an event I would be texting everyone about. Now, it felt almost natural. Surreal, but also, normal.

Later that evening, I was sitting in the front row of his show. The audience went berserk when he walked on stage, and he delivered as promised. After the show, we met up in the greenroom. 

“C’mon, I gotta get outta here,” he said.

On the walk back to his hotel I again felt at ease, as I had the entire day. He was leaving the next morning for LA to attend a premiere the following evening for a big film he was in. There was a part of me that wished we could see each other the next day, and the next, and the next. But the other, smarter, more mature, wiser part of me didn’t even begin to play that game with myself.

I let it go.

I’ve been on a lot of good dates, and I always question whether or not I’ll hear from the guy. Where it will go. How I acted. What it all means. 

But this time, I didn’t question anything. We took a selfie, and I sent it to him when I got home. He messaged me that he really enjoyed spending time with me, and I believed him. At the same time, I knew that this most likely wouldn’t turn into anything more — and, in fact, I didn’t want it to. Maybe the old me would, but the new me knew better.

The next day, while looking at pictures of him in his tux at the movie premiere, surrounded by press and Oscar winners, I thought, “Ha, I know that guy!” 

Then I started looking for a real boyfriend.