I Went On a Date with My Celebrity Crush. Here’s What I Learned

On a random Friday afternoon in early August of 2021, I opened up my Instagram account to obtain that one particular of my beloved Los Angeles-based mostly comedian/podcast hosts/Tv set and movie stars was putting up a reside video clip from a espresso store down the street from my apartment in Denver, Colorado.

I did some investigating and found that he was in city for a comedy show, which was bought out all three nights.

On a whim I shot him a DM, specified he’d by no means see it:

“You’re in Denver and I am this sort of a enormous lover of yours! I’ve listened to just about all of your podcasts, watched your collection and, person, I sense like I just get you. In any case, it oddly warms my heart to know you are in the exact same city as me appropriate now. Acquire care, Jillian.”

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

Me on a the latest day in Colorado, exactly where I reside. Courtesy Lauren DeFilippo Jackson

When I opened the app all over again a several several hours later his response was waiting around for me:

“Thanks. The altitude is killing me.”

I responded with, “Easy on the caffeine and consume heaps of h2o.”

Him: “Ok.”

Me: “Ok to you way too.”

Without the need of offering it any imagined, I made the decision to shoot my shot in my up coming concept: “What are you accomplishing tomorrow? Let us get collectively. Never you want to have a dialogue with an individual who is not well known?”

I’d moved to Denver in 2020 immediately after 17 a long time of dwelling in New York Town. I’m a publicist by job, and through my time residing and operating in NYC, I’d attended a whole lot of market activities with big stars of all types.

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 occasion for Foodstuff Network Magazine, many years in the past. Before in my career, schmoozing with celebs was a plan aspect of my everyday living.Courtesy Jillian Sanders

As a young woman, I dreamed of the lifestyle I’d at some point have in my 20s and 30s. Attending photoshoots with celebrities, getting my name on the masthead of prestigious journals, jogging from conference to meeting in substantial heels with iced coffees.

But, in excess of time, getting all over VIPs mostly dropped its luster. Coming to comprehend that famous people are just individuals like anyone else dulled my urge to post about my encounters on Instagram or chat about how I acquired to journey in a automobile with a popular person by myself for two hrs. By the time I reached my late 30s, I longed for a drastic life-style change.

I moved to Colorado at 38 in the course of the pandemic. By yourself in a new metropolis, I sustained myself on a constant diet program of podcasts, Television set series and movies. And though I generally have an in general indifference toward fame these days, there are some celebs whom I come across to be unique — not mainly because they are in the highlight, but mainly because I have an admiration for their function or obtain that they have by themselves with a likable sincerity.

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

This took place to be the scenario with my aforementioned DM buddy. Upon going to Denver, I stumbled on his Tv sequence and binge-viewed it above the training course of two months. I liked his exhibit, and commenced listening to more of his podcasts as a consequence. As I walked the streets of my new city with his voice routinely in my head, he began to truly feel like a pal.

And now, on a whim, my well known good friend was agreeing to meet up with me for lunch.

Thankfully, my many years functioning in media had groomed me for interactions with people in higher places. Also, nearing 40, the insecurities of my youth had extensive remaining me. Youthful me would have required a week to locate the ideal outfit, a fresh new manicure/pedicure and a smooth blowout.

But with much less than 24 hours’ discover, I opted for my favorite Free Men and women skirt, a very simple white Madewell major and system Birkenstocks (so extremely Colorado). No time for a manicure and hair done by yours actually.

I pulled up to his hotel in an Uber and he was ready in the lobby in an old T-shirt and shorts. (I have red hair, so I’m rather quick to location.) He pointed at me. That you? I pointed back at him with the exact gesture. I could tell promptly that we were being excellent.

“Are you hungry? Must we try to eat? Need to we get espresso? What?” he asked in his mensch-y, amusing, eccentric voice.

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

Over iced teas and tacos he questioned about my time in New York, my family, my vocation. I requested him about his show and gave him the specifics about what I liked about it. I went to faculty for theater so speaking store about film and television is a favorite pastime of mine. His, also.

After lunch we stopped for coffee. I explained to him I’d just booked my initially excursion to Hawaii, and he told me Kauai was a person of his favourite places to stop by. “I’ll give you a guide you require to read ahead of you go,” he stated. 

Three hours passed, and we started going for walks him again to his resort. “Do you want to come to the exhibit tonight?” he asked. Of study course I mentioned sure.

I went back again to my place, showered, adjusted. I believed about how effortless the working day had been, how purely natural the dialogue flowed. I privately pat myself on the again for how considerably development I’d made. Decades ago, this would have been an event I would be texting anyone about. Now, it felt pretty much organic. Surreal, but also, regular.

Later on that evening, I was sitting down in the entrance row of his show. The viewers went berserk when he walked on stage, and he delivered as promised. After the display, we achieved up in the greenroom. 

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

On the stroll back to his hotel I again felt at simplicity, as I had the entire day. He was leaving the subsequent morning for LA to show up at a premiere the subsequent night for a massive movie he was in. There was a aspect of me that wished we could see every single other the subsequent day, and the next, and the future. But the other, smarter, more mature, wiser portion of me didn’t even start to play that activity with myself.

I enable it go.

I’ve been on a great deal of good dates, and I usually issue whether or not or not I’ll hear from the male. Where by it will go. How I acted. What it all signifies. 

But this time, I didn’t issue just about anything. We took a selfie, and I sent it to him when I obtained property. He messaged me that he genuinely appreciated expending time with me, and I considered him. At the same time, I realized that this most possible would not change into anything a lot more — and, in fact, I didn’t want it to. Maybe the aged me would, but the new me knew much better.

The following day, whilst looking at pictures of him in his tux at the motion picture premiere, surrounded by press and Oscar winners, I assumed, “Ha, I know that male!” 

Then I started seeking for a serious boyfriend.