Philly Files #1

Before we left for Philadelphia, Michael insisted there was one thing I needed to do.

I needed to watch Rocky.

Apparently, showing up in Philadelphia without having seen Rocky is like being invited to Thanksgiving dinner and not knowing what a turkey is. Could you still participate? Technically. Would everyone quietly judge you? Absolutely.

So a few nights before our trip, we grabbed our Halo Top, jumped in bed, and watched Rocky.

Now, I knew the basics. I knew there was boxing. I knew Sylvester Stallone spent a lot of time running around Philadelphia in gray sweatpants, but who knew there was a whole culture of running up and down some steps? 

But what I didn’t expect was Adrian.

While Michael was excited for me to understand Rocky, I became completely invested in Adrian.

The shy pet shop girl, the awkward conversations, the quiet moments, their love story.

There was something about Rocky and Adrian that felt so genuine. Neither of them was glamorous. Neither of them was perfect. Their relationship wasn’t built on grand gestures or dramatic speeches. It was built on companionship, comfort, and the small, genuine moments. The kind of love that grows slowly, the kind that feels familiar.

As I sat there watching, I found myself thinking about Michael and I. Not because Michael is running through Philadelphia at sunrise, preparing for a heavyweight title fight. Although after spending a few days in Philadelphia, I can confirm he gets just as excited about Rocky as Rocky ever got about boxing, because what I loved about their relationship was exactly what I love most about ours. 

The little things, our coffee runs, long drives, Inside jokes, long conversations that begin somewhere and somehow end somewhere entirely different. The feeling that even ordinary moments become memorable simply because you’re experiencing them together.

By the time the movie ended, I wasn’t just excited to visit Philadelphia. I felt connected to it somehow, like I had already been introduced to a small piece of its heart.

From that point forward, Michael fully committed himself to becoming my unofficial Philadelphia tour guide.

And when I say committed, I mean committed.

I received a complete Philadelphia educational symposium and a Google Doc before ever stepping foot in the city.

Neighborhoods, sports, history, cheesesteaks, the Eagles, the Flyers, baseball, passion, loyalty, complete insanity.

And perhaps most importantly, the concept of a jawn. To this day, I still don’t fully understand what a jawn is. I’ve had it explained to me dozens of times. I nod every time. I pretend I understand every time. And then someone uses it in a sentence, and I realize I’ve learned absolutely nothing. Am I jawn? Is that beer a jawn? Are we all jawns? At this point, I’ve simply accepted that everything in Philadelphia is a jawn until proven otherwise.

By the time our flight took off, I felt strangely prepared, like I’d spent the previous month studying for an exam on Philadelphia culture.

I knew Rocky, I knew Adrian, I knew cheesesteaks were serious business, And I almost knew what a jawn was.

Almost.

The excitement hit somewhere above the clouds. That familiar feeling that always arrives at the beginning of a trip. The kind that makes airport coffee taste better than it should. The kind that makes every boarding announcement sound like the beginning of an adventure.

My hands were shaking as we descended. I remember looking out the airplane window as Philadelphia slowly appeared beneath us.

Rows of brick homes, church steeples, the winding river. The city looked old, not old in a tired way, but in a beautiful way — like a city carrying stories.

What I didn’t know then was that Philadelphia wasn’t just going to become another city I’d visited. It was going to become one of my favorite memories. And most of that had nothing to do with Philadelphia itself. It had everything to do with seeing it through Michael’s eyes. Michael had booked everything. The flights, the hotel, the plans.

We checked into The Bellevue. To celebrate our anniversary, they upgraded us to a suite complete with champagne and fresh fruit.

Nothing makes you feel wealthier than complimentary fruit. For approximately twenty minutes, reality lost custody of me. The city stretched out beneath our windows, historic rooftops. The kind of architecture that instantly makes Florida feel like the new kid on the block. 

After dropping our bags with the concierge, we headed upstairs to the rooftop for coffee before exploring.

The air was crisp, and the skyline sat beneath a blanket of gray clouds.

And as we sipped our coffee, Michael struck up a conversation with another man wearing Flyers gear. Philadelphia sports fans seem to have a unique ability to identify one another from remarkable distances. It’s almost supernatural. The two of them talked hockey while I sat there contributing absolutely nothing useful to the conversation.

About thirty minutes later, the gentleman left. The bartender walked over and casually informed us we’d just spent the better part of an hour talking to a former mayor of Philadelphia. Naturally, we had absolutely no idea.

Our first stop was the Philadelphia Zoo. The first zoo ever built in the United States. As we wandered through exhibits and watched animals roam overhead, I found myself paying less attention to the animals and more attention to Michael.

The tigers were incredible, don’t get me wrong, but there was something special about watching someone show you a place they love. Every few minutes, another story appeared. A memory, a recommendation, a piece of childhood, a piece of home.

I loved that our first memory in Philadelphia wasn’t some extravagant attraction. It was simply walking around a zoo together.

Talking, laughing, watching tigers, and seeing little pieces of Rocky come to life. Including the place where Rocky proposed to Adrian, in which Michael reenacted with an impression that was unfortunately much better than it had any right to be.

That afternoon, we wandered through Fairmount Park toward Boathouse Row.

The river reflected the cloudy sky, crew teams rowed through the water in perfect rhythm, runners passed us bundled in sweatshirts, and everything felt cinematic. The boathouses stood proudly along the shoreline, each one looking like it belonged inside a storybook.

At one point, we grabbed ice cream from a Mister Softee truck. A decision that made absolutely no sense, considering how cold it was, and yet somehow ice cream always tastes better when you’re slightly uncomfortable. Michael stood there in his 1997 Lindros Stanley Cup Flyers jersey, holding a cone while I tried unsuccessfully not to get ice cream on my jacket. 

Eventually, we reached the Philadelphia Museum of Art.

The Rocky Steps.

The moment had finally arrived. Of course, I had to run them. Did I sprint triumphantly to the top?

No.

I made it dramatically and slightly out of breath. Michael made it look significantly easier. But standing there overlooking the city, I finally understood something. Philadelphia wasn’t just a city to Michael. It was a time capsule. Every street seemed attached to a memory. Every neighborhood carried a story. 

Watching him walk through Philadelphia felt like watching someone ride a bicycle they hadn’t touched in years. The muscle memory was still there. The nostalgia came flooding back effortlessly, and somehow, I got invited into all of it. That might’ve been my favorite part of the trip. Not seeing Philadelphia, but experiencing it through Michael's eyes.

By evening, we were freezing. Exhausted. Dangerously hungry. The kind of hungry where suddenly everything around you becomes irritating. So Michael brought us to Chicha San Chen.

The tea, the boba, the warmth, the incredible Teaspresso machine!

Everything felt perfect. For a little while, we sat there watching the rain outside while our hands thawed out. Then we bundled ourselves back into coats and headed back out.

Umbrella overhead, cold wind, wet shoes, numb fingers, and a mission.

My first Del Rossi cheesesteak…

The anticipation had been building for months. Michael had talked about Philadelphia cheesesteaks throughout our entire relationship. At this point, I felt like I knew them personally.

Standing there soaked from the rain and absolutely starving, taking that first bite felt less like eating dinner and more like participating in a religious experience.

Was it the best cheesesteak in Philadelphia?

I have absolutely no idea.

Could I make it better at home? 

Mmm probably. 

I was cold, exhausted, and one skipped meal away from a complete personality change, but somehow everything aligned perfectly.

The rain, the city lights, the cold, Michael’s excitement. The feeling of finally experiencing something he’d spent months talking about and it coming to life. That cheesesteak will always taste like Philadelphia.

After dinner, we wandered through Chinatown in the pouring rain.

Neon signs reflected in puddles, lanterns glowed overhead, steam drifted from restaurant doorways, the whole neighborhood felt dreamlike. Like we’d accidentally stepped into another world.

We stopped into a small bakery and bought egg tarts and a matcha Swiss roll, then grabbed a mango dessert from another shop, and somehow found ourselves inside a hidden basement esports center playing League of Legends.

Which honestly summarizes our relationship perfectly. One minute we’re having a romantic evening in Chinatown. Next, we’re in a basement playing video games.

Completely unplanned, completely random, and yet one of my favorite memories. Because the best moments are rarely the ones you schedule, they’re the ones you stumble into.

By the time we made it back to the hotel that night, exhausted and soaked, Philadelphia already felt different. Less like somewhere I was visiting, more like somewhere I was beginning to know.

And then Philadelphia kept unfolding.

The next morning, we woke up sore in the way only travel can make you sore, pleasantly worn down from a day spent actually living. The city hummed outside our window while we slowly got ready and headed toward Reading Terminal Market.

The moment we walked through the doors, every smell imaginable hit us at once.

The fresh bread, roasted coffee beans, sweet donuts, roasting meats, chocolate, spices!

If heaven has a food court, I’m fairly certain it looks exactly like Reading Terminal.

We grabbed coffee sweetened with homemade blackberry syrup and stood there watching warm donuts being made right in front of us. They came out golden, steaming gently in the cool morning air, each one seeming to last only a few seconds before being claimed by an eager customer. We ate ours while they were still warm enough to fog the paper bag. Soft, pillowy, and impossibly fresh, they tasted like the kind of thing you're always hoping for when you order a donut but seldom get. The sort of food that silences conversation for a moment because everyone's attention is exactly where it should be.

As we wandered through the market, it became increasingly difficult to maintain any sense of direction. Every aisle offered a new distraction. Fresh pastries, flowers, local honey.

At least three separate times, I looked up and realized Michael was no longer beside me.

Not because he had wandered off…

Because I had.

Every time something caught my eye, I'd wander off with the confidence of someone who had absolutely no plan for finding their way back. Being a chef in Reading Terminal is dangerous. You leave with equal parts admiration and professional jealousy. 

Naturally, we then had to grab our third coffee of the day.

We wandered over to Drip Café, which felt less like a stop and more like an acknowledgment that we had fully surrendered to caffeine for the day to keep us going.

Afterwards, we walked around some shops where I found a personalized journal for my sister’s twenty-first birthday and a Flyers journal for Michael to commemorate our first Philly Trip together.

Eventually, we made our way toward Elfreth’s Alley. The oldest continuously inhabited residential street in the United States. Cobblestones stretched beneath our feet while narrow, colonial-style homes lined either side of the street. Flower boxes spilled from windows. Flags moved lightly in the breeze. Everything felt paused, but not staged.

I stood there for a moment, thinking about how many completely ordinary days had taken place in a space like this. Not the dramatic, headline moments –  just people coming and going, meals being made, windows being opened, life happening quietly in the background. It’s the part of history that’s always stayed with me: how every “historic place” was once just somewhere someone lived their normal life. Later that day we visited the Liberty Bell to see the famous crack, the crowds, and the history.

And while I appreciated all of it, one of my favorite moments happened shortly afterward inside a beautiful Orthodox church. The moment we stepped through the doors, the city disappeared. The smell of incense lingered in the air. Candles flickered softly. Golden icons glowed beneath the dim light, and rays of sunshine pierced through the stained glass windows. Everything felt still, sacred, timeless.

We ended up having a conversation with the priest that neither of us expected. One of those conversations that somehow stays with you long after it ends.

Travel gives you gifts like that. Moments you never planned for. Moments that quietly become some of the most meaningful parts of a trip.

Later, we found ourselves inside McGillin’s — one of the oldest pubs in Philadelphia! The sticky floors creaked beneath our feet. The walls seemed to carry generations of stories. And there we were adding our own small chapter. By this point, I had accumulated enough Philadelphia gear that I was beginning to feel like a local. Or at least that’s what I told myself 9the locals may have disagreed).

That evening, Michael surprised me with dinner at the Victor Cafe, made famous through Rocky’s movies. As we sat together eating dinner, I found myself thinking back to Rocky and Adrian, to the simplicity of their relationship, to the way love often lives inside ordinary moments.

Years from now, I probably won’t remember what I ordered. But I’ll remember him sitting across from me. I’ll remember the conversation. I’ll remember how content I felt.

And then, because life enjoys keeping things interesting, we followed our romantic serenaded opera dinner with a Born of Osiris concert.

One minute, we were having a quiet dinner. The next minute, I was standing in the front row watching my first mosh pit.

After all, relationships are all about balance, right? 

The people at those concerts fascinated me. Covered in tattoos, heads banging, screaming lyrics or what I thought were words, launching themselves into complete chaos. And yet somehow everyone was incredibly nice.

I watched people crash into each other like human pinballs, only to immediately help each other back up. One minute I was front row standing with Michael by my side, the next I noticed him sprinting to the back and being thrown in the air crowd surfing to the stage.  

Everything was loud, violent, slightly terrifying, and yet wholesome. Not a combination I expected. But somehow it worked.

The next morning, we ordered room service and stayed in bed longer than we should have.

No alarm, no schedule. Just coffee and breakfast under warm blankets. Some of my favorite moments from trips are the slow ones. The pauses between adventures. The chance to simply exist together. Eventually, we wandered through the city again. The weather was perfect. Spring flowers were in full bloom. The parks were crowded. The city felt completely different from how it had in the rain.

Of course, we had to make a pit stop at Rolex. What better way to mark our first trip together than with a timeless piece — something that will always remind us of this special chapter and the memories we made along the way

We then found a café where we had lunch outside, drinking and people-watching.

Afterward, we explored the Philadelphia Museum of Art before driving to Lambertville. And if Philadelphia felt historic, Lambertville felt like something out of a movie.

The little shops, the river, the charm, the quiet.

That evening I met Michael’s grandfather. Someone he is incredibly close with. Watching them together was special. You learn a lot about a person by seeing where they come from. By seeing who helped shape them.

After dinner, we walked across the bridge beneath a full moon. The lights reflected across the water, the evening air was cool, and everything felt still.

For a few moments, the entire world seemed to slow down. Those are the moments I wish I could bottle.

The next morning, we packed our bags (something I always hate doing). Trips are strange. You spend weeks looking forward to them. Then suddenly you’re folding clothes and realizing it’s almost over.

Before heading to the airport, we wandered through a local farmers’ market. The air was cold while we sipped hot apple cider and ate fresh apple donuts, taking the last of our time soaking up the nostalgia of Philly (realizing Philly was already starting to feel like a memory before we even left).

Nobody was rushing. Nobody wanted the trip to end.

Eventually, we made our way to the airport.

And because apparently we hadn’t made enough memories yet, we proceeded to get completely hammered in the lounge.

A fitting finale

When I think about Philadelphia now, I don’t think about the landmarks first.

I don’t think about the Liberty Bell, or the Rocky Steps, or the cheesesteaks. I think about Michael. I think about watching him walk through a city that feels like a time capsule. I think about the stories attached to every corner. The memories hidden in ordinary places. The nostalgia that followed him through every neighborhood we visited.

Philadelphia showed me where he came from. But more importantly, it showed me pieces of who he is.

And somewhere between Rocky and Adrian, rainy nights in Chinatown, cheesesteaks, church conversations, old pubs, metal concerts, zoo tigers, moonlit bridges, and airport lounge cocktails, Philadelphia became more than a city to me, too.

It became a collection of moments. The kind you’ll tell your family about years from now. The kind you’ll revisit in your mind when life feels busy. The kind that reminds you how beautiful ordinary days can be.

And the funniest part?

We barely scratched the surface.

Because somehow, before this story was even finished, we were already on our second flight out to Philly for our next trip.

Which feels fitting.

After all, Rocky got a sequel.

And so did we.