THIRTY-THREE
Lena and I set off for a day of exploring Santorini.
I chose a stunning turquoise dress with a plunging neckline and no back.
The chiffon-like material was light and breezy, perfect for the hot sunny day.
It was revealing and somewhat transparent, but when in Europe, do as you please.
Lena wore a bright maxi that hugged her curves in the right places and flowed in the others, drawing attention everywhere we went.
Lena’s energy was contagious as always.
She flirted shamelessly with every handsome man we passed, exchanging playful glances and witty banter.
I was less interested in making connections but couldn’t help but admire her effortless charm.
We stopped at Café Oia for coffee, the rich aroma of freshly brewed espresso mingling with the salty sea breeze.
After coffee, our first stop was the iconic Three Bells of Fira.
The white church with its striking blue dome and bell tower stood proudly against the azure sky, offering a perfect photo op.
We took turns snapping pictures of each other, laughing at our attempts to capture the beauty of the place.
The air was filled with the scent of blooming flowers and the salty breeze from the sea.
Next, we wandered through the charming village of Oia, famous for its stunning sunsets.
The narrow, cobbled streets were lined with quaint shops selling handmade jewelry, local art, and beautiful ceramics.
We browsed through them, chatting with friendly shop owners who offered us samples of local delicacies like baklava and loukoumades.
By noon, the heat was starting to pick up, and we made our way to Ammoudi Fish Tavern, a small, cozy restaurant tucked by the water down a series of stairs.
We couldn’t resist the call of fresh seafood.
The fish was charred to perfection, and the shrimp saganaki was rich, cheesy, and perfectly tangy with the touch of tomato.
We sipped on Assyrtiko, the famous local white wine, while the waves lapped gently at the shore.
It was the kind of meal that made you feel connected to the island—the sea, the sun, and the people around you.
The perfect midday indulgence.
“How do people live here and ever want to leave,”
Lena asked.
“I don’t know. It makes it difficult to go back to the city—as much as I love it,”
I admitted.
“I could easily move painting to Greece. Please, twist my arm,”
she said. I believed her. She was just wild enough to do something like that and not think twice about it. Could I do that? Was I at a point where I could embrace change? Pick up and move my life somewhere else? There was nothing really anchoring me anywhere, but I wasn’t certain I could. I wanted it to be a yes, but I felt nervous even considering it. I didn’t even have a list of things to hold on to—threads of a life rooted somewhere. I had zero excuses.
“I’m planning on opening an office in Paris,”
I blurted out. Was I trying to convince myself I could embrace change?
“Yes,”
she clapped excitedly. “That’s such a great idea. Plus, you go to Paris all the time already. This makes sense. Will you find an apartment, too?”
She was supportive in all things. I could have told her something outlandish and if she sensed my passion—she was going to push me. Did more Lena’s exist out there? Or did I have the only one. I believed she was the only unicorn amongst the horses. But I found her. I loved her.
“Probably, plus mom can use it until she finds a place she wants to settle in,”
I said thoughtfully.
After our meal, we wandered aimlessly through the streets, enjoying the vibrant energy of the place. We stumbled upon an art gallery showcasing works by local artists. The paintings were stunning, capturing the essence of Santorini’s beauty. Lena and I made a mental note to return and maybe even buy a piece to remember our trip. She wanted to buy something local to take home—a quality I loved about her.
We decided to head to Skaros Rock, a dramatic outcrop of land offering a spectacular view of the caldera. Even with the wrong type of shoes, the hike wasn’t too difficult, but it was steep, and as we made our way up, the air felt heavy with anticipation. We took our time, pausing to admire the view, snap photos, and flirt with a few more handsome strangers along the way. At the top, the view was worth every step—blue seas, white villages, and the sun-soaked cliffs stretching across the horizon. Lena and I sat on the rocks for a while, watching the world below us and soaking up the freedom of the moment. We both took our shoes off for the walk back down.
As we walked down, the air still warm from the sun but cooler now with the evening breeze, Lena and I fell into that comfortable silence we’d perfected over the years. I could hear the distant sound of waves crashing against the rocks below, but it was her voice that broke the quiet, soft and serious.
“You know,”
she started, her pace slowing, “I’m really glad you came here. Not just for the adventure or the business stuff, but because… I think you needed this. You’ve been carrying a lot, Charlie.”
I glanced over at her, catching the concern in her eyes. I knew she could sense it—the weight of everything I’d been juggling, the remnants of past relationships, the pressure of my career. She always knew.
“I know,”
I said, my voice quieter than usual. “I think I just… I don’t know how to let it go sometimes. Like, I’ve spent so much time trying to hold everything together, and I can’t tell if it’s because I’m afraid of what’ll happen if I don’t or because I just don’t know how to be anything but strong.”
Lena stopped walking, turning to face me. Her expression was gentle but firm, the way it always was when she knew I was holding back. “You don’t have to be strong all the time. You don’t always have to be the one who has it all figured out. It’s okay to let go, to admit that you don’t have to carry the world on your shoulders. You’re allowed to just… be. You’ve done enough, Charlie.”
I looked down at the ground for a moment, trying to absorb her words. The idea of releasing control, of letting things unfold without trying to direct every moment—it was terrifying. But part of me knew she was right.
“I don’t even know what that looks like yet,”
I admitted, my voice barely a whisper. “But I think I’m starting to see it. Maybe this time here is about learning to let things happen, without overthinking it.”
Lena smiled softly, giving me that knowing look she always gave when she was proud of me, even when I didn’t fully believe in myself. “You don’t have to have everything figured out right now. But you deserve peace, Charlie. You deserve a life where you can just be happy, without the stress of having to make everything perfect.”
I smiled, feeling a sense of calm I hadn’t realized I was missing. “I’m starting to believe that.”
We started walking again, the weight of the conversation lingering but somehow lighter now. The sun had almost set, casting a golden hue over the island. For the first time in a while, I felt like I was heading toward something good—not just for my business, but for myself.
Lena nudged me with her shoulder. “So, tell me more about Luca. I know you’re holding out on me.”
I laughed, grateful for her ability to lighten the mood when I needed it most. “Oh, you want more details? Okay, well...”
I told her more, but still not everything. Some of those parts were meant just for me to keep.
As the sun began to set, casting a golden glow over everything, we found a perfect spot to take more pictures. The backdrop was the breathtaking landscape of Santorini, with its white-washed buildings, blue domes, and endless sea. Lena, in her colorful strapless maxi that moved easily with the breeze, looked like a goddess. We took turns capturing each other, laughing and striking poses, reveling in the sheer beauty of the moment.
I loved this new version of myself. Carefree, spontaneous, and living in the moment. I felt complete, whole, like I should’ve felt always. I smiled constantly. I was so grateful for this time with Lena and the memories we were creating. By the time we made it back to our hotel, it was early evening and the day had already been everything we wanted. But we weren’t done yet.
The night was just beginning. We freshened up quickly and headed back to Koo Club. The energy of the place hit us as soon as we walked in. The music was a mix of contemporary dance and classic Greek beats, and the crowd was a mix of locals and visitors all out to have a good time. Lena, ever the social butterfly, quickly attracted the attention of a few Greek men, while I hung back, nursing a Santorini Sunset, a cocktail made with local mastiha liqueur and a hint of honey. The dance floor was electric, and I let myself get swept up in the rhythm, the buzz of the crowd, and the carefree nature of the night.
As we danced, a few more men approached, but Lena and I were too focused on each other to pay much attention. We joked about our flirting skills and exchanged stories from our past travels, reminiscing about times when we had done the same in cities all over the world. After a few more rounds of drinks and laughs, we decided it was time to move on.
Soon, the shots of Ouzo flowed freely, and by the time we were ready to leave, the bar had become a blur of flashing lights and carefree energy.
As we left, we bumped into a group of local men or maybe the same ones from the club—charming and mischievous, they offered to take us for a swim. We hesitated for only a moment before agreeing. They promised it would be a night to remember, and with nothing holding us back, we found ourselves on the way to Katharos Beach, a quiet, secluded spot known for its black sand and stunning views of the stars.
The air was cool, the night was decorated with bright starlight, and the beach was almost empty. We laughed as we undressed, leaving our clothes in a pile on the sand before slipping into the Aegean Sea. The water was refreshing, the moonlight glittering on the surface, and the waves gently crashed against our skin. It was wild, spontaneous, and exhilarating.
We swam under the stars, the saltwater mixed with laughter and excitement, the kind of reckless freedom you can only experience when you’re with a best friend in a place like this. The locals guys joined us, but it wasn’t about them—it was just about us, the water, and the pure, unfiltered joy of being alive in that moment. I never wanted this night to end!
Luca: The conference is over tomorrow—finally!
Luca: Alessandro and I want to meet up with you.
Luca: And Lena.
Luca: Does that work?