Lessons From a Tinder Date in Florence, Italy

A city full of yearning

As I wandered the cobbled roads of Florence alone, I was in awe of all that I saw. The beauty of the buildings told me one thing — whoever designed this city knew what love was and felt it very deeply.

While I love to travel alone, the image of walking these narrow streets during a breezy night with a woman couldn’t leave my mind. So I dusted off the Tinder app.

Mind you, I’ve spent months actively using Tinder without ever going on a date so I had no expectations since I only had one night. I did some swiping and continued my strolling through the streets.

I ended up matching someone very quickly, but I thought nothing of it. Since time was of the essence, I went to send her a message and break the ice only to realize she already sent one.

An incredibly rare sight so I sprung into action and worked the charm with voice notes. We sent less than 10 messages in total. I told her I was leaving home tomorrow morning and that we could only meet right now.

That’s where I was expecting the conversation to end, as it usually would. Instead, she sent me her location. Candidly speaking, I had lustful intentions, but I’m never cutthroat about it. She was living in Florence, so she knew a spot. A nice outdoor bar with couches.

When I arrived, we did the timid hug and greeting, not knowing what to expect. We barely spoke prior. What if there’s zero chemistry? Her bio said she was into meditation so that gave me hope.

We sat and chatted the typical small talk. It felt effortful, so we got a drink to loosen things up. It was slightly excruciating until she mentioned her time in Oaxaca, Mexico. From then, the conversation flowed.

We effortlessly weaved between the bitter-sweet experiences of solo travel, meditation retreats, psychedelics, dating apps, loneliness, validation, and addiction.

I asked her how it feels when someone matches her on Tinder. She said it felt like nothing. I challenged her answer, not believing that.

“The feeling of someone liking the way you look can never compare to the feeling of someone truly seeing you.”

I noticed I was drinking melted ice from my glass. We needed a second drink. As I was paying, I realized we didn’t. We were in a flow and it felt great to know that it wasn’t because of the cocktail.

We disagreed on many subjects and it felt great because we just listened. It didn’t feel like boxes were being ticked on a first date. But my wandering, lustful mind couldn’t help but wonder where the night would take us.

Perhaps I’d walk her home and she invites me into her vintage, high-ceiling apartment and I’d sleep there rather than in a bunk bed hostel.

Do I want sex or an intimate connection? Does sex equal intimate connection? After drinks, she took me to her favorite gelato spot, and we ate on a bridge overlooking the glistening water facing the Ponte Vecchio, a famous bridge.

“Legend has it,” she said,

“When Hitler bombed Florence he specifically made sure not to bomb that bridge because he liked it so much.”

Regardless of if it’s true or not, my perception of what I was looking at changed for the better. I became more curious and observant. There are so many stories beneath our feet that we will never know.

She was quite close to me, her knee grazing mine. The lustful mind came back. I saw the surrounding couples holding each other on this scenic bridge. Should I put my arm around her and kiss her like they do in the movies? What if that ruins the vibe? It has in the past.

So I just let it breathe, and we kept talking. It was around 1 am, and she wanted to head home. She asked me to walk with her. That night, we walked through the narrow, cobbled streets of Florence, just like I hoped for earlier that afternoon.

The vibe for that night wasn’t what I initially hoped it to be when I installed Tinder. We stopped at lit-up art stores, marveling at the beauty and detail of the products. We talked about the rushed nature of coffee and the slow, timeless nature of tea.

That took us to her apartment door. I don’t know the name of the type of door but it looked like one you’d see in Italy. After we hugged, we sat in an awkward pocket of silence for a moment. To which, for some reason, I asked to kiss her.

A difficult look covered her face.

“What’s the point?” She said. “You’re leaving tomorrow morning.”

I tried to answer that question on my bike ride back to my hostel. Why is physicality perceived as the pinnacle of connection? The depth of connection we exchanged solely through conversation superseded many sexual encounters I’ve had in the past.

Was my night spoiled because we didn’t kiss? No. Would my night have been better had we kissed? Yes feels like the right answer. But only kissed? Would that have just left me dissatisfied? We hugged, and we wrapped our bodies around one another, what’s so great about lips?

Is sex truly what I wanted? Or did I want to feel seen by a woman? How would it have felt jolting out of her apartment a few hours later to catch my train? On the surface, it felt like rejection. However, beneath that was a mirror to my face.

I’ve been able to get away with many lustful nights by asking that simple question I asked her at her door, robbing me of the gift of self-reflection. She handed that to me, and I was ready to receive it.

As we may travel to escape ourselves, it’s fascinating to see what stays along with us no matter how far we go.