The Story of When I Tindered In Milan


As much as I wanted to be a Blair during this trip, I was so, SO much a Serena.

I tried to be a Blair. I worked Fashion Week backstage at the shows, running around quickly to capture content, typing furiously on my phone, emailing editors for exclusive pics, bossing around the photographer to get the right shots. I accessorized each outfit, drank espresso and walked around with purpose. I even ate breakfast at The Four Seasons the morning after I watched Kendall Jenner slay the Versace show! But as Blair as I was during the day, my Serena ultimately took over each night and I turned into the boy crazy, no-fucks-given, no regard for safety, or caloric intake, blonde-haired, short dress donning, chain smoking heartbreaker I’d been robbed of being most of my early twenties.

But I knew I’d be a Serena there, or, at least a generous combination of the both of them.

So Tinder in Italy is pretty popular. The guys on there are even more active than guys in NY on the app. And they’re certainly much more generous with “superlikes” than are American guys. Bastards.

I traveled with a co-worker, and without a super ton of downtime, or the knowledge of the right bars to frequent to meet young people, I figured if I wanted a European romance to write about, I’d have to find one the true Gen-Y way. On the app.

After matching with a good amount of seemingly handsome, educated and employed Italian twentysomethings, I began to message eligible tour guides “show me around?” with the American flag Emoji beside, signifying my foreignness outright. My photo, which is me sun-bathing and drinking rosé in a bikini top and denim shorts says enough about A, my dating profile strategy (tits before wits) and B, my positionality as the ultimate blonde, American girl.

They were definitely interested, and I got 20 messages within the first day from guys offering to buy me wine, show me around, and hitting me with crazy, cheesy flattery. One guy even sent me an itinerary complete with a Google maps route that we’d follow on his guided tour.

My love though, the one and only guy I chose to go out with, messaged me a GIF of a fat kitty in space sipping on a bottle of Cab.

IMG_0599Pretty easy to see why he’s the one I agreed to meet out. I mean… a cat GIF. The promise of wine. The way he simply and assertively said “stay free tonight”(sometimes I actually prefer a direct command). It was game over. After looking at his profile and realizing he was a hipster of Brooklyn proportions, and a handsome one at that, I was excited to meet up and begin my Serena-ing around Milan.

We exchanged info and began to message on What’App proceeding the meeting. I was at dinner with a few editors who were also working Fashion Week, (Glamour and Allure to be specific) and after a bottle of red and a few limoncellos post dinner, I was more than ready to meet this cat-gif sending stranger.

I was standing outside of the restaurant smoking a cigarette when he walked up to me…. Made this mofo meet me where I dropped him a pin because A, I don’t know this city at all and B, gotta get ‘em in that mindset immediately so they understand how this whole thing is going to work. 

I say jump….. you know?

I can’t remember what we first did after we met, maybe walked a bit, maybe stopped into a bar, it’s kind of fuzzy, but the next thing I remember we were laughing and walking through this park area where there were buildings that were totally normal to everyone around us and completely gorgeous and awe-striking to me. We had easy conversation, even immediately. It was light, flirtatious, fun. The moments of non-understanding between us were an immediate bonder, as I’d laugh at random American words or phrases he didn’t understand, and as he thought my desire to Snapchat areas of the city that are hardly known at all “adorable”, and “super cute”. I immediately felt at ease, despite my co-workers and friends warning me tirelessly about the men in Italy and the unsafe nature of European dating, or stealing, or sexual harassment. About 20 minutes into our walk when I ask him what we’re doing he pulls a straight up Aladdin and says to me, “do you trust me”.

Naturally I flash a smile and say “of course”, because I had deliberately decided to turn off the voices of worry in my head about 15 minutes prior. It was all a big part of my whole “living in the moment” thing post-breakup.

About five minutes later we show up at a museum looking building, with a wide entryway and extremely bright lighting. It looks closed, as it’s empty and it’s fucking 11 at night so I’d be beyond surprised they’d have Picasso’s work on display at such an hour, but he says something in Italian to the guard and the guard smiles and allows us to go in. After moseying for way too short a period, (I just genuinely don’t have the appreciation I should for art and sculpture), he ushers me into the elevator and we emerge at a rooftop bar/restaurant.

“YAAS”, the voice inside my head squeals. I mean this is certainly going well and all but at this point in the night I’d love a glass of wine to loosen up and help me get the thought that he might legitimately murder me out of my head.

A glass of red in one hand and a cigarette in the other, we sit outside and chat for a bit. He tells me about his apartment and how it’s also his studio, how it’s nice, has great lighting, etc. The way he speaks about it almost implies that I’ll see it, but I laugh almost snobbily thinking, “yeah, right”..

(Little did I know I’d wake up there five days later practically in love with the place).

After the drinks, we went down and began walking around Milan. I was promised a tour, and Milan at midnight is empty and beautiful, so I was thrilled. By this point we were getting along almost too perfectly. Like a romantic comedy where my character, played hopefully by some young Margot Robbie lookin’ thing meets some charming Penn Badgley type and they flirt for the first, I don’t know, eleven minutes of the film before furiously making out outside of a bar, or inside of an impeccably well-decorated apartment. That’s honestly how it felt. After playing this game for what was probably an hour or two, he kissed me.

We were in the street and he was showing me his license so that I could take a picture on my phone in case anything “mysterious” happened. Something I was completely serious about but framed in a playful enough way that he thought it was equal parts funny and adorable. Anyway, I was looking at his license and we were standing pretty close… I looked up to ask him a question and mid-sentence he grabbed my face and kissed me.

It was legitimately a rom-com kiss. Slow and tentative at first, growing into something from far PG within a few minutes. I pulled away and probably did some quintessential girly laugh, hair-touch, lip touch, stupid thing before walking away and attempting to act normal.

Next he said, “so you’re journalist?”, smiling and not wanting to talk him through the confusing nuances of social media marketing and how that relates, (or doesn’t) to my journalism degree, I smiled and said “yes!”.

He took my hand and smiled and a few moments later we were outside of the office of Vogue Italia and he was showing me where the Editor in Chief sits.

We spent the rest of the night kissing and laughing outside the Duomo, and when he walked me home our kiss goodnight lasted seemingly forever but hardly long enough.IMG_0415

By the time I finally laid down to go to sleep, my jet-lag and excitement dueled inside of me, both fighting the other for ownership of my status of consciousness. After a text goodnight from him appeared on my phone I finally passed out for a wonderfully brief four hours.

The next day was similar to my first with work. Fashion week excitement and hustle, mandatory sight-seeing and carb-bingeing, total exhaustion and uncomfortable dehydration, (they don’t fucking drink water over there) and the hope that maybeeee I’d see my Italian bae again for another night of Frenching in Italy.

He asked me to dinner, but I couldn’t say yes. “I’m going with my co-worker I explained him, and to that he said okay, and to write him that night when I was free. At about nine p.m. he texted “here” so I went outside to meet him. He was in the driver’s seat of a car he rented, and I was a bitch and ruined it.

Realizing this whole play-by-play style of recap is exhausting for both me, and the reader, (hi to any of you who are still with me), I’ve decided I need to SOMEHOW make this much briefer.

I’ve set the stage. You understand the basics and now I can spend the next 1500 words speaking on how sweet and sprung he is, and how I legitimately rival Suess’s “The Grinch” for size of heart.

So he rented a car because he had a plan to show me Milan’s best sights, and special places only locals know about. I basically threw a bratty fit telling him that I didn’t want to be in a car, I didn’t feel safe, I wanted to drink wine, etc, etc.

After an hour or so of this argument and him apologizing furiously despite me being the only one being a true bitch, I realized I should perhaps salvage the evening and we settled on going to a wine bar to drink away any residual awkwardness. (He may or may not have gotten hot-headed with me in the car when I spoke out about my disapproval of this plan).

We had a nice bottle of wine and talked over candlelight. The night actually turned out to be one of my favorites in Milan.

Okay- trying to stop with the play-by-play.

Let’s just say, that night didn’t end at the wine bar and by 2 a.m. I was playfully kicking him out of my hotel room so that I could awake for another day of Milan Fashion week hectic-ness in just 5 hours.

The following night was a late one for me, with work. But still, after my long and trying day, he showed up to my hotel at night so say goodnight and this time with a present.

Naturally I had to invite him up.

It was about this time in my short week in Milan that I realized this guy was so beyond sweet, and more into me that probably every guy in NY I’d ever be meet. He showered me with affection, kissed me like he was hungry for me, brought me presents and would do whatever I wanted, and a million other things.

He’d say to me, “you drive me crazy” and kiss me in a way that proved his words and then some. UGH.

The following night he cooked me dinner. And I don’t think saying “he cooked me dinner” does it justice. I showed up in a tight, off the shoulder black dress, with a leather choker necklace and the kind of make-up Gigi Hadid would wear during a cover shoot, to the aroma of the actual best cuisine I’d experience my whole trip. His apartment was sprawling, gorgeous, minimalist and decorated very well considering he’s a guy and all, (though I’m learning European men stray far from the heteronormative gender roles of American idiots). His place could probably go for a few million in the West Village, considering it’s spaciousness, natural night, floor to ceiling window wall and large rooftop porch. I tried to act equal parts impressed and low-key, but my awkward nature was luckily something he so apparently found endearing, so I quickly drank Pinot Grigio and we started our night.

We cooked, laughed, drank, smoked and talked all night. He gave me a big shirt and boxers to sleep in and though we didn’t end up going to sleep right away, when I woke up I instantly felt like I didn’t have enough time there.

This is where my previous post begins, where I did my whole bitchy, spoiled brat thing, but luckily this wasn’t my last day in Milan.

So I left, went back to my hotel and tried to shower long enough to scrub away the disgusting romantic feelings that were active in my body like a virus, but no amount of organic soap or steam could rid me of the butterflies that set up camp in my stomach.

Again, we talked all day and met that night- my final night in Milan.

He came up into my hotel room and we shared a nice time, but like the Cruella DeVille that I actually am, I kicked him out preemptively. “I’m tiredddddd”, I whined. “I honestly need sleep tonight”, I justified. He seemingly understood, but still left with such a disappointed visage that I almost ran out after him. Of course, I didn’t though- that’d be something sweet and nice and apparently I’m visibly incapable of acts of kindness.

Anyway, I was feeling too attached to him, and too strange about the night we’d shared before. Was that too soon? I had just had my heart broken one month to the day, to the fucking day, the night I slept with him in his apartment, and so that last day I was feeling all types of confusion and emotional unsteadiness.

I got on the plane and paid for Wifi to WhatsApp him. “I’ll misssss you”, I typed. I meant it. So smart, so creative, so handsome and charming and endearing. I wanted to jump out the plane window with the realization that the most romantic experience I’d ever have had just come to it’s sweet, bitter end, but luckily I couldn’t have been more wrong.


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