An American Male on the Make in Italy

story and photography by Michael Housewright

I have studied, lived, and worked in Italy off and on for most of my adult life. My most enduring fantasy through the first fifteen years of Italy travel was to meet, and ultimately court, a beautiful Italian girl. I imagined I would charm her with my wit, interest in her culture, and mastery of her language. Unfortunately, I never possessed the knack for striking up an easy conversation with a woman I did not know and to whom I was clearly attracted. Being a straightforward person, I have always lacked the subtlety and easy rapport with women that men of romantic talent seemed to me to possess. However, my self awareness did not stop me from trying, and frequently failing in my efforts to woo. 

Attempts at humor, small talk, and questions about local customs all led to feigned laughter and awkward pauses when I approached Italian women in public settings. I thought I was supposed to be the exotic foreigner, mysterious and fetching. I felt more like the class clown rather than the quarterback. While sometimes funny, I felt I could never be taken seriously as a contender for an Italian woman’s affection. Perhaps I was not aggressive enough, not fashionable enough, or just not that cool. I basically had no game and I believed that maybe I never would.

Over those fifteen years my Italian language improved, I ditched my Nike basketball shoes for stylish European loafers, and above all, I made certain to always wear outstanding Italian sunglasses. Each stage of my transformation would yield a smidgen more self confidence self-confidence and over time an elevation in my skill set. 

One day, as I meandered through the mire of sharply dressed locals at the Spanish Steps in Rome, after having just picked up my newest pair of fabulous POLICE brand shades, I met an Italian girl. At least 5’8”, a towering height for an Italian girl, she was selling standard-issue Interlotto (lottery) cards. Her hair was raven black, shoulder length and stylish. Her nose was longer than average, sharp at the end and in a direct line to her deep brown eyes. Her build was lean, her clothes were perfect, and although she could have been no more than 25, in her Hipster glasses she appeared every bit of 30. When she tapped my shoulder and asked if I wanted a ticket, I responded back in rare perfect Italian that I was in fact not from Italy to which she immediately replied, “bugiardo!”

A liar?  I began to laugh, thinking how preposterous it was that she did not believe I am American. I am six and half feet tall, pale as an iceberg and … wait a minute. The facts were clear. I fooled her. I genuinely, and at least for an enduring moment, made her believe I was Italian. At that instant I had game and I ran with it. 

I proudly told her that I was American and she broke into a wide smile and apologized for bothering me. I took the bait and said that I was flattered she would believe I was in gamba (very cool).  She pulled the lottery tickets close to her and assumed a conversational stance. We exchanged pleasantries, occupations, and I told her briefly what had brought me to Italy. She expressed to me once again that my Italian was excellent (who was the liar this time?) and then asked if I wanted a coffee. Holy Cow! An Italian woman had just asked me to coffee. I was floored, but for once I remained cool. I composed myself, knowing the game was finally afoot. 

I considered asking her if she would like to have dinner instead, and then I could take her for coffee in the morning. I thought about how we might laugh, and eat slowly over a bottle of Brunello di Montalcino. I pictured us walking arm in arm through some remote neighborhood piazza where kids kicked soccer balls and teenagers smoked stolen cigarettes. I finally had the chance I had been dreaming of for all those years. And yet, when I opened my mouth, I said no thank you, smiled, and went on my way.

I was already in my mid thirties and my travels to Italy had increased to the point where it was no longer an exotic vacation. The boot had become a place that I could actually feel at home. I had several good friends in cities and small towns up and down the peninsula. I could speak the language well enough to establish a conversation and even make the occasional joke. I had, in effect, become a bit of a local, and I liked this very much. The lottery girl had believed for an instant that I was Roman, and this was so satisfying and surprising that my long awaited chance to finally woo my Italian dream girl became anti-climactic and even frivolous to me. 

One of the primary reasons I have chosen to travel so frequently is the potential for revelation. No matter the plans and goals I set for any destination, I am typically amazed how much more I learn about myself and the world than what I had originally intended. In this case, I had always wanted to meet and strike up a conversation with a beautiful Italian woman. When this finally happened, I realized I had achieved the far greater goal of no longer looking, feeling, or behaving like a foreigner. I discovered at the moment when I declined the coffee invitation that I was not blowing some one-time chance. Coffee invitations and in-depth interactions were no longer fantasies, but very real possibilities. After the young lady departed, I paused for a moment, and then climbed a few of the Spanish Steps. I took a breath, turned around towards the open piazza and strolled down to the street, proudly showing off my new sunglasses, like a true Italian.


Michael Housewright is a professional eater and storyteller. In his blog, The Blissful Adventurer, Michael chronicles his life eating his way around Italy, working for 15 years in the food and beverage industry, and shooting thousands of images while living on the road since 2011.  Michael is launching a series of iPhone imaging workshops and travel programs in San Francisco and Puglia, Italy this year.

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