Dating in NYC vs. Dating in Italy

I tend to really empathize with my single friends out there – especially my single friends living in New York City. This place is notorious for being a particularly difficult city in which to date, in part because of the paradox of choice: we have so much choice, that we inevitably shrug off a good person because there are seemingly endless amounts of  other people out there to choose from. Add to that the anonymity of “connecting” with a person in the form of their online persona, and people tend to forget that there is a person behind the screen that they are texting to. It can lead to a lot of frustration, flakiness, lamentation and wondering  – “Where’d All The Good People Go?

I’ve certainly had my fair share of ups and downs while dating in NYC – honestly, it was mostly downs, until I met my boyfriend (click here to read about why he’s a keeper!). I’ve encountered more than enough flakes, guys who have canceled while I’m literally in the middle of getting ready, creeps who have sent cloyingly flirtatious (borderline uncomfortable?) text messages, douchey finance bros only looking for one thing…a couple of nice guys I just never hit it off with, and a few weirdos who still make me cringe.

But as a sort of late-bloomer myself, I didn’t really date until later in life – and I didn’t have my first kiss until I was 22 (!!!). That fact used to embarrass me, but not so much anymore. We’re all on our own journey…and considering my first kiss was in a medieval bed and breakfast with an older, handsome Italian in Italy, I’m pretty sure I had every girl’s fairy tale first kiss, so it was worth the wait 😉

In any event, given that I got a later start than many, my only real experiences with dating are in Italy…and in New York. In fact, you could say that culturally, I “learned” to date in Italy, with Italian cultural norms, and had exclusively dated Italians until just a couple of years ago. There are definitely some differences in dating culture – and I don’t just mean the stereotypical “machismo” that we hear about (though that certainly does exist in the bel paese, to some extent).

This list is by NO MEANS complete or scientific, just my musings on what I perceive to be some of the biggest differences on what it’s like to date in Italy versus NYC.

In Italy…

Talk is Cheap

Having a bad day? Need a pick me up? Then step out onto any street corner in Italy and within 10 minutes, you will face a stream of “You’re so beautiful, where are you from?” and “Oh wow, che bella...” I’ll never forget the time when I was 19 and fresh off the plane, walking through the San Lorenzo market, when one of the vendors (who quite probably was not an Italian, though I didn’t know any better at the time) said “Excuse me, miss!” three times, before I turned around and said hesitantly “Yes…??”

Pointing at the ground, he says, “I think you dropped something.”

“I did?”I answered, my eyes frantically darting around for a dropped wallet or passport.

“Yes,” he said. “My heart…”


I mean if I didn’t just literally walk into the CHEESIEST pickup line there ever was…

You never hear this kind of stuff in New York (which isn’t necessarily a bad thing), and I’ve found that guys are less emboldened to make moves (unless you count the one time I was picked up by a guy I met on the subway). I suppose the negative to this is that you generally know in Italy if a guy is interested or not, whereas in New York, it can sometimes feel like a guessing game (because remember, #options).

Grand Gestures Are “Normal”

My first date in Italy, I was picked up on the back of a Vespa by a charming Italian who plied me with pastries, took me on a tour of the city of Florence at night, and ended the evening dancing at a popular nightclub. Our second date was an elaborate dinner of Florence’s speciality ~ bistecca alla fiorentina ~ at a local restaurant, drinks on the steps of Piazzale Michelangelo, and a nighttime drive up to the city of Fiesole, which overlooks the sparkling city of Florence laid out along the Arno River. By month 4 he was whisking me away to the island of Sardinia to spend a long weekend with his family.

Think this happens in NY? Think again…

Typical “First Date” Conversation Almost ALWAYS Revolves Around Cultural Differences

I suppose that first date conversations are generally always the same, to some extent. Where are you from? What do you like to do for fun? Where do you work? Do you have any siblings?

In Italy, at least for an American dating an Italian, the conversation topics generally revolve around cultural differences – and often the same stereotypes that get repeated over and over until they become a boring, hackneyed cliche. At first I found these conversations to be interesting, but later on I more often than not found myself bored saying the same things over and over again.

“Yes, we love peanut butter; no, we don’t eat steak for every meal; yes, we do eat eggs for breakfast but not every day; and unlike in Italy, we aren’t stuck listening to ’80s American pop/rock so no I don’t know that band.”

Put Away Your Wallets, Ladies…

Even when you agree you’re going to split the next check. Even when you offer to pay. If you’re on a first date (and usually a second or third), the gentleman will somehow always find a way to pay. I’m not saying this is exclusive to only Italy, that chivalry is dead in the US, or that ladies shouldn’t offer to and actually follow through with splitting the check or even treating. But I’ve definitely been on my fair share of dates in NY where splitting the check is a given, or the guy pays for dinner with the caveat of “you can treat us to drinks after,” or – the worst case scenario – the guy has invited you to dinner AFTER you split drinks, and then asks you to fork over your half when the bill arrives. If you’re doing the inviting, you should at least offer to pay – leave it up to the lady to offer to split.

Dates Are Usually With “Il Gruppetto”

Italian social culture is strictly defined by the dynamics of the group, or the “gruppetto.” Because of the way the school system is set up, your friends in your class from elementary school most likely remain your friends throughout middle school and high school as well. And because Italians RARELY move (a move from Rome to Milan, for example, would be considered HUGE), your high school friends will also go with you to college in your local city. It’s very rare for Italian students to leave their hometowns to go away to school. As such, it’s incredibly difficult to break into Italian social circles when everyone in the circle has been friends for, quite literally, their entire life. I could write a whole separate post on that dynamic alone, but the point remains: friends are VERY important to Italians – and when you are dating one, your “dates” are more often than not large group outings with the gruppetto.

In New York City…

I should clarify that my generalities relating to the majority of my dating experiences in now way should be seen as a reflection of my boyfriend and our dating experience…if it was, we probably wouldn’t be together!

Romance is Dead

Think you’re getting whisked away on some motorcycle, racing down the west side highway to have dinner on a boat before crossing the Brooklyn Bridge for spectacular views of dreamy Manhattan? Think again.

Now I won’t say that those sorts of dates don’t happen, but they are definitely not a “first date” sort of thing. Or even a second (or third) date. Your first date is most likely going to be a quick coffee, leaving you the option to leave in 40 minutes if you’re not “feeling it.” Or he might suggest drinks…located somewhere conveniently close to his apartment (and not for the reasons you think–more for the fact that we New Yorkers are selfish when it comes to subways and commute times!). If you’re lucky, you might get dinner somewhere… but unfortunately, so many people are dating SO MANY PEOPLE – at the same time – that they can’t (or won’t) really afford to put in the effort to make a really awesome first date. Which leads me to…

But the Apps are Alive

Do people even meet organically anymore? If so, HOW?! Share with me your ways! Kyle and I have been discussing this for months now…how do grown adults meet people and make new friends, platonic or otherwise? Heck, we even met on a dating app!

Sadly enough, it seems like the very thing that brought us together is actually a hindrance to many relationships. Constant swiping means that no one really puts much thought or effort into one person or one date – if a person doesn’t like one thing about somebody, swipe left, no second date – you’re wrapped up and tossed into a basket of deplorables in favor of the next closest option.

App culture is not necessarily New York specific, but it does tend to thrive more in urban environments – and is definitely not as ubiquitous or accepted in Italy, where apps either (a) still have the associated “stigma” of online dating, or (b) are used primarily for casual hookups.

Dating Practically Requires a Trust Fund

Okay but seriously…dating is freaking EXPENSIVE in New York! An average dinner for two (and I’m talking like…one cocktail each plus two mains and a dessert to split) could put a fella back upwards of $80-100, easy. It sort of explains the frequent “coffee” or “happy hour” dates – if you’re dating ONE person it’s bad enough, let alone juggling multiple dates per week (This partly explains why my boyfriend [lovingly?] refers to me as his “expensive pet”). You aren’t getting any 4 euro pizzas over here!

Finance Bros Are a Thing

Unfortunately…finance bros are ubiquitous in New York. You’ve probably seen them – hair elegantly coiffed (better than mine!), shoes shined to perfection, wearing crisp blue Armani suits and brown leather dress shoes, or perhaps a Patagonia vest over a buttown down dress shirt, pants, and loafers on a more casual day. This is the “midtown uniform” (no seriously…there is an entire Instagram account dedicated to the midtown uniform), and it will haunt you in your sleep.

So what’s the aversion to the well-dressed, well-off man? ATTITUDE. Cockiness. A general “richer-than-thou-and-therefore-better-than-thou” demeanor. A sense of entitlement and belief that they can get away with anything because their crap doesn’t stink. Thinking that they control/own the world – that they can have whatever they want because they can buy what they want. I wish I could say it wasn’t true, but more often than not…it is.

It’s funny, because you see men in Italy dressed a HECK of a lot better than men in New York and yet…the Italians don’t seem to make a big deal out of it. Perhaps because a well-dressed aesthetic is simply a part of the national culture and not something that distinguishes the “elegant urbanite” from the “country bumpkin.” Just speculating, of course…

Guys Generally Move a Bit Slower

In Italy the men will wine you and dine you…and then expect you to to hop into bed with them pretty much immediately after you finish your tiramisu.

In New York (with the exception of the aforementioned finance bros), guys move a bit slower and are generally more respectful of your boundaries. Where an Italian might try to go in for the kiss even if he senses you’re not keen on it, New Yorkers tend to take things a bit slower, and at least try to respect/pick up on your body language and cues.

In Both Countries…

Dating kind of sucks. I know he’s kind of controversial to mention right now but Aziz Ansari’s book Modern Romance really lays out what it’s like to date as a millennial in the modern era  – how the paradox of choice and feeling like we have to be optimizers leaves us feeling empty, unsatisfied, and unfulfilled, always with an eye out looking for the next best thing, forgetting that a bird in the hand is better than two in the bush.

Sometimes I think it would’ve been so much easier back in the 50s or 60s, where you married the boy down the street from your family after high school, and started a little family of your own, no questions asked. I know that’s a super idealized, probably fictitious reality, and I certainly don’t want to spend my life as Judy Cleaver, but it does sound a little less complicated.

If you’ve ever lived/dated in a different culture, I would LOVE to hear some of your thoughts and experiences. What were some of the most shocking cultural differences? How did you adapt? What were some similarities? If you’ve lived in or dated an Italian, do you agree or disagree with my assertions? And my fellow New Yorkers – what are your thoughts on dating in this city? Please share your thoughts in the comments!

Click here to read my most popular article to date on what it’s like to date after a heart-wrenching breakup.


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