Dating Italian Men – Hilarious Encounters with Italian Stallions

Dating Italian Men
Ortigia Island, Sicily

Italian men feature on many female traveller’s adventure to-do lists just as much as say, a trip to the colosseum, taking the perfect selfie in front of the Trevi fountain or uncovering where to eat the best pasta in all of Roma. (Okay maybe let’s not say “to-do lists” – we are ladies afterall… I guess?!) There are few nationalities more charming, handsome and as renowned for being incredible lovers as the Italian men.

A British or American guy may invite you over to Netflix and chill, but an Italian man will offer to teach you to cook carbonara while you drink exquisite local wine, or invite you on a late night picnic by the sea. For romance and charm factor, Italian men top the leaderboards. After living in Italy on several occasions (in Milano, Napoli and Sicilia), I thought I’d share some of my experiences and encounters with Italian men.

Warning! It should be noted that Italian men are very much aware of how charming a lot of foreign women find them. They take great pride in their Casanova reputation and believe that women find them so utterly irresistible that we will have no qualms about jumping into bed with them immediately.

Hilarious Encounters with Italian Men

Dating Italian men
Living in Naples, Italy

My background is actually British & Italian. When I was much younger, I was proud of my Italian roots and always thought of Italian men as some kind of  Mediterranean Gods. Nowadays I find the things that they say when trying to approach foreign women all kinds of hilarious. Summarised below are some of the most comical encounters I had with Italian men when I lived in the motherland.

#1 Hey Sexy Lady… Oh Wait, You Old AF

It’s summer 2018. I’m living in Sicily. I’m sitting on platform one of Catania Centrale waiting for the morning train to depart for Syracuse. I am mid-way through wolfing down a chocolate croissant, sporting a chocolate sauce moustache with croissant flakes in my hair, down my shirt, in my eyebrow – croissant flakes pretty much everywhere.

I peer around to make sure that no-one is watching me devour this croissant like an ogre, and notice a Sicilian guy staring at me. Horrified that someone seems so transfixed by my croissant gobbling, I try and make a conscious effort to eat like less of a trollop as I continue.

The next thing I know, this guy has migrated to the spot right beside me and is asking for a cigarette lighter. I replied and told him sorry, but I don’t smoke. Now that he has an “in” to talk to the girl with chocolate all around her mouth (but arguably questionable standards of women!), he tells me that I am beautiful, then asks me “quanti anni ha?” (“how old are you?”). Our conversation follows like this:

Him: Quanti anni ha? (How old are you?)

Me:  Io ventotto anni  (I am 28!)

Him: *Loud dramatic gasp like when the murderer is revealed at the end of Scooby Doo”

Him: You said that correctly in Italian, yes? You are 28?

Me: Yes exactly

Him: Oh. My. God. Oh my god!

Me: Well I don’t think 28 is really that old

Him: You just don’t look SO old. I am 22. You are too old for me.

Me: Oh well I wasn’t interested in you.

Him: Bye madam!

At least I could go on to eat my croissant in peace, but honestly probably the most extreme reaction to being 28 that a person could ever encounter. The man could not get away fast enough!

#2 But Wait… I Have Oil!

I was living in Naples and decided to treat myself to a few days in Lake Como. Early in the morning, I wandered around the lake to take some photographs and explore Como town before the crowds. When I sat down in a local place to have an early lunch, a Sicilian man plonked down beside me uninvited.

I had my weekend tote bag with me and he asked if I was leaving so soon. I told him that I had to get back to Naples, to which he offered that I could stay with him and that he would even give me a massage, since my bag looked so heavy to carry around! I politely declined, and said I had to leave to get a train soon, to which he exclaimed “but wait!!!! I have oil!!!!” He yelled it plenty loud enough for pretty much everyone in the place to hear him and turn around.       

#3 The Complimentary Tour Guide   

I was living in Napoli, and had been living there for quite some time. Since I worked from home a lot as a Digital Nomad (Italians aren’t really big on the whole “sit down” coffee culture – it’s pretty much chug down your cappuccino while standing and then be off), I ventured out from my apartment lair to go and get some cakes from the local bakery (full on slob status).

As I was strolling along, some middle aged balding Italian man latched on to me, seeming to immediately recognise that I was foreign. He asked the usual “What’s your name? Where are you from?” I just blanked him and stared forward as if he didn’t even exist. Like Bruce Willis’ wife in the sixth sense. This technique usually works in getting men to leave me alone but this dude was persistent.

The older guy had clearly just come back from the supermarket, as he was walking along swinging a bag filled with milk and groceries, a huge french baguette protruding out the end of it. As we walked along the seafront of Chiaia district, he started explaining the sights around me and their history. As I picked up my pace, he picked up his. He was recalling dates and events so well that I thought that I was on a Rick Steves walking tour.

After a few minutes, I abruptly turned around and asked him to leave me alone. He looked shocked, adjusted his glasses and yelled “WELL YOU ARE TOO SMALL ANYWAY”. Excellent.

#4 Love at First Sight

Before moving to Naples, I spent a few weeks there in 2015 , I went to a lot of Couchsurfing meetings to try and meet locals and expats living in the city. Italian men in general, but especially Neapolitan men, are quite enamoured with foreign women. One guy happened to be at two of the meetings that I went to over the course of a week or so. He stared at me, head in his hands, with little puppy dog eyes as I ate pizza like a barbarian and dribbled melted cheese everywhere.

As my trip came to an end, he asked me if I would like to move in with him rather than go back to England. Keep in mind that I had only met this man twice at this point, and spoken to him briefly in the company of other people.

“I have to go home” I told him

“But I love you!” He returned

“You don’t love me, we just met”

“I love you!”

#5 Lost in Your Eyes

I’m shopping for groceries in Catania, Sicily. As I stand by the fruit and vegetables examining the quality of the tomatoes, some guy sees me and leans towards within an inch of my face. As I almost give myself whiplash moving my head backwards, he says “wowwww”

I look at him puzzled, and he exclaims “Your eyes! They are so blue! Are they real?”  I respond and tell him that they are. “They so blue like the sea!” he exclaims excitedly. “I want to swim in your eyes, to be lost in your eyes” Umm okay. I back away slowly clutching my tomatoes. “So blue!” he is still muttering.

#6 The Eight Wonders of the World

I am sitting on the bus from Naples to Bacoli – a cute little beach town in southern Italy. The bus drivers are slightly older gentlemen and are in the process of switching shifts. I’m sitting at the front of the bus, and one of the drivers is sitting across the aisle from me. He seems pleasant and chatty, telling me the best places to visit in the area. That is until he tells me that my legs are the eighth wonder of the world and he would like to visit them. Barf.

#7 “Bellissima”

In Naples and southern Italy especially, you are likely to hear breathy mutterings of “Bellissima” from the men that walk by. It can be a little unnerving and strange. Are you supposed to continue on as if you never heard it? It seems that way, and that these men are purely showing their appreciation for female beauty.

Though admittedly some of the Italian men in these examples were rude a-holes, generally travelling through Italy is something of a confidence boost. It is not usually a creepy, uncomfortable approach from Italian men. Even if the locals do not approach you with a cheesy chat-up line, their comments of “bellissima!” or “Ciao Bella!”, their glances and their prolonged looks are more of a compliment and appreciation for beauty, than anything untoward.

Things to Know About Dating Italian Men

Io, Mammeta e tu

Italian men are known for their strong bonds with their mothers. It doesn’t matter if Giuseppe is 40 years of age, his Mum is still likely to be popping round to his place every couple of days with trays full of home-baked pies and leftover food. Besides, she needs to come to his place regularly so that she can do his laundry!

Italian men are still treated like little darling children by their mothers up until they marry. At that point, it’s most likely you that will be ironing his shirts and picking up his pants. Mamma mia!

Location, Location, Location!

Honestly, I notice a lot more approaches from Italian men in the south of Italy compared to say, Milano, Venezia or Firenze. Sure, Italian men have a bit of a reputation everywhere, but the men in southern Italy are much more direct and shameless in their approaches.

There is a significant cultural difference between the north and south of Italy which is important to be aware of. When you venture southwards of Rome, it is almost like being in an entirely different country as compared to being in the north.

Northern Italian men are chicer and more fashion-conscious – he will be there in his pale Blue Prada suit, that perfectly matches his footwear, his wristwatch, and his man bag. Southern Italian men are likely to be a little more rough and ready.

Italian Men are Family Orientated

Italians are very family orientated and close even with non-immediate members of their extended family. The nice thing about dating Italian men is that they are generally very thoughtful and inclusive.

I dated a Neapolitan man for a while in Naples, and he made great efforts to try and make me feel welcome by introducing me to his friends and family and helping me to feel settled. I don’t believe that he was just an exception.

Are All Italian Men Womanizers?

It’s no secret that Italian men can be flirtatious. I mean, this article is just one example of that! While there are all these theories and statistics about how Italian men are notorious cheats and lotharios, it really does depend on the individual. I have many Italian friends who are in committed relationships, and although obviously I cannot know every minor detail of their situation, I cannot imagine some of these people as the type to cheat.

It’s a shame that negative generalisations and stereotypes like this affect Mediterranean men so much. Is that to say that British men are the perfect partners who never cheat or disrespect their wives and partners? I don’t think so.

Have you had any experience dating Italian men? Any comical encounters with the locals while travelling in Italy? I would love to hear your perspective!

Melissa Douglas

Melissa Douglas is a British Travel Writer and Blogger based in Athens, Greece. She writes for numerous high profile travel publications across the globe - including Forbes Travel Guide, Matador Network, The Times of Israel and The Huffington Post.

14 thoughts on “Dating Italian Men – Hilarious Encounters with Italian Stallions”

  1. Haha! I love these stories. I’m blonde and was told Italian men have a thing for blondes (since we aren’t common there I guess?) and I ended up meeting a leather craftsmen while I was in Assisi. He didn’t think I was too old, but I could definitely tell he thought he was charming 🙂

  2. Well, this is just a bunch of pathetic short stories, because you actually did not date anyone. Even the title is wrong.

    The only argument I do agree with is the warmer approach of southern Italians, the true stallions of the peninsula.

    I am Canadian and every time I went visiting Italy , I really did date a man there, and I can tell that , well, that’s the Stallion experience you did not try.

    I ended up married to a Man from Puglia, gentle father during the day and…still stallion!

    Next time travel wiser and stick the titles to the content.


    • Actually “Jen” I had a Neapolitan boyfriend for a good while. I just chose for this post to be light-hearted and to focus on the humor aspect. In any case, I am sorry that your life is so empty that you feel the need to send nasty messages to strangers on the internet. Hope you find a more positive and productive way to spend your time! Hugs! xo

  3. hahah lol. i loved this article so much. my favorite was number 1, both 3’s and 4. it is very disappointing that people have to be pinned down to certain traits just because of these stereotypical characteristics. Not everyone is like that, it really does just depend on the person. Thank you so much!

  4. I was so happy to read this. I moved to Italy several months ago and thought it was “just me” when 90% of the Italian men I met would invite me to their house literally the first day we met. I’d say around 5% in the first few days and the their 5 lived with their parents and would often ask to come to MY house (not happening).
    Needless to say, I haven’t had any luck with the men here and I’ve decided to stick to foreigners. I know not all men here are the same but apparently I just attract the ones who are all the same lol.

    • Hey Naa! Oh my gosh me too ha. I just generally attract a lot of odd people wherever I go I think, like some kind of beacon lol. There are some very nice Italian men though! I actually met the loveliest guy when I lived in Naples and we just hit it off straight away, but unfortunately I met him right before I was due to go travelling around the Middle East for several months – terrible timing! We kept in touch for a while and I intended to go back eventually but I ended up moving to Greece – what could have been! Whereabouts in Italy are you living? 🙂

  5. I met an Italian guy and we dated. However, he forced me to slept with him on our third date. It was uncomfortable but I like him so I just go with it. and then after the deed, I asked him when was he got tested for STD, for me it was like for safety. Am I wrong to do this. because it seems like he got angry at me. and he now treats me differently.
    What can I do to win him back?
    thank you.

  6. Hi, its my first time here, but i enjoyed reading these. I just got curious because i just recently broke up with a Southern Italian guy from Naples a few days ago. Just want to ask though if its normal for a Southern Italian to be so jealous, and overly suspicious?? He prohibits me having male friends on FB just to cite an example.

  7. Hallo!!i am now starting relationship with an Italian man, I am scared now. hhh i don’t want to go with the wrong person, i am younger than him and i am hoping to love each other forever. Thanks for sharing this story

  8. I was married to an Italian (parents from Naples) who was born and raised in Canada. He was short (5’5″) and extremely insecure (Napoleon syndrome). Aggressive, controlling and stupid af. I couldn’t take it anymore and finally asked for divorce, at which point he made it his mission to bully me and physically threaten everyone in my life who supported me. He also made up ridiculous stories about me to anyone who would listen. Extremely narcissistic. He was a thief and compulsive liar. Never wanted me to leave the house because another man might notice me (oh and that would be MY fault of course… even at 8 months pregnant).

    I dated a few Italians before him and also one after and they all seemed to think they knew everything.

    They always seem to find me (I’m Eastern European) and there are some good qualities but I don’t think I could marry one again due to my horrific experience.


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