“I think you are the most difficult date of my life.” It is a gloriously warm October Saturday evening in Milan and things aren’t going terribly well. We are standing – Stefano, a 34-year-old artist, and I – outside Princi café in the posh Brera district, watching a couple, entwined like pretzels, feed each other ice cream. Stefano makes one final romantic bid by suggesting that we get an ice cream, too, and I tell him I am lactose intolerant, even though I’m not.

It is 7.05pm. I know the time because the duomo, candy-coloured and resplendent behind us, has struck the hour, and I realise I have just heard the death knell of my blind date. On paper, it should have been successful – he suggested Brera, a pretty, pedestrian-friendly mesh of private galleries, cafés and posh shops, because it lends itself to wandering arm in arm. Stefano’s right, it’s couple-friendly; the thing is, I think my date is literally blind in one eye. Shallow, I know, but Tinder’s a dog-eat-dog world. I blame myself – all the photos on his profile were taken from his right side.

I had flown into Milan on BA’s red-eye to experience “Tinder tourism”, the digital version of a holiday romance. This is a fairly new business that sees tourists log on to the smartphone dating app on holiday, which is as seedy as it sounds. Before I’m through passport control I’ve got 10 matches, each accompanied by something lewd.

Tinder is a global success story. Every day, as the founders recently told the New York Times, the app makes more than a billion matches. But while it has undeniably changed the way we interact in the two years since it was launched – abandoning the algorithms of dating sites in favour of snowboarding photos – it will turn out that I’ve come to the wrong place. According to Italian locals I’ll meet, there’s a crisis in dating taking place. Still, Tinder has its advantages: provided you arrange quick meet-ups and keep your standards low, you can cram several encounters into one day.

I am staying at Palazzo Parigi, a cappuccino-coloured palace of a hotel on the corner of Brera, which is where I arrange to meet Fabio for a coffee. Parigi has recently been renovated to a state of frankly absurd luxury. Everything is marble. Flower arrangements teeter on every surface. You can’t move for concierges. To be honest I’m surprised he has the nerve to show up. Then I see him, on the terrace. Boy oh boy, but someone’s a dab hand with Photoshop. I quickly text an excuse and get the hell out.

Later, fate gets its own back. I make a plan to meet a filmmaker over an aperitivo at the Sheraton, in an up-and-coming district near Navigli famous for its nightlife, and steel myself with a negroni at the infamously experimental Nottingham Forest bar. On first sight of Fabio, I am buoyed. Fit, I think, and (after a chat) funny! I think it’s a shoo-in until he announces he’s just broken up with his girlfriend and leaves.

Exhausted, I get in touch with Ilaria Perrone, a 31-year-old Italian blogger, for some guidance. Ilaria has been blogging about sex (and love) for two years and has become quite a figure on the Milanese scene. Last month she was interviewed about the sexual antics of Italian men and caused a furore when she revealed that – gasp – Italian men were not the wining-dining romantics we believed them to be. They wanted one-night stands. They had desires and fetishes. But, as Ilaria explains, the problem is that women are catching up. It’s just that men don’t know it. And don’t like it. Dating has never been trickier.

Now I love Italy and Italians, and refuse to tar an entire nation. But I also once dated an Italian man and have seen the difficulties. I met Fabrizio in 2006 in Turin, where he was a barman and asked me out. I, taken aback (Fabrizio was crazy handsome), agreed. First date: in an erroneous move, I ordered An Alcoholic Drink and Fabrizio informed me that I had a drink problem. Inexplicably, I agreed to a second date. Fabrizio told me I had beautiful eyes and we kissed. On the third date I invited him back to mine. Halfway through a kiss, Fabrizio pulled away and told me he had to go, explaining his mother was expecting him (he was 34), adding: “You English girls are troppo facile’’ (too easy). Ilaria is not surprised at my story. “Mostly they are afraid of sexual women,” she says. This is most obvious in Milan, due in part to the boom of women in high-powered professions. “Milan is the most modern city in Italy.”

We meet her friend Marianna Tognini in Mag Cafè, a popular bar in Navigli, the riverside area that has become a byword for hipsters. This is where the young come to pull. Except no one’s pulling, because in the past two years hipsterdom has confused more traditional Italian notions of masculinity. And, says Marianna, “because of how they look, you don’t know who is gay and who is not, so you don’t know who to approach”.

These two women have a plan to teach me to pull Italian men, so we sit and drink and wait for a couple of hours, completely untroubled by admirers. We’re surrounded by men with beards and tattoos, some wearing leggings under their jeans, which seems to be a trend for men here. We make eyes at guys, but no dice. Ilaria suggests that we abandon Mag and head to checked-tablecloth restaurant Sabbia d’Oro. For a Thursday, it’s busy. Big groups of loud, well-dressed artistic types sharing plates of linguine spill out on to the pavement. The streets teem with übers and fixies. We’re gently hassled by some out-of-towners, but otherwise the men play it very aloof.

Over some pretty exquisite linguine alla vongole, I tell them about my fabulously crap day on Tinder. When I finish my story and await their pity, Marianna rolls her eyes. “Yes, this is all normal,” she says. Tinder seems to mystify Italians. Ilaria says that apparently Italian men on Tinder are three times as likely to swipe left – ie signal their interest – than women. But very few actually follow through with dates. “Italian girls who want strings-free sex are still believed to be in the minority,” she says. Marianna says that Tinder had helped her find sex before, “but mostly in New York; there, you know what you’re getting, there is an understanding. Here...” She wags a finger.

We move to a rum but lively bar called Cape Town on the outskirts of Navigli and order Moscow Mules – “which is what all the kids drink, you go crazy,” laughs Marianna. Outside, we loiter, drink and giggle. The crowd seems young and knowing. For a country which doesn’t encourage extreme drinking, I’m surprised by the number of pissed clientele. But then cocktails, late nights, and nightlife with an edge all make up a growing scene in Milan.

Ilaria gives me some pointers: “Italian men wanna be like Rodolfo Valentino – you are a mountain that they want to climb and win.” I am approached by a preppy young American who has fled Wall Street to work in a vineyard, and I approach another, a charming illustrator. I don’t get anywhere – I guess I don’t float his Milanese boat – but who knows what other factors may be against me. Blogger and activist Edoardo Moreni recently wrote an essay blaming Tinder’s failure in Italy on the statistic that 80% of young Italians still live with their parents. It’s hard to participate in strings-free sex when your mum is downstairs.

I leave Milan wondering if it’s less the men who have changed than the women. Gianni, a barman in my hotel, had said: “The women in Milan are different. They are not like the women I grew up with – my mother, people like that.” Ilaria had laughed when I told her. “Italian women want sex. Boys’ mothers have not taught them this. But as we all know, the mother is the woman they’ll always want.”

ESSENTIALS

Morwenna Ferrier’s flights were provided by British Airways which flies twice daily from Heathrow to Milan, Malpensa from £110 return and seven times a day from Heathrow to Milan, Linate, from £115 return (ba.com/barcelona). Double rooms at the Sheraton Diana Majestic Milan start at £134 (sheratondianamajestic.com).The Leading Hotels of the World offers stays at Palazzo Parigi Milan from £512 per room (lhw.com/palazzoparigi)

For more inside tips, advice and holiday ideas, go to theguardian.com/travel