Flirting is a game: reclaiming the lost art of the chat-up line

two flamingos kissing making love heart shape

‘On an app or in a bar, personalisation is key,’ says relationship coach Kate Mansfield.
Photograph: Kelly Bowden/Getty Images

Oh, don’t get me wrong, I knew it was a line. I was on a date I wasn’t sure I was ready for. Had my life gone to plan, I should have been married by that point and living in a foreign city. But I was sitting opposite a stranger in London, feeling old and unattractive.

“Forty?” he said. “Forty is nothing! You were a girl before. Now you’re at the very beginning of being a woman, no?”

He was French, and the accent certainly helped him get away with it. As did his raised eyebrow, indicating he knew damn well it was a line too.

But, also, I wanted to hear it. Flirting is a game, and I wanted to play again. To have some sparkle in the grim winter. To feel like a woman, no?

I had begun using “the apps”, as everyone referred to them, under the impression that it was the only way people met someone these days. Results were mixed. The phone screen would glow. A notification would appear. Interest would rise. Who could it be, what would they say?


Not even a capital letter. Instant deletion.

“Hey” seeps through the modern dating world like mould through a fruit bowl, a tiny disappointment below the tempting surface. Sixty-eight percent of users surveyed by dating app Inner Circle agree, saying it was lazy, while another 45% said it made them feel as though the sender wasn’t really interested. In response, the app has implemented a feature offering an autofilled chat-up line when it detects a user typing “hey”.

The chat-up line – whether used as an opener or to express interest after some neutral conversation – has a history as long as love itself. They are there in the Song of Solomon (“Thy love is better than wine”), in Midsummer Night’s Dream (“What angel wakes me from my flowery bed?”), but the chat-up line’s true golden period coincided with Hollywood’s golden age.

Although, when it comes to old Hollywood smoothies, we think of Clark Gable (“You should be kissed, and often, and by someone who knows how”) or Humphrey Bogart (“Here’s looking at you kid”), many of the sassiest lines came from female characters. Mae West flew the flag for sexually forward women back in 1933, asking Cary Grant’s character in She Done Him Wrong: “Why don’t you come up sometime and see me?” Then there’s Lauren Bacall in To Have and Have Not, leaving Humphrey Bogart with the promise of more (“Just whistle. You know how to whistle, don’t you, Steve … You just put your lips together and … blow”), or Audrey Hepburn, playing against her wide-eyed type in Charade, saying: “I don’t bite, you know … unless it’s called for.”

But as the decades moved on and cinema’s focus pulled away from adult dramas and screwball comedies to action films and superheroes, film chat-up lines declined along with the number of sharp female roles. James Bond’s winking corniness ruled and so many of Bond’s lines, even with their knowing irony, depend on being delivered by a spy who loved you.

In real life, the chat-up line was devalued even further by the pick-up artist community, which consisted mostly of heterosexual men who would study and share techniques designed to cajole or manipulate women into sleeping with them. Neil Strauss’s 2005 book The Game: Penetrating the Secret Society of Pickup Artists was the tipping point, introducing millions to ideas such as “negging”, a pick-up technique based on undermining a woman’s self-confidence in order to make her seek approval. PUAs (pick-up artists) saw seduction as a formula, women as interchangeable units.

“On an app or in a bar, personalisation is key,” says relationship coach Kate Mansfield. “Read the person’s profile and ask an open question that will invite an answer. In a real-life setting, just introduce yourself and say hi.”

Mansfield isn’t a fan of pre-prepared chat-up lines. “They lack intimacy,” she says. Her most general recommendation is to praise an item of clothing – telling someone you like the colour of their shirt does indicate you think they look good, but also praises their taste and choices.

It should go without saying that any hint of sleaziness should be avoided. And context is everything. It’s very important to know when to back away when coming on. In the context of a dating app, flirting is expected and a well-tailored opener is worth a million heys. They can even be fun, covered in irony and cheese, in the context of a relationship. As I sat down to write this, my phone pinged with a message from my boyfriend.

“You know you have a beautiful face and a sexy body,” it read. “But what don’t you know?”

Slightly confused, I replied: “No idea. What?”

“My phone number!”

“Is this because you knew I was writing about chat-up lines?”

A grinning emoji appeared.

“Thank you for being supportive of my work.”

In the end, support and laughter are what we’re all after. A chat-up line could be the start.

So why not try more than hi? Sign up to Inner Circle, and get one month’s full membership for free


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