Men who ask women on dinner dates deserve to fail.

"It's just so cliche," says Rupert. "It puts so much pressure on things, having to sit there and try to talk to somebody you don't know, stuffing your face, with your best table manners, and then it's 'who pays' and it's awkward. It's the worst game."

Rupert has game. Rupert has two girlfriends, but only one knows about the other. On a slow week, Rupert (no, that is not his real name) has sex with an additional two or three women.

He used to be jealous of his gay friends who scored on the hook-up app Grindr. Then along came Tinder. At first, he says, Kiwi women thought Tinder was a dating app, a digital path to True Love and The One.


Now: "No shit, you can chat to a girl on Tinder and she will come over, probably within two days, without ever having met you, she'll come over to your apartment and bring a good bottle of pinot and stay that night. It has become even better than Grindr because they provide the wine. If you want to, you can actually do that. And I could probably do that five nights a week."

Rupert, a 41-year-old company director, has just got up to shut his office door.

On the other end of the phone, I am processing what he has just said.

Me: "How can you say that out loud and not realise you sound like a complete pig?"

Him: "There are a whole lot of people out there going 'that's what I want to do'. They're not being manipulated into that situation. It's just free will. It's females making their own choices in life. It's not always about guys being bad. A lot of the sexual revolution that's going on is about female empowerment and liberation and them doing what the hell they want, and why the f*** not? Gays can do it, we can do it, anyone can do it. It's great."

This is what it is like to date in 2018. Photo / Getty Images
This is what it is like to date in 2018. Photo / Getty Images

It is just five months since American film producer Harvey Weinstein was publicly accused of sexually abusing dozens of women over a period of at least three decades. The story, broken by the New York Times and The New Yorker, drove the creation of the #MeToo social media campaign and the Time's Up movement. Since then, thousands of women worldwide have shared stories about the sexual misconduct of men.

The story you are reading started life as a look at flirting in this post-Weinstein world. Today, phrases like "toxic masculinity" and "consent is sexy" dominate the lifestyle section of any given news cycle. Lisa Bonos, writing for the Washington Post, recently gave a typical analysis: "This is what it is like to date in 2018. Plenty of heterosexual men are confused about how to make the first move in a way that is confident and mindful of a woman's boundaries."

So, when I approached women to talk about contemporary flirting, I expected them to say yes, they felt more empowered. And I expected men to say yes, they were thinking harder about their behaviour. What I didn't expect was this: "This one guy, I thought I'd have some casual sex with him. I thought, I'll just go over and we'll have a weekend and see how it goes, and he just became . . . well, he was in LOVE. He thought it was all on. He became HORRIBLE," says Carole, 49.


Or this: "I'm just friendly. I like women. But I haven't got a clue. A woman could be standing in front of me naked . . . and I would be like [adopts tone of dawning recognition], 'oh — you want to f***?'" says John, 45.

When I asked for stories about flirting, what I didn't expect was the frank-funny-horrifying-terrifying-sweet-sad spectrum of experiences that define dating in the modern world.

Only one subject let me use his real name. James Mustapic is a 22-year-old stand-up comedian who popped up in my Twitter feed when he wrote this: "When ur flirting with a boy on Snapchat and realise their bitmoji looks the exact same as u . . ."

And there they were. Two clean-cut, white boys who could have been twins if they weren't cartoon avatars (or "bitmojis") who might, or might not, have real-life sex some time.

"I don't think I'm that good at flirting in real life," confesses Mustapic.

"Maybe because I've never really had to that much. I try my best, but I don't have as many set methods, whereas I guess when I'm online sometimes I have a few more."

James Mustapic. Photo / Jason Oxenham
James Mustapic. Photo / Jason Oxenham

The internet was conceived in the early 1980s. By 1990, the World Wide Web had become a thing. Mustapic, born six years later, has never lived in a time when humans weren't online. Once upon a time, humans wore their Saturday best and signed each other's dance cards in country halls. Today they just need a smartphone.

The Oxford Dictionary has described emoji — the small digital icons you stick on a text message for emotive emphasis — as a "nuanced form of expression" that transcends language barriers.

You've probably signed a text with a heart or a smiley face. But if you're new to digital flirting, beware — an aubergine does not mean moussaka for dinner and not everyone who sends spurting teardrops is sad.

"I read this thing that said people who use emojis have more sex," says Mustapic.


"I think there's something in it. I like ones that aren't too overt. The kissy face, and the kind of cheeky ones. I've had someone use the dragon to represent their penis."

That seems . . . confident?

"It's one step further than the eggplant!"

Mustapic says he's had some creepy experiences ("they're usually older men") but, he says, nothing like he has seen reported in the heterosexual world.

"I don't want to be like 'oh, a gay man has the same struggle as a woman'. Women often have a lot less power than men . . . I guess in the gay world, it is a wee bit different because with two guys, or two women — that sort of stuff still happens everywhere, but I think it is maybe a wee bit less."

And, says the man whose Auckland Comedy Festival show will be called Mildly Wild, "I haven't noticed a decrease in flirting!"

What, exactly, is flirting? And why do we do it? Psychologists draw comparisons with the animal world, where behavioural displays are used to attract potential mates. But what do you do when you don't have a peacock's plumage?

I ask Rupert for his best lines, and he just laughs.

"You just start a conversation. But you start conversations as though they've been going for ages. It's called the use of threads. You create a thread and then you start conversing on that thread and when you meet in person, you can immediately pick up on those threads and build comfort."

That shift to online flirting, he says, is partly about safety — you can assess, before you meet, whether an attraction is mutual.

"The days of going out and hoping for the best are long gone. There is more of a risk. I've never wanted to get anywhere close to that line. I'm not in those situations where people are drunk, for example, because I stay away from Ponsonby Rd on a Saturday at 2am. I would be very, very cautious of that. But I've been in the game a long time. I know what the hell I'm doing."


Carole (of the sex-not-love weekend) says in her experience, men are "really f***ing confused".

She describes herself as smart, attractive and successful. "But I am very cautious about who I flirt with, because the minute you start, boys think 'yep, I'm in'. I'm very outgoing and I think that can be misconstrued as flirting."

Sarah, 32, says she's not a flirt — she simply finds it easy to talk to people, and on a date, "I like to have a bit of flirting in the conversation, otherwise it gets boring . . . but there are men who don't seem to know how to flirt without being creepy."

Exhibit A: "I was not into it at all and then right at the end, we were at the pub and I was trying to think of an excuse to get out of there and he said, 'do you mind if I have a cigarette?' He had yellow smokers' teeth, and then he goes 'I'm going to give you a big smoky kiss at the end of this date'."

Sarah declined. And that's when her date leaned in and said: "You know what I like about you? Your mouth says one thing, but your eyes are telling me a completely different story."

How bad does it get on the flirting frontline?

Louise, 30, was at the very drunk end of a long night in Ponsonby when she went to get food with a friend. A guy sits beside the two women and asks Louise for a bite of her burger. She says yes. He asks for her number. She says no. Then she and her friend get in a cab. As they pull up at her friend's house, two things happen: Louise realises she has lost her phone and the guy from the burger bar is pulling up in a second cab. Things are blurry. Louise doesn't question why he has followed her and her friend, and a few minutes later, she's in a cab with Burger Guy, en route to her own house. Louise tells the driver: "Don't let this man out of this cab."

She goes into her house. There is a knock on the door. She opens it, and Burger Guy lunges for a kiss. Louise pushes him outside, locks all the doors and windows and listens to him wandering around outside for a while. Louise does not call the police.

"I was drunk and stupid . . . It was a bunch of really stupid decisions on my part. When I tell the story, it sounds horrible."

She imagines the court of public opinion: "Nothing happened. Were you asking for it? You got in the taxi with him."

Louise describes herself as friendly.

"And some guys misconstrue that. But it was just a bite of a burger. I wasn't taking my pants off."

Humans were born to flirt, says Caroline Cranshaw, relationship coach and hypnotherapist.

"Babies flirt. Flirting is just a way of showing approval, that you kind of like somebody or you feel safe with them. Flirting is just enthusiastic self-love that kind of radiates from you, and if you're in the company of people you approve of, you allow that to overflow to others."

But, she says, the tide is turning.

"You have to be careful with it. With everything that is happening with the Me Too and Time's Up movements, both men and women need to be a lot more careful and find out when it's appropriate and when it's not."

Inappropriate flirting, says Cranshaw, is when you objectify a person.

"Treating them as an object, or commenting on them sexually — that's not okay, unless your clothes are off. Both of your clothes!"

Cranshaw says there is evidence men are increasingly nervous about flirting. Photo / Getty Images
Cranshaw says there is evidence men are increasingly nervous about flirting. Photo / Getty Images

Also not okay: Innuendo without mutual attraction.

"That's where a lot of men go wrong," she says. "They push the limit. But if a woman is not responding to you, she doesn't like you.

It's very simple. It's not that we're playing hard to get, or that we need to be convinced.

"Women are really clear about whether they like someone or not. And if she's saying she's not interested, she's turning away — get the hint."

Cranshaw says there is evidence men are increasingly nervous about flirting.

"I've definitely had men complain about that — that they can't even say 'you look nice today' because anything like that is construed as sexual harassment. And that kind of sucks, but it is just the way it is at the moment, and they just need to get over it. Women are sick and tired of having been harassed their whole lives, and that's been okay, and if you ever complain about it, you're just imagining things, or you're just being a bitch.

"Men are kind of pissed off about it, I think. But you know what? Women have been pissed off for our whole fricking lives. So welcome — how does it feel?"

American-born Cranshaw says Kiwis are generally "terrible" at dating and flirting. She's about to launch a new matchmaking service that will include advice about flirting successfully — and safely.

"I think it's learning to be open. Open with your body language, open to conversation, and not having any attachment to the outcome," she says. "Flirting is about fun and connecting and letting that light within you shine on someone else."

Best advice for modern daters? "Keep it clean. No dick pics. Gauge the other person. If they're not showing interest, move on. Very quickly!"

And that guy who thinks a woman's eyes are saying something different to her mouth? "Listen to the mouth!"