The best books on Dating

As the author of The Future of Seduction, you’ve agreed to recommend five of the best books on dating. What brought you to this subject originally?

The book was born out of my personal experience. I met my ex-husband in New York, when Sex and the City was in full swing, and we had quite a traditional courtship. I got divorced just as Tinder was launching in the UK, and the game had become utterly unrecognisable. There were no rules, it seemed. I set out to research what had changed—for myself at first, but I quickly realised that there were bigger societal issues at play.

I think one of the problems with dating is that it’s so personal, you know? If you find it difficult, you blame yourself; you think you’re doing something wrong, or that there’s something wrong with you. But 67% of daters, according to the last Pew survey, were dissatisfied with their dating life, and 75% were finding it hard to meet people, which is extraordinary given the seeming sexual smorgasbord available on dating apps. As I dug into the data, I thought it was important to get the message out so that people could contextualise their experience within a broader picture.

Then, while I was researching, #MeToo exploded. What started as sharing stories about harassment and assault detonated into a broader conversation about consent and gender dynamics. So for me, those elements became really interesting to investigate.

In one of my favourite novels, The Love Affairs of Nathaniel P. by Adelle Waldman, one character argues that dating is not discussed with sufficient seriousness: “It is probably the most fraught human interaction there is,” she says. “You’re sizing people up to see if they’re worth your time and attention, and they’re doing the same to you … We submit ourselves to intimate inspections and simultaneously inflict them on others.” 

When Kristen Roupenian’s short story ‘Cat Person’ went viral at the end of 2017 after appearing in the New Yorker, one of the reasons it was so widely shared was that many millennials said that they rarely saw the pitfalls of getting to know someone over text taken seriously.

We’ve experienced a sea change in habits and behaviour—the tools we use to meet and mate have evolved more in the past ten years than in the previous 10,000. And yet, because it affects mostly young people, dating traditionally gets relegated into the territory of glossy magazines. In light of the high quality of content in many women’s magazines now, that isn’t in and of itself dismissive. But given how many books have been devoted to how technology is affecting cognition, democracy, and other elements of our lives, I thought its effects on intimacy merited an in-depth consideration.

To Waldman’s point about ‘intimate inspections’, the price we pay for having more options to swipe through and dismiss is that we, too, invariably become an option to be swiped through and dismissed.

Some background reading, first, before we come to the problems of the present. The first book you want to recommend is the Ars Amatoria, by Ovid, often translated as The Art of Love.

This is the first known seduction manual. It was published around 1 or 2 AD. It consists of three books—two for men and one for women—about where to find women and how to win them over, and similarly how to find and keep men. It’s comforting to know that people have had the same concerns for millennia.

As well as being the oldest seduction manual, it’s probably the world’s longest banned book. It is thought to have contributed to Ovid’s exile on allegations of immorality in 8 AD; it was thrown on the Bonfire of the Vanities in Florence in 1497; it was banned in England in Elizabethan times and believe it or not, seized by US Customs on the grounds of obscenity as recently as 1930.

“Playing hard-to-get does have a physiological basis, drawing on the dopamine hit of variable rewards”

The remarkable thing is how contemporary the advice reads. There are a few lines that are problematic from a modern perspective about forcing women, but scholars differ on how seriously to take them given Ovid’s style and the text that follows. In any case, as Mary Beard has said: you’re not going to find gender equality in ancient Rome, and the book for women indicates an understanding of their sexual agency, which is in and of itself revolutionary.

Ovid offers grooming advice for men (“Do not let your nails project, and let them be free of dirt; nor let any hair be in the hollow of your nostrils…”) He recommends giving women compliments and not asking their age, and he talks about the pleasures of mutual orgasm. The section for women could be straight out of Cosmopolitan—covering hair, make-up, how to dress to impress… And again, it’s rather provocative because he suggests sex positions; tall women, for example, are advised against straddling their lovers.

It’s pretty bawdy, then.

That’s why people are not sure how seriously to take the questionable passages. Ovid is quite tongue-in-cheek.

He counsels playing hard-to-get for both men and women to increase interest, as almost every how-to dating manual has done since. So playing hard-to-get to stoke interest is one of the oldest tools in the box.

Yes, let’s talk about dating manuals briefly. You’ve not selected classic bestsellers like The Game or The Rules, but I’d still like to discuss them because they are such a perennial feature of bestseller lists, or at least they were until quite recently. Obviously there’s a lot of interest in them. But can books really teach us how to be more successful in dating?

The attraction of manuals is that we want an element of control in an area of our lives that’s not entirely in our hands, both in terms of the serendipity of encounters and whether our feelings are reciprocated. The uncertainty is what makes it exciting, but also causes us difficulty, and makes it an emotional rollercoaster. So we love to think that there might be a set of rules that we can play by to achieve what we want.

Or even cheat codes, which I think is what The Game claims to offer: psychological tricks to make yourself appear more attractive.

As painful as it is to be on the receiving end of the strategy, hard-to-get does have a physiological basis, drawing on the dopamine hit of variable rewards. Research shows that while we want to be wanted, we’re attracted to uncertainty even more. All addictive internet technology, including dating apps, is designed to exploit that human vulnerability.

However, the fundamental problem—and, I think, why we haven’t seen a dating manual in the past decade sell as many copies as The Rules did in its day—is that for hard-to-get to work, you need to be seen as a prize rather than just a commodity. With the abundance of options on apps, it’s very difficult to make yourself appear unique, when there are hundreds of people who seem just like you on the same app. If you try to make yourself seem scarce, the person on the other side of the screen will just move on to the next quasi-indistinguishable profile.

So the proliferation of dating apps have brought the death of the dating manual?

Well, listen, people will always try to game it, or pretend it’s possible to game it for profit. There’s certainly no shortage of seminars and online forums to discuss this stuff. Although pick-up artistry has fallen out of public favour, its playbook, The Game, remains in print, and there is a huge industry of pick-up artists, or PUAs, who have rebranded themselves as ‘seduction coaches’ teaching techniques including ‘overcoming last-minute resistance’.

Let’s back up a little, and talk about how we got to this point. The second dating book on your list is Beth Bailey’s From Front Porch to Back Seat: Courtship in the 20th Century. It’s a history of social mores in the United States.

That’s right. Bailey details the move from ‘calling’ to ‘dating’, and what that meant in terms of gender relations. She argues that calling—which took place in a woman’s parlour—kept courtship in her domain of control. A woman, or her family, would invite a man to come call, and it was considered rude to arrive without an invitation.

The conventions of courtship were replaced by dating as people moved to cities to work in the early part of the 20th century. Lower class working women didn’t have parlours in which to receive men, and so dating became about going out to do something. Envious of the freedom afforded by unchaperoned encounters, women from the upper classes came to adopt the practice as well, and the advent of cars spread dating outside of cities.

“The word ‘dating’ was first used by prostitutes to refer to their appointments”

Bailey is unequivocal that this fundamentally altered the gender dynamic, because the man was expected to pay for a date —at the time, men out-earned women two to one, so there was no question of going Dutch. As he did the inviting, and the paying, it gave him control.

It also introduced this economic element of dating, whereby women were expected to offer sexual favours in exchange for a date. Interestingly, the word ‘dating’ was first used by prostitutes to refer to their appointments. So it maintained that economic connotation, even when it fell into popular usage.

I had no idea. I’m quite shocked, actually. It’s very telling, I suppose, how much discussion still goes into that question of whether or not a man should pay for dinner, and what you might owe him if he does.

Indeed. The other interesting thing is that, whereas Ovid is reassuring in that our central concerns have stayed the same—how do you attract someone, and how do you keep them—Bailey shows how much conventions can change from generation to generation.

For example, before the war, people didn’t really ‘go steady’; you were supposed to generate what she calls a ‘promiscuous popularity’ by dancing with as many men as you could, and be seen to be dating as many people as possible. Of course, you were not supposed to be sleeping with any of them, but perceived popularity was the main goal.

Then, after the war, when there was an actual man shortage, and because people were drawn to security and safety, couples would start going steady—being serially monogamous—often from a very young age. You would think that parents would be thrilled by this, but because they themselves had benefited from the ‘rating and dating’ system before, they were in fact up in arms that their children were going steady, partly because they thought that with fewer partners there was more risk of premarital sex.

Bailey cautions against nostalgia, of thinking that any problems we have could be fixed by going back to a previous time, because people tend to look back favourably upon their own youth. I certainly had to think a lot about that: how much of my questioning of current practices was because I had grown up with something different? But I think the stats bear me out. Even the youngest demographic, who have not known anything different, are disappointed by the current state of seduction.

It’s a good point, though. Don’t dating apps, and the expectation that you might be chatting and scheduling meetings with dozens of people at once, bring us back to that concept of popular promiscuity?

Well, part of the problem is that different people are looking for very different things from these apps. And many people don’t necessarily know what they’re looking for. I wouldn’t have a moral problem with a new era of free love, if people were using them to hook up. But I do think that it’s problematic that people use the apps so much for ego-boosting procrastination. One study showed that 44% of people on Tinder were not there to meet anybody, either for a relationship or for casual sex. They were just on it to pass the time, as dating apps are deliberately designed with gaming features. Like social media, it’s another example of tech companies developing products for profit: their objective is to hijack our attention, impeding rather than fostering connection.

Maybe this brings us to Christian Rudder’s Dataclysm: What Our Online Lives Tell Us About Our Offline Selves. I assume it grew out of his very interesting data blog OkTrends, which analysed—among other things—the most successful conversation starters on dating sites, and age preferences among women and men.

Yes. Rudder is a mathematician and one of the co-founders of the dating site OkCupid. His book looks at what we can learn about human behaviour from analysing OkCupid data, as well as Big Data on social networks more broadly. Like his blog, it is full of graphs and charts that appeal to my inner math geek. For my purposes, the dating bits were the most fascinating, although sometimes disturbing. He looks at racial bias in people’s sexual preferences. He looks at age bias: a woman is most attractive to men of all ages in her early twenties, statistically speaking, so of course anyone over the age of 24 is not going to be thrilled to read that. That said, young women with the highest erotic capital, as it were, aren’t necessarily enjoying apps due to the paradox of choice.

When you look at the evolution of matching algorithms, a lot of time was invested by traditional dating platforms in trying to predict compatibility. Most sites began by matching people based on their stated preferences, then eventually adjusted the algorithms for their revealed preferences, what they actually choose. Because it was searchable, people would put out criteria that were very specific. You know: ‘I want a non-smoker, who’s a Democrat…’ yada yada. But it turned out that the big issues you would think would predict compatibility—things like religion, politics—turned out not to matter. The three most predictive questions OkCupid found were indicators of a penchant for adventure: ‘Do you like scary movies?’, ‘Have you ever travelled alone?’ and ‘Would you like to ditch it all and go live on a sail boat?’

“So we have built our entire system on a criterion that ends up being unimportant”

Apps essentially threw in the towel on matching based on preferences, letting users pick for themselves, almost exclusively on the basis of looks: 90% of people will swipe left or right based on the first photo. So we’ve been moving towards this system in which looks are the only selection criterion. But it turns out that looks matter far less than we think. Rudder recounts an experiment in which OkCupid sent 10,000 people on blind dates in 2013. Couples were paired randomly: you could be matched with anyone from a ‘1’ to a ‘10’, in terms of attractiveness. While the messaging activity on the site is quite linear—more attractive people get more responses—it turned out that once people sat down in person, looks had no impact on whether or not they had a good time. Women had a good time 75% of the time and men had a good time 85% of the time, regardless of relative attractiveness. So we have built our entire system—pretty much, now that other ways of meeting are getting harder and harder—on a criterion that ends up being unimportant. Which is insane when you think about it.

It’s been a long time since I used a dating app; I’m in a long-term relationship. But I do remember from my brief period on Tinder that when I actually met people, I often found an uncanny mismatch between the person in front of me and the person I had imagined them to be. I suppose what I’m getting at is that it’s very difficult to comprehend the reality of a person from, say, five pictures and fifty words.

Absolutely. There’s no accounting for chemistry from a picture. There is just so much more that can make someone attractive in person, from charm to humour to kindness.

One thing that I learned from the cyberpsychologists I interviewed that I found disturbing is that texting can create a false sense of intimacy. In the absence of in-person cues, we tend to overshare to make up for what’s missing (thus sexting and the ubiquity of nudes). This ‘escalation effect’ can lead to disappointment when you end up meeting, or even be downright dangerous. The National Crime Agency reported a sixfold increase in first-date sexual assaults over five years, a spike they attribute to the growth of dating apps. Forty-one per cent of these assaults happened on first dates that started in a residence. So people are meeting strangers for the first time in their homes. At the beginning of online dating, people were very aware of stranger danger, but that caution seems to have gone out the window.

Let’s move onto our next book on dating, which is Aziz Ansari’s Modern Romance. Tell me why you chose it. I should note that a few people might be hesitant to pick it up, because I know that the writer was the focus of some controversy when he was accused of sexual misconduct in 2018—something that prompted a lot of debate regarding the grey areas around consent.

Yes, those allegations definitely cast a shadow over the good-guy image Ansari had carefully cultivated—both in his public persona and in the book. Nonetheless, I think this book is the one that best expresses to somebody who hasn’t experienced it what it’s like to online date. It was written just as apps were taking off. He shares things like the litany of ‘hey’s that you get and the very sexually aggressive first messages. It’s quite visual, showing actual text exchanges and people’s pouty profile pictures. So I think that really helps communicate what it’s like to participate in this.

The book was co-written with the sociologist Eric Klinenberg. They interviewed Barry Schwartz, the author of The Paradox of Choice, who is quite funny about what it means for dating. In his book, Schwartz explains the psychological effects of having too many blue jeans to choose from, or too many mutual funds or breakfast cereals. As applied to a partner, he says: ‘How many people do you need to see before you know you’ve found the best? The answer is every damn person there is.’ He concludes that ‘this a recipe for complete misery.’ But the apps are built on the illusion that the more choice we have, the better chance of a good outcome, and the happier we’ll be.

“Don’t double text: if you haven’t heard back from somebody, leave it”

I should caveat this, however. For individuals in what’s called ‘thin markets’—with specific sexual interests, for example, or for members of the LGBTQ community—satisfaction rates are consistently higher with internet dating and with apps. Even though they’re plagued with the same issues of racial bias and aggressive messages, the greater choice afforded by apps offers more utility in smaller ponds.

You asked whether there were any useful dating manuals. Modern Romance offers some texting advice. It may seem like common-sense, but sometimes when you’re really interested in somebody, it’s helpful to be reminded not to text back immediately. The Rules has very prescriptive text-back times, which is ridiculous, but it’s true that you don’t want to seem overly eager. (Unless you’re in the middle of a text conversation or sexting, in which case you don’t want to wait half an hour between messages!) Also, don’t double text: if you haven’t heard back from somebody, leave it. The length of texts you send should be about equal or less—you shouldn’t be responding with a paragraph to a text of three words. And the last person who texts in a conversation wins.

I do really strongly remember that sense of ‘winning’ or ‘losing’. While dating, one can be painfully aware of how quickly the balance of power can shift between two people.

Yes. In my day job as a literary critic, I’ve covered a lot of books about consent. I think what’s interesting is that it’s fiction that has been most adept at handling the subject, because it can slow down a scene enough to show the moment where that power switches. We mentioned ‘Cat Person’—that was better able to encapsulate the dynamic between a young woman and an older guy than nonfiction.

The book I’m thinking of is Mary Gaitskill’s This is Pleasure, which absolutely floored me. It was so complex in its moral ambiguity. I think it was the best thing I read about #MeToo.

Exactly. Gaitskill is also an accomplished essayist, but she said she chose to explore the complexities of #MeToo in a novella because fiction gave her more bandwidth for nuance.

Well, perhaps this brings us to your final dating book recommendation: Nichi Hodgson’s The Curious History of Dating: From Jane Austen to Tinder. If Bailey’s book was about courtship in the US, this gives a more British take, is that right?

Yes. She starts in Victorian times with the popularity of lonely hearts ads, which were then imported by the United States, along with calling. And I guess dating, as a convention, was later exported to the UK from the US. Apps have really globalised the American concept of dating, except with a lot less effort put in than might have been done in the past.

Hodgson is much more LGBTQ inclusive than most books of the genre, which I admire because I suspect it involved quite a bit of research. She integrates queer history in a seamless way; it’s not just globbed on as you sometimes get in other books. Mediated dating has always been, by necessity, pioneered by the queer community, from the time of lonely hearts listings. LGBTQ users were the biggest community on Match.com before it got mainstream acceptance and then of course Grindr preceded Tinder as a location-based app.

So, as I mentioned, Hodgson starts with lonely hearts adverts, which were very popular right up until there was a murder in 1828, in which a man killed a 20-year-old woman he’d met through the ads. That put a stop to it for all but the most desperate. Among the upper classes, balls were the main way to meet people the traditional way, although you couldn’t just walk up and talk to somebody, you had to be formally introduced. She shares some fascinating tidbits on ‘fanology’, which is how you indicated interest with the position of your fan—maybe swiping comes from that! She writes about the conventions of calling cards and Valentines, and that for Victorians—I never knew this— the pearl was a symbol for the clitoris. People with a predilection for kink found one another through advice columns in magazines, sharing tips for bondage techniques under the guise of talking about corsetry.

Hodgson follows dating trends all the way up to apps. While marriage rates are down, Hodgson is quite positive about the health of dating. Having experienced it more recently, I am less convinced, and I think the statistics bear this out. A study out of Stanford showed that 80% of singles surveyed had not been on a single date or hooked up in the previous year, which is quite astonishing. And that was before the pandemic! So you wonder what happens when we come out of Covid, having gotten so used to living our lives on screens.

I think that brings us back to your own book. What is the future of seduction?

Despite my disappointment with the current landscape, I am cautiously optimistic. There’s a growing awareness of the downsides of smartphone usage more broadly, so I think it’s possible that Big Tech eventually goes the way of Big Tobacco, with smartphones becoming unsexy, like cigarettes.

If we’ve learned anything from social distancing measures, it’s how much human beings need touch. In the same way that one can be hopeful that we reconsider social care, health care, the environment, and everything else the pandemic has caused us to question, my hope is that people will look inwards and say, ‘You know what? I don’t want to spend my one wild and precious life swiping.’ As it becomes safe to go out again, we can take a page from Ovid and gather the courage to strike up conversations IRL. Love, he wrote, “is no assignment for cowards.”