Finding someone today is probably more complicated and stressful than it was for previous generations—but you’re also more likely to end up with someone you are really excited about.

This is a book that only Aziz Ansari could write and he does so brilliantly. Teaming up with an academic sociologist (Eric Klinenberg), and using focus groups from reddit and his comedy shows, he explores how dating works in modern times. Specifically, how do we go about looking for love when we are able to live virtually anywhere, and communicate with anyone at any time? This book is more a meditation than a how-to guide, and Aziz is insightful, compelling, and hilarious throughout.

Further Links:
Check out Aziz’s hysterical Madison Square Garden special on Netflix (a couple YouTube bits relevant to this book: Making Plans With Flaky People and Creepy Dudes Are Everywhere).
The Freakonomics podcast that sold me on reading this book.
What the professionals are saying: Vanity Fair’s review.
Quotes and Anecdotes: Stop going on Boring Ass Dates
Buy on Amazon

Highlights

When I started the project, I thought the big changes in romance were obvious—technological developments like smartphones, online dating, and social media sites. As I dug deeper, however, I realized that the transformation of our romantic lives cannot be explained by technology alone; there’s much more to the story. In a very short period of time, the whole culture of finding love and a mate has radically changed. A century ago people would find a decent person who lived in their neighborhood. Their families would meet and, after they decided neither party seemed like a murderer, the couple would get married and have a kid, all by the time they were twenty-two. Today people spend years of their lives on a quest to find the perfect person, a soul mate. The tools we use on this search is different, but what has really changed is our desires and—even more strikingly—the underlying goals of the search itself.

There are no longer any predetermined life paths. Each of us is on our own.

In 2007 the number of texts exchanged in a month outnumbered the number of phone calls made in the United States for the first time in history. And in 2010 people sent 6.1 trillion texts across the planet, roughly 200,000 per minute.

The interesting thing about text is that, as a medium, it separates you from the person you are speaking with, so you can act differently from how you would in person or even on the phone.

As a medium, it’s safe to say, text facilitates flakiness and rudeness and many other personality traits that would not be expressed in a phone call or an in-person interaction.

The fact that your interactions on your phone can have such a profound effect on people’s impression of you as a person makes it clear that you basically have two selves now—your real-world self and your phone self.

These notions about waiting and playing hard to get have been around for ages. According to Greek historian Xenophon, a prostitute once went to Socrates for advice and he told her: “You must prompt them by behaving as a model of propriety, by a show of reluctance to yield, and by holding back until they are as keen as can be; for then the same gifts are much more to the recipient than when they are offered before they are desired.” Conversely, Socrates knew that people tend to discount and sometimes even reject the things that are always available.

Psychologists have conducted hundreds of studies in which they reward lab animals in different ways under differing conditions. One of the most intriguing findings is that “reward uncertainty”—in which, for instance, animals cannot predict whether pushing a lever will get them food—can dramatically increase their interest in getting a reward, while also enhancing their dopamine levels so that they basically feel coked up.

If were honest with ourselves, we realize that, however bizarre, we actually prefer to be lied to. If someone lies and says they are dating someone or they are moving to another town soon, you don’t feel rejected, because it’s no longer about you.

When I’ve really been in love with someone, it’s not because they looked a certain way or liked a certain TV show or a certain cuisine. It’s because when I watched a certain TV show or ate a certain cuisine with them, it was the most fun thing ever.

That’s the best thing about the internet: it doesn’t simply help us find the best thing out there; it has helped to produce the idea that there is a best thing and, if we search hard enough, we can find it. And in turn there are a whole bunch of inferior things that we’d be foolish to choose.

Schwartz’s research, and a considerable amount of scholarship from other social scientists too, shows that when we have more options, we are actually less satisfied and sometimes even have a harder time making a choice at all.

“How many people do you need to see before you know you’ve found the best?” Schwartz asked. “The answer is every damn person there is. How else do you know it’s the best? If you’re looking for the best, this is a recipe for complete misery.

The attitude of these guys was to give people a chance. Instead of sampling a bunch of jams, they had learned how to focus on one jam and make sure they could appreciate it before they walked away.

The more I thought about that approach to dating, the more appealing it became. No matter how many options we have, the real challenge is figuring out how to evaluate them.

Look at my dad: He had an arranged marriage and he seems totally happy. I looked into it and this is not uncommon. People in arranged marriages start off lukewarm, but over time they really invest in each other and in general have more successful relationships. They are more invested in the deep commitment to the relationship, rather than being personally invested in finding a soul mate, which can tend to lead to the “Is there something better out there for me?” mentality.

Do the dates you usually go on line up more with the mundane/boring or the exciting/novel variety? If I look back on my dating life, I wonder how much better I (and the other person) would have fared if I had done something rather than just get a stupid drink at a local bar.

Initially, we are attracted to people by their physical appearance and traits we can quickly recognize. But the things that really make u fall for someone are their deeper, more unique qualities, and usually those only come out during sustained interactions.

There’s something uniquely valuable in everyone, and we’ll be much happier and better off if we invest the time and energy it takes to find it.

But in a similar sense the Tenga seemed to be an alternative to casual dating and sex. It was a way to avoid putting yourself out there and having an actual experience with another person. Say what you will about casual sex and the substance and quality of that experience, but the more casual encounters I had in my own periods of singledom helped me grow as a person and brought me to a place to be ready to have a serious relationship. It also made me realize the true value of that sort of connection and better understand the advantages and disadvantages of a serious relationship. Dating has its downsides, but it can be a lot of fun. Even when it isn’t, when you’re meeting other people there are always experiences that you remember and learn from.

If you live a responsible life, you’ll run into responsible people.

Anthropologist Helen Fisher, the author of Anatomy of Love and one of the most cited scholars in the study of sex and attraction, was part of a research team that gathered and took brain scans of then-middle-aged people who’d been married an average of twenty-one years while they looked at a photograph of their spouse, and compared them with brain scans of younger people looking at their new partners. What they discovered, she writes, is that: “Among the older lovers, brain regions associated with anxiety were no longer active; instead, there was activity in the areas associated with calmness.” Neurologically it’s similar to the kind of love you feel for an old friend or a family member.

In the United States, sociologist Andrew Cherlin writes, “marriage has become a status symbol—a highly regarded marker of a successful personal life.”

The “good-enough marriage” is definitely not good enough for today’s singles. We’re not content to marry someone who happens to live down the street anf gets along okay with our parents.

As we see more and more people online, it can get difficult to remember that behind every text message, OkCupid profile, and Tinder picture there’s an actual living, breathing, complex person, just like you.

But it’s so, so important to remember this.

For one thing, when you forget you’re talking to a real person, you might start saying the kinds of things in a text message that no person in their right mind would ever say to a real-life person in a million years.

If you were in a bar, would you ever go up to a guy or girl and repeat the word “hey” ten times in a row without getting a response? Would you ever go up to a woman you met two minutes ago and beg her to show you one of her boobs? Even if you are just looking for a casual hookup, do you really think this will work? And if so, do you really want to bone someone who responds to this?

Online dating works best as a forum where you can meet people whom you’d never otherwise be able to meet. It’s the ultimate way to expand the search beyond the neighborhood.

Sure, there were lots of people in previous generations who met someone in the neighborhood and grew up to have a deep, loving soul mate-level bond. But there are many others who didn’t. And the current generation won’t take that risk. We want a soul mate. And we are willing to look very far, for a very long time, to find one.

A soulmate isn’t just someone we love. As for our grandparents, there are probably lots of people out there whom we could settle down with and, in the fullness of time, grow to love. But we want more than love. We want a lifelong wingman/wingwoman who completes us and can handle the truth, to mix metaphors from three different Tom Cruise movies. 

Historically, were at a unique moment. No one has ever been presented with more options in romance and expected to make a decision where the expectations are so astronomically high. And with all these choices, how can anyone possibly be sure that they’ve made the right one?

Get over it: You can’t! So you just have to power through and have hope that as you grow and mature, you’ll eventually learn to navigate this new romantic world and find someone who does feel right for you.