فصل 02

CHAPTER 2

THE INITIAL ASK

Asking someone out on a date is a simple task that frequently becomes a terrifying conundrum of fear, self-doubt, and anxiety. It’s full of tough decisions: How do I ask? In person? Phone call? Text? What do I say? Could this person be the person I end up spending the rest of my life with? What if this is the only person for me? What if I fuck it all up with the wrong message?

Though technology has added a few new, modern quirks to this dilemma, asking a new person to go on a romantic outing has never been easy. It means declaring your attraction to someone and putting yourself out there in a huge way, while risking the brutal possibility of rejection—or, in the modern era, even an unexplained, icy-cold silence.

For the modern dater the first decision is picking the medium to use: call or text. Some people even throw e-mail or social media messaging into the mix. Just a generation ago the landline or even a newspaper classified ad would have been a first stop to finding romance. Today, though, we look at our screens almost immediately. In fact, for many daters a large chunk of their romantic world lives in their phone world.

A quick note: The numbers show that men are still overwhelmingly the ones expected to initiate the first ask. In 2012 only 12 percent of American women had asked anyone out in the previous year. So when discussing this, I use the situation of a guy asking a girl out. The issues discussed generally translate both ways (minus the issue of girls hating dudes initiating with penis photos).

All right, let’s see what the overall trends are.

In 2013 the Match.com survey researchers asked Americans: “If you were asking someone out on a first date, which method of communication would you be most likely to use to get in contact?” Here’s what they found:

Two things to note here. First, the drop in phone calls as a preferred method when you change age groups (52 percent to 23 percent) is stark. Among teenagers the percentage who use text messaging is even higher. In a 2012 textPlus survey, 58 percent of Americans between ages thirteen and seventeen said they’d ask someone out with a text message.1 It’s clear that younger people, who are growing up in a more text-heavy culture, are much more comfortable living their romantic lives via text.

Second, over time, so are all of us.

In 2010 only 10 percent of young adults used texts to ask someone out for the first time, compared with 32 percent in 2013. Asking out someone via text is on course to be the new norm: The phone call is quickly being phased out.

It’s worth pausing here to note that this is an insanely fast transformation in how we communicate. For many generations young people used telephone calls to reach out to possible romantic partners. It was a harrowing experience that we all could relate to. Before the initial ask, you would hear terrifying rings and then an answer. It could be the object of your desire or a roommate or even a parent. At that point you would ask to speak with the person you wanted to ask out.

If they were around, the person would finally say, “Hello,” and a mild panic would ensue. You would have to spend some time chatting them up, trying to form a bond while also setting things up for a possibly awkward segue into a date ask.

“Hey, so yeah, anyway, I lost the pie-eating contest . . . You wanna see a movie sometime?”

This phone-call ask required some bravery to initiate and some skills to execute properly, but over time you’d get better at it and you would strategize these calls.

Let’s say you were a young man named Darren. At first, your calls might be something like this:

DARREN: Hey, Stephanie. It’s me . . . Darren.

STEPHANIE: Hey, Darren, how are you?

DARREN: I’m good.

DARREN: [long pause]

DARREN: Okay . . . Bye.

But soon you’d get better. With time, you’d realize how to be confident on these kinds of calls. You’d have a funny anecdote or conversation piece ready. Witty banter would be at the tip of your tongue, and soon you and Stephanie would be two verbal fencers parrying and riposting it up like this:

DARREN: Hey, Stephanie. It’s me, Darren! [confident, energetic]

WOMAN: Hey, Darren. This is Stephanie’s mom. One second . . .

DARREN: Shit. [quiet]

DARREN: You got this, Darren. You got this. [quiet]

STEPHANIE: Hello?

DARREN: Hey, Stephanie. It’s me, Darren! [back to confident, energetic]

STEPHANIE: Oh, hey, Darren. What’s up?

DARREN: I just got an umbrella!

STEPHANIE: Cool . . .

DARREN: All right, bye!

• • •

Well. You’d get better than that.

The skill that went into making a phone call to a romantic interest is one that younger generations may never need or want to build.

As our technology becomes more prevalent in our lives, romantic behavior that seems strange or inappropriate to one generation can become the norm for people in the next one.

For instance, in a recent survey 67 percent of teens said they’d accept an invitation to prom by text.2 For older generations the idea of getting invited to something as special as prom by a text message may sound cold and impersonal. It seems inappropriate for the occasion. But younger folks live in a text-heavy environment and this shapes their perception of what is appropriate. For example, in a topic we’ll revisit in more depth later, breaking up with someone via text seems pretty brutal to people of my generation, but when we interviewed younger people, several said their breakups happened exclusively by text. For younger generations, who knows what texts lie ahead?

THE RISE OF THE TEXT MESSAGE

Texting, otherwise known as Short Message Service (SMS), was thought up by Friedhelm Hillebrand, a German engineer, in 1984 and achieved for the first time by Neil Papworth, a young British engineer who messaged his friend “Merry Christmas” in 1992. Alas, his friend didn’t reply, because his mobile phone didn’t allow him to input text.3

Sure it didn’t. That’s the same shit I hear from friends who don’t respond to my mass “Merry Christmas” text. I even throw in a custom image every year; peep this one from 2012.

That said, can you imagine how insane that must have been—to get the first text of all time? When no one knew what a text was? It would have been like “WHY ARE THERE WORDS ON MY PHONE??? PHONES ARE FOR NUMBERS!!”

In 1997 Nokia introduced a mobile phone with a separate keyboard, setting things up for the BlackBerry epidemic that would soon afflict most of the global yuppie community, but it wasn’t until 1999 that text messages could cross from one phone network to another, and after that usage began to rise. 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.

Technology companies have introduced all kinds of new services to help us exchange short messages, and we’ve responded by tapping away like never before. And of course, this has translated to a vast increase in the number of romantic interactions that are being carried out over text.

One reason for the spike in asking people out by text is that far more of us have smartphones with big screens that make messaging fun and easy. According to consumer surveys, the portion of all American adults who owned a smartphone went from 17 percent in 2010 to 58 percent in 2014, and they’re most prevalent among those emerging adults between ages eighteen and twenty-nine, 83 percent of whom carry a smartphone wherever they go.4 When we’re not doing traditional texting, we now have apps like WhatsApp, Facebook Messenger, iMessage, and direct messaging on Twitter, which allow us to message for free. Throughout the world a growing number of people are using SMS for basic communications, and young people in particular have adopted texting at the expense of old-fashioned phone calls.

That said, we haven’t given up our old habits altogether. Many people, including young adults, enjoy an occasional phone call and even think that it can signal something special in a budding relationship. But when we first started talking to people about how they ask one another out, we learned that with all these technological transitions, our feelings about when to use which medium have gotten pretty mixed up and confused. How do we figure out when to call, when to text, and when to just drop everything, stand outside someone’s window, and serenade them with your favorite nineties R&B tune, perhaps “All My Life” by K-Ci & JoJo?

For that we had to investigate.

CALLING VERSUS TEXTING

“A phone call? The WORST.”

—FEMALE FOCUS GROUP PARTICIPANT

“If you want to talk to me, you’re going to have to call me.”

—ANOTHER FEMALE FOCUS GROUP PARTICIPANT

[Dumbfounded]

—EVERY GUY IN THAT FOCUS GROUP

The issue of calling versus texting generated a wide variety of responses in our focus groups. Generally, younger dudes were fucking terrified of calling someone on a phone. This didn’t surprise me that much, but I was surprised that younger women also expressed terror at the thought of a traditional phone call. “Phone calls suck and they give me anxiety,” said one twenty-four-year-old woman. “Since texting started, an actual phone call feels like an emergency,” said another. Other girls thought it was just too forward for someone to call as the first move and said that a text would be more appropriate in general.

However, other women said receiving a phone call from a guy showed he had confidence and helped separate those men from the pack of generic “Hey wsup” texts that normally flood their messaging programs. To these women, the guys who call seem brave and mature. The phone conversations helped create a rapport that made them feel comfortable and safe enough to go out with a person they didn’t know all that well.

A woman who came to one of our focus groups discussed how she got so fed up with text messaging that she cut off her texting service and could only be reached by phone calls. This woman never went on a date with a man again. No, she actually started dating someone soon afterward. She also claimed the guys who did work up the courage to call her were a better caliber of man and that she was, in effect, able to weed out a lot of the bozos.

But with some women who loved phone calls, things weren’t that simple. In a rather inconvenient twist for would-be suitors, many said they loved phone calls—but had no interest in answering. “I often don’t answer, but I like receiving them,” said one woman, who seemed oblivious to how ridiculous this statement sounded.

For this group, voice mails provided a screening system of sorts. When they explained this, it made sense to me. If the message was from someone they’d met briefly at a bar, it let them hear the guy’s voice and made it easier to sort out the creeps. One girl raved about a nice voice mail a guy had recently left her. I kindly requested she play it and heard this gem: “Hey, Lydia. It’s Sam. Just calling to say what’s up. Gimme a ring when you get a chance.”

THAT WAS IT.

I pleaded to know what was so great about this. She sweetly recalled that “he remembered my name, he said hi, and he told me to call him back.”

Never mind the fact that what she described was the content of LITERALLY EVERY VOICE MAIL IN HISTORY. Name, hello, please call back. Not really a boatload of charm on display. To fail this test, a guy would have to leave a message that said: “No greeting. This is a man. I don’t remember you. End communication.”

When you look at overall numbers on communication, you see that we are generally texting more and calling less. According to Nielsen, Americans’ use of phones for voice calls peaked in 2007; we’ve been calling less, and speaking for fewer minutes, ever since.5

This change in communication may have some side effects, though. In her book Alone Together, MIT social psychologist Sherry Turkle convincingly makes the case that younger people are so used to text-based communications, where they have time to gather their thoughts and precisely plan what they are going to say, that they are losing their ability to have spontaneous conversation. She argues that the muscles in our brain that help us with spontaneous conversation are getting less exercise in the text-filled world, so our skills are declining.

When we did the large focus group where we split the room by generation—kids on the left, parents on the right—a strange thing happened. Before the show started, we noticed that the parents’ side of the room was full of chatter. People were talking to one another and asking how they had ended up at the event and getting to know people. On the kids’ side, everyone was buried in their phones and not talking to anyone around them.

It made me wonder whether our ability and desire to interact with strangers is another muscle that risks atrophy in the smartphone world. You don’t need to make small talk with strangers when you can read the Beverly Hills, 90210 Wikipedia page anytime you want. Honestly, what stranger can compete with a video that documents the budding friendship of two baby hippopotamuses? No one, that’s who.

At a minimum, young people are growing anxious about real-time phone conversations with people they don’t know well, and particularly with potential dates. “I have social anxiety, and having to respond or react on the spot to a phone call or in person would make me overanalyze everything and put myself in a tizzy,” one young woman told us. “I would want to take my time and think of a response that is genuine.”

The obvious advantage of a text is that a guy can text someone without having to gather the courage needed for a phone call. If you accept Turkle’s notion that men are also in general getting worse at spontaneous conversation, it makes sense that this trend will continue to climb.

I discussed this change in communication with Turkle in Los Angeles, and she brought up an interesting thought about getting asked out over the phone back in the day. “When a guy called and asked you out back then, it was a very special thing. You felt special and it was very flattering that he gathered the courage to do it.”

When I discussed what I had heard from the interviews with young people today, Turkle said that being asked out through a text message has become so banal that it no longer gives women that sense of flattery. As far as they know, the guy who has sent the message is hitting up lots of women and waiting to see who writes back. Unless he has sent something truly distinctive and personal, a text just isn’t all that meaningful.

After many conversations with women in the single world, I must concur.

THE MODERN BOZO

One firm takeaway from all our interviews with women is that most dudes out there are straight-up bozos. I’ve spent hours talking with women and seeing the kind of “first texts” they get from guys, and trust me, it’s infuriating. These were intelligent, attractive, amazing women and they all deserved better.

Some people say that it doesn’t matter what you text someone. If they like you, they like you. After interviewing hundreds of singles, I can scientifically confirm that this is total bullshit.

For those who doubt me, here is an example from a show I did at the Chicago Theatre in the spring of 2014.

During that tour, after doing material about texting, I would ask if anyone in the audience had recently met someone and had been texting back and forth. If they had, they would come up to the stage and I would pick a few people and read, analyze, and ask them about what was happening in their messages.

At this particular show I was speaking with Rachel, who had met a guy at a good friend’s wedding. As it happened, the guy was also a friend of her sister’s, so he had a pretty good shot at a first date with her. She was single. She was interested. All he had to do was send her a simple message introducing himself and asking her to do something.

Here’s what happened.

He sends his first message:

As soon as I said “texty,” it was clear that no one sitting in the 3,600-seat Chicago Theatre would ever fuck this dude in a million years. “Texty,” for whatever reason, seemed to be unequivocally disgusting to every one of us there.

He might as well have added: “BTW I have a really disgusting next-level STD! Haha :-) but for real I do.”

Rachel wrote back ten minutes later:

He wrote back shortly:

Rachel never met Will. After a few messages of this nature, Rachel stopped responding. None of us know Will. He may be a kind, handsome man with a heart of gold. But all we have to go on is those messages. And those messages have shaped in our minds a very dorky, terrifyingly Caucasian weirdo. Everything from “texty” to “tooooootally” to “Feliz Cumplea?os as well!” had destroyed all chances of Rachel’s wanting to meet Will in real life. So please, don’t let anyone tell you what you text someone doesn’t matter. If they don’t believe you, “texty” introduce them to Will and they’ll toooooootally change their mind.

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. In Alone Together Sherry Turkle tells the story of a young boy who had a standing appointment for a Sunday dinner with his grandparents. Every week, he’d want to cancel and his mom would tell him to call his grandparents and tell them he wasn’t coming. However, he never would, because he couldn’t bear to hear the disappointment in their voices. If it were text, though, he probably wouldn’t have thought twice about it. As a medium, it’s safe to say, texting facilitates flakiness and rudeness and many other personality traits that would not be expressed in a phone call or an in-person interaction.

Beyond flakiness, as far as dating goes, I’ve observed many men who, while hopefully decent human beings in person, become sexually aggressive “douche monsters” when hiding behind the texts on their phone. The messages being sent are inarguably inappropriate and often quite offensive, but, again, over text the consequences of the recipient’s being offended are minimal. You don’t see their face. You don’t hear their voice. And they aren’t there in person to look horrified or throw a heavy object at your dumb head.

On the other hand, on the tiny off chance they are interested, you are all set. It’s this dim hope that many dumb dudes are clinging to when they send these painfully obnoxious texts.

A website called Straight White Boys Texting has become a hub for women to submit these horrifying (and often hilarious) texts that guys have sent them.

As described on the site, the blog came about due to the phenomenon in which a guy texts an inept sexual advance like “hey what’s your bra size ;)” or “what would you do if you were here haha lol ;)” apropos of nothing, in order to try to hook up with someone.

This was known as a “straight white boy text,” hence the name of the blog, but, to be clear, the site is inclusive of douchey dudes of all races, ethnicities, and sexual orientations.

Here are a few favorites of mine:

This gentleman wastes no time. What’s interesting to me, though, is would this guy ever act this way in real life? Doubtful that he’d just go up to a woman and say, “Afternoon sex?” and wink at her—unless he was some kind of R&B superstar, in which case he’d be doing it all the time and it would possibly be quite successful.

Here’s another:

Again, I have to assume if this guy met this woman at a bar, his introduction would be something better than “I like your tits.”

The site, and women’s phones everywhere, are filled with cringeworthy exchanges like this. And clearly, these are extremely horrible messages. But from our interviews we learned that even for men who don’t write such blatantly disgusting nonsense, the smallest changes in what they text on a screen can make a huge difference in their dating success face-to-face.

Sometimes guys who have made a good impression in person and are on the verge of a true connection decide to send something dumb and awful and totally screw things up. Sure, there are extremes, like the woman who immediately lost interest after a guy asked her to Snapchat a photo of “just one boob.”

However, the mistakes people make are not always so egregious. We repeatedly found that one text can change the whole dynamic of a budding relationship. In a certain context, even just saying something as innocuous as “Hey, let’s hang out sometime” or spelling errors or punctuation choices can irritate someone. When I spoke with Sherry Turkle about this, she said that texting, unlike an in-person conversation, is not a forgiving medium for mistakes.

In a face-to-face conversation, people can read each other’s body language, facial expressions, and tones of voice. If you say something wrong, you have cues to sense it and you have a moment to recover or rephrase before it makes a lasting impact. Even on the phone you can hear a change in someone’s voice or a pause to let you know how they are interpreting what you’ve said. In text, your mistake just sits there marinating on the other person’s screen, leaving a lasting record of your ineptitude and bozoness.

• • •

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.

The phone self is defined by whatever it is you communicate onto the other person’s screen. I interviewed many women who told me that they didn’t always have sharp memories of guys to whom they gave their numbers after a conversation in a bar or over drinks at a party. In that context, the first message they get can be a huge factor in whether they reach back, and the phone self that’s presented makes all the difference. As you saw with the example with Rachel, even small tweaks of a text message can make the difference between being perceived as nice or mean, smart or dumb, funny or boring.

In our interviews and focus groups, people in all parts of the world generously opened up the secret world in their phones. I’ve probably scrolled through more text message conversations than anyone and asked men and women what we all are wondering: What was going on in your head when you read/wrote that? What did you think of this guy/girl when you read this message? It was so fascinating to see how people’s words could evoke such a wide range of reactions.

Let’s first look at the things that irritated people the most.

THE GENERIC “HEY” TEXT

After seeing hundreds and hundreds of messages in women’s phones, I can definitively say that most of the texts women receive are, sadly, utterly lacking in either thought or personality. Want to know what’s filling up the phones of nearly every single woman? It’s this: “Hey,” “Hey!” Heyyy!!” “Hey what’s going?” “Wsup,” “Wsup!” “What’s going on?” “Whatcha up to?”

It seems like a harmless message to send, and I’ve surely sent a good number of them in my own dating life. I and all the others who have sent similar messages surely meant no offense. However, seeing it from the other side is eye-opening. When your phone is filled with that stuff, generic messages come off as super dull and lazy. They make the recipient feel like she’s not very special or important to you.

Oh, and in case you’re a dude and you’ve never seen what your “Hey” texts look like when you send them, serially, here’s another post from Straight White Boys Texting:

THE SECRETARY PROBLEM

Another irritating situation that plagues both men and women is the endless texting banter that never leads to a meet in the real world. So many people trying to make a connection wind up spending so much time typing and typing and trying to schedule things that eventually whatever spark may have been there diminishes. At our focus groups we heard countless variations of an interaction that goes something like this:

Four days later.

Nine days later.

Six days later.

At this point the conversation ends. It’s amazing to see this exchange go from its fun and flirtatious opening to just plain fizzling out. And you can see how it happens: They go from enjoying the banter to trying to schedule something concrete, and all of a sudden they’re acting like secretaries.

The other annoying thing about this scheduling banter is that both parties are sometimes left wondering whether the person is actually busy or pretending to be busy, leading to more confusion and frustration. When you’re involved in this kind of back-and-forth, it’s hard not to wonder whether the other person even has interest.

THE ENDLESS BACK-AND-FORTH

Scheduling chatter is merely one of the many forms of useless banter that makes dating in the digital age so frustrating, especially for women over twenty-five, since they have less patience for constant text exchanges. Another form, which is especially common among the younger gentlemen out there, emerges when a dude is just too shy to actually ask the other person to do something. Instead of negotiating times and places, they wind up exchanging meaningless texts ad nauseam.

I can’t tell you how many girls I met who were clearly interested in a guy who, instead of asking them out, just kept sucking them into more mundane banter with gems like “So where do you do your laundry” What follows are ten back-and-forths about laundry detergent. (“Yeah, I recently switched to fragrance-free detergent. It’s been FANTASTIC.”)

At a stand-up show I did in Tulsa, I met a young man named Cody. He came onstage and we read through his text messages. There were literally twenty messages of useless, nervous banter. It was clear this woman was interested, but poor Cody simply wasn’t asking her to do anything. I told Cody he should just ask her out. He texted her, “Hey Ally. Have you been to Hawaiian Brian’s? Let me know if you want to go this week?” Within two hours she said yes, and they enjoyed a delicious meal at Hawaiian Brian’s the next week.

On a side note, is there any place on earth that sounds like it has a more chill vibe than Hawaiian Brian’s? Or for that matter, is there a chiller name than “Hawaiian Brian”? “Damnit! Hawaiian Brian just stole my debit card and liquidated all my bank accounts!” I can’t ever see someone having to utter that sentence.

GRAMMAR/SPELLING

In any interviews we did, whenever bad grammar or spelling popped up, it was an immediate and major turnoff. Women seemed to view it as a clear indicator that a dude was a bozo. Let’s say you are a handsome, charming stud who really made a great first impression. If your first text is “Hey we shud hang out sumtimez,” you may just destroy any goodwill you have built up.

On our subreddit we were told a story about a man who was dating a spectacular woman but eventually broke up with her. He said it went downhill once he texted her asking if she had heard about a party at a mutual friend’s house. Her response was “Hoo?” Not “Who,” but “Hoo.” He kept trying to force the word “who” into conversation to make sure this beautiful woman could spell a simple three-letter word. Every time, she spelled it “hoo.” He said it ruined everything. (NOTE: We did confirm that this was a woman and not an owl.)

ARE WE “HANGING OUT” OR GOING OUT ON A DATE?

Another thing that really pisses women off is when dudes ask them to “hang out.” The lack of clarity over whether the meet-up is even an actual date frustrates both sexes to no end, but since it’s usually the guys initiating, this is a clear area where men can step it up.

“It’s becoming too common for guys to ask girls to ‘hang out’ rather than directly asking them on a date,” said one woman. “I’m not sure if it’s because guys are afraid of rejection or because they want to seem casual about it, but it can leave one (or both) people unsure about whether or not they’re even on a date.”

When you are forward in this regard, it can really help you stand out from the crowd. A girl from our subreddit recalled meeting a guy at a loud party: “After I left he texted me, ‘Hi [name redacted], this is [first name, last name], we’re going on a date.’ His confidence, straightforwardness, and refreshingly gentlemanly approach (vs. skirting around ‘lets hang out some time’) made for an incredible first impression and had a lasting effect.”

THE GOOD TEXTS

Not all guys are bozos. We also found some really great texts that gave me hope for the modern man. While a phone call may be great, the advantage of texting is that it can allow a guy or girl to craft a great, thoughtful message that can build attraction.

We were also able to spot some specific traits these successful texts shared. After speaking with hundreds of men and women, the following three things seemed most important.

A FIRM INVITATION TO SOMETHING SPECIFIC AT A SPECIFIC TIME

There is a monumental difference in the fortunes of the guy who texts a girl, “Hey wuts goin on?” versus “Hey Katie, it was great meeting you on Saturday. If you’re around next week, I would love to take you to dinner at that restaurant we were talking about. Let me know if you’re free.”

These two guys could have the same intentions and feelings in their hearts, but the girl they’re texting will never know that. She’s going to decide whom to go out with based in part on how she interprets the short little messages that pop up on her phone. The lack of specificity in “Wanna do something sometime next week?” is a huge negative to women. The people interviewed overwhelmingly preferred to have a very specific (and ideally interesting and fun) thing presented with a firm invitation.

SOME CALLBACK TO THE LAST PREVIOUS IN-PERSON INTERACTION

This proves you were truly engaged when you last hung out and seemed to go a long way with women. One guy remembered that a girl was moving and in his text said, “I hope your move went well.” The woman we interviewed brought this up and said it had happened years ago but she still remembered it.

Another gentleman shared a story on the subreddit where he met a girl at a bar and they talked for a while and at some point he brought up the band Broken Bells and recommended she check it out. The next morning he received a text saying, “I think October is my favorite song on the Broken Bells album.” “October” was also his favorite song on the album. “Not only did she listen to my recommendation, but we connected in a very strong way. That was the beginning of the conversation, and we’ve been talking since,” he said.

There was also this story from a young woman: “One time, I met a guy at a party. When I got home, he texted me, ‘good night little Audrey.’ That’s not my name. I figured he was just too drunk to remember. After I confronted him about this, he said that he called me Audrey because I told him that I looked up to Audrey Hepburn. It was actually pretty sweet.”

I hope you aren’t holding an ice cream cone against your chest, ’cause your heart just warmed—and your ice cream just melted.

A HUMOROUS TONE

This is dangerous territory because some dudes go too far or make a crude joke that doesn’t sit well, but ideally you both share the same sense of humor and you can put some thought into it and pull it off. And when it’s pulled off well, the attraction to a similar sense of humor can be quite strong.

Here’s a story from the subreddit: “I met her at a bar in town, 2–3 AM after getting her number I drunkenly text her, ‘I’m that tall guy you made out with.’ In the morning I woke up to a message that said, ‘which tall guy?’ I was incredibly impressed with her sense of humor and we’re still together 2.5 years later.”

THIS IS JUST THE BEGINNING . . .

So this is what I’ve learned about initial asks, but that’s just the beginning. Even if you put out a solid ask, you are subject to a mountain of confusion. The person could be busy—or are they just pretending to be busy? They could give you silence, like I got! The adventure is just starting. Since everyone now has an entire social world in their phone, they’re carrying around a device that’s loaded with all kinds of back-and-forth, drama, and romance. Navigating that world is interesting, and what happens when you explore someone else’s phone world is nuts.

AFTER THE ASK . . .

So you’ve fired off a successful text, or maybe you’ve just received one. If you are one of the growing number of people evaluating and making plans with potential romantic partners via text messages, the games are just beginning. Unlike phone calls, which bind two people in real-time conversations that require at least some shared interpretation of the situation, communication by text has no predetermined temporal sequencing and lots of room for ambiguity. Did I just use the phrase “predetermined temporal sequencing”? Fuck yeah, I did.

In one of our first focus groups, a young woman, Margaret, told us about a gentleman she’d met at work. He sounded charming and she was definitely interested in him. I asked to see her text exchanges and immediately noticed that his name, according to her iPhone, was “Greg DON’T TXT TIL THURSDAY.”

So it was clear why these texts were important. These early communications could be the determining factor in whether she would one day become Margaret DON’T TXT TIL THURSDAY and make a family of little DON’T TXT TIL THURSDAYs of their own.

Margaret later explained that the last name she gave this guy was not his name but, in fact, an extreme step she was taking to avoid sending this dude a message for a few days, so as not to seem too eager and to ultimately make herself more desirable. The fear of coming off as desperate or overeager through texting was a common concern in our focus groups, and almost everyone seemed to have some strategy to avoid this deadly pitfall. There is no official guidebook anywhere on texting yet, but a cultural consensus has slowly formed in regard to texts. Some basic rules:

• Don’t text back right away. You come off like a loser who has nothing going on.

• If you write to someone, don’t text them again until you hear from them.

• The amount of text you write should be of a similar length to what the other person has written to you.

• Carrying this through, if your messages are in blue and the other person’s messages are green, if there is a shit ton more blue than green in your conversation, this person doesn’t give a shit about you.

• The person who receives the last message in a convo WINS!6

THE SCIENCE OF WAITING

The one area where there was much more debate was the amount of time one should wait to text back. Depending on the parties involved, it can become a very complicated and admittedly somewhat silly game with many different viewpoints on how to play—and win. As one woman told us, “There is this desire, for me at least, to have the upper hand. I have to have it. So if I text someone, and they wait ten minutes to text me back, I wait twenty. Which sounds stupid, but the way I see it, he and I both know the other is glued to their phone. Everyone is. So if you’re gonna play the game, that’s fine, but I’ll play it better. Very competitive.”

DAMN.

Several people subscribed to the notion of doubling the response time. (They write back in five minutes, you wait ten, etc.) This way you achieve the upper hand and constantly seem busier and less available than your counterpart. Others thought waiting just a few minutes was enough to prove you had something important in your life besides your phone. Some thought you should double but occasionally throw in a quick response to not seem so regimented (nothing too long, though!). Some people swore by waiting 1.25 times longer. Others argued they found three minutes to be just right. There were also those who were so fed up with the games that they thought receiving timely responses free of games was refreshing and showed confidence.

But does this stuff work? Why do so many people do it? Are any of these strategies really lining up with actual psychological findings?

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.

I personally find the idea that this stuff works very frustrating. If someone is really into me and showing interest, shouldn’t I just appreciate that and welcome those advances? Why do we want what we can’t have and sometimes have more attraction to people when they seem a little distant or disinterested?

THE POWER OF WAITING

In recent years behavioral scientists have shed some light on why these waiting techniques can be powerful. Let’s first look at the notion that texting back right away makes you less appealing. Psychologists have conducted hundreds of studies in which they reward lab animals in different ways under different 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.7

If a text back from someone is considered a “reward,” consider the fact that lab animals who get rewarded for pushing a lever every time will eventually slow down because they know that the next time they want a reward, it will be waiting for them. So basically, if you are the guy or girl who texts back immediately, you are taken for granted and ultimately lower your value as a reward. As a result, the person doesn’t feel as much of an urge to text you or, in the case of the lab animal, push the lever.

• • •

Texting is a medium that conditions our minds in a distinctive way, and we expect our exchanges to work differently with messages than they did with phone calls. Before everyone had a cell phone, people could usually wait awhile—up to a few days, even—to call back before reaching the point where the other person would get concerned. Texting has habituated us to receiving a much quicker response. From our interviews, this time frame varies from person to person, but it can be anywhere from ten minutes to an hour to even immediately, depending on the previous communication. When we don’t get the quick response, our mind freaks out.

MIT anthropologist Natasha Schüll studies gambling addiction and specifically what happens to the minds and bodies of people who get hooked on the immediate gratification that slot machines provide. When we met in Boston, she explained that unlike cards, horse races, or the weekly lottery—all games that make gamblers wait (for their turn, for the horses to finish, or for the weekly drawing)—machine gambling is lightning fast, so that players get immediate information.

“You come to expect an instant outcome, and you stop tolerating any delay.” Schüll drew an analogy between slot machines and texting, since both generate the expectation of a quick reply. “When you’re texting with someone you’re attracted to, someone you don’t really know yet, it’s like playing a slot machine: There’s a lot of uncertainty, anticipation, and anxiety. Your whole system is primed to receive a message back. You want it—you need it—right away, and if it doesn’t come, your whole system is like, ‘Aaaaah!’ You don’t know what to do with the lack of response, the unresolved outcome.”

Schüll said that texting someone is very different from leaving a message on a home answering machine, which we used to do in the days before smartphones. “Timewise, and also emotionally, leaving a message on someone’s machine was more like buying a lottery ticket,” she explained. “You knew there would be a longer waiting period until you found out the winning numbers. You weren’t expecting an instant callback and you could even enjoy that suspense, because you knew it would take a few days. But with texting, if you don’t hear back in even fifteen minutes, you can freak out.”

Schüll told us that she has experienced this waiting distress firsthand. Several years ago she was texting with a suitor, someone she’d starting dating and was really into, and he gave every indication that he was really into her too. Then, out of nowhere, the guy went silent. She didn’t hear back from him for three days. She got fixated on the guy’s disappearance and had trouble focusing or even participating in ordinary social life. “No one wanted to hang out with me,” she said, “because I was just obsessed, like, What the fuck? Where the fuck is this guy?”

Eventually the guy reached out and she was relieved to find out that he’d actually legitimately lost his phone, and since that’s where he’d stored her number, he had no other way of getting in touch with her.

“With a phone call, three days of silence probably wouldn’t drive you that crazy, but with my mind habituated to texting, the loss of that reward . . . Well, it was three days of pure hell,” she said.

Even people in relationships experience this anxiety with texting. In my own relationship, which is a committed, loving partnership, I’ve experienced several instances of a delay in text causing uneasiness. Here’s an example:

Note the twenty-minute gap here.

In the gap after “Want to meet us?” I was sure she was mad about something. Her responses had been pretty immediate, and it seemed like her pause was an indicator that something was wrong and that I should have been going to the hotel or something.

Note the time gap here as well.

Again, when she didn’t respond after “Is that a grump txt or not” I was certain she was grumpy, because why wait so long to tell me she’s not grumps? All of this change in my perception of her feelings and my own mood was purely because of the temporal differences in texting.

Even in nonromantic situations, waiting has caused uneasiness. I texted an acquaintance about reading a draft of this very book. I wrote: “Hey would you have any interest in reading an early draft of my modern romance book? Just want to get some eyes on it and I feel like you’d get the tone I’m going for and have good feedback. If you’re too busy etc, no offense taken.”

The text was sent at 1:33 P.M. on a Wednesday and got an immediate “Read 1:33 P.M.” But I didn’t hear back until 6:14 P.M. the next day. During the time that passed, I worried that maybe I’d overstepped my bounds in our friendship, that it wasn’t proper for me to ask, etc. In the end I’d worried for nothing and he wrote back, “yeah, of course! sounds like fun . . .”

If the effect is this powerful for people in committed relationships and friendships, it makes sense that all the psychological principles seem to point to waiting being a strategy that works for singles who are trying to build attraction.

For instance, let’s say you are a man and you meet three women at a bar. The next day you text them. Two respond fairly quickly, and one of them does not respond at all. The first two women have, in a sense, indicated interest by writing back and have, in effect, put your mind at ease. The other woman, since she hasn’t responded, has created uncertainty, and your mind is now looking for an explanation for why. You keep wondering, Why the fuck didn’t she write back? What’s wrong? Did I screw something up? This third woman has created uncertainty, which social psychologists have found can lead to strong romantic attraction.

The team of Erin Whitchurch, Timothy Wilson, and Daniel Gilbert conducted a study where women were shown Facebook profiles of men who they were told had viewed their profiles. One group was shown profiles of men who they were told had rated their profiles the best. A second group was told they were seeing profiles of men who had said their profiles were average. And a third group was shown profiles of men and told it was “uncertain” how much the men liked them. As expected, the women preferred the guys who they were told liked them best over the ones who rated them average. (The reciprocity principle: We like people who like us.) However, the women were most attracted to the “uncertain” group. They also later reported thinking about the “uncertain” men the most. When you think about people more, this increases their presence in your mind, which ultimately can lead to feelings of attraction.8

Another idea from social psychology that goes into our texting games is the scarcity principle. Basically, we see something as more desirable when it is less available. When you are texting someone less frequently, you are, in effect, creating a scarcity of you and making yourself more attractive.

WHAT WE DO WHEN WE ARE INTERESTED

Sometimes there’s another reason that people take so long to text you back: They aren’t playing mind games or busy. They’re just GOOGLING THE FUCK OUT OF YOU.

In one 2011 survey, more than 80 percent of millennials admitted to doing online research on their partner before a first date.9 And why not? With our expanded dating pools, we’re meeting people we hardly know, including total strangers with no existing social ties to us. Fortunately, the same technology that allows us to connect with them also helps us figure out whether they post cute pictures of baby elephants or something more malicious, like a blog chronicling their latest elephant-poaching expedition in Botswana.

Usually Internet research turns up little more than some basic biographical information and a smattering of photographs from Facebook and Instagram. Some singles said even this relatively minimal content is helpful, because it gives them clues about people’s interests and character before meeting them. That makes sense to me, since you could argue that the photos posted on an Instagram page offer a more compelling and realistic representation of someone than their carefully crafted online dating profile.

Others see the process as harmful, though, because reading too much of a person’s online history can deprive them, and their date, of the fun of discovering someone new. Some singles we spoke with described meeting a person and being unable to enjoy the date because they already had all kinds of preconceived notions that were difficult to block out.

One gentleman I met told me that the personal information we can so easily obtain online often causes him to be too harsh on people. “I’ll go through and look at their entire timeline of tweets. I’ll see one dumb thing I don’t agree with, and then I kind of mentally check out on the date,” he said.

It may be harsh to judge someone’s personality off a tweet or two, but if you’re serious about your research, the Internet offers a whole lot more information than that. When we posed the question of first-date Internet research to the subreddit, we heard some serious horror stories.

One woman recounted canceling a date after a brief bit of research:

I googled my date who had a very distinctive name. According to a weekly synagogue newsletter, he and his wife were hosting a Torah class for children in their home the same day as our date.

This has also been recorded as the only time in history someone has said, “Whew, I’m glad I read that weekly synagogue newsletter.”

Other stories were even more horrific.

One woman wrote:

[A] friend from work met a firefighter in a bar a few months ago. They talked a lot that night/exchanged numbers and were texting back and forth for the next week while setting up a first date. He told her he didn’t have a facebook and when she mentioned that to some other people, they told her she should be concerned that he might be lying and actually have a girlfriend or be married. So she google searched his name + LA fire department and found that there was a news story on him (with a video!) about how he AND HIS MOTHER beat up an elderly woman who was feeding stray cats on their street. She immediately stopped talking to him.

This is why I always say: If your mother asks you to come beat up an elderly woman on the street for feeding stray cats—JUST SAY NO. It’ll always come back to haunt you.

WHAT WE DO WHEN WE AREN’T INTERESTED

If you are just plain not interested in someone, you have a whole other conundrum to deal with. How should you let this person know you aren’t interested? From our interviews, it seems there are three big approaches: pretend to be busy, say nothing, or be honest.

In every stop on my tour, from San Francisco to London to Wichita, I asked audiences which method they used. In total, this was more than 150,000 people, and in every audience, a sample size of a few thousand, the response was always the same. Overwhelmingly, most people practice the “pretend to be busy” and “silence” methods. Only a small sliver of the crowd would say they were honest.

However, when I flipped the situation and said, “Okay, now pretend the situation is reversed. Someone else is dealing with you. How do you prefer they handle the situation? Clap if you prefer they pretend to be busy.”

A smattering of claps.

“Clap if you prefer they say nothing, that they give you silence.”

A smaller smattering.

“And finally, clap if you prefer that they are honest with you.”

Basically, the whole audience would applaud.

Why do we all say we prefer honesty but rarely give that courtesy to others? Maybe in our hearts we all want to give others honesty, but in practice it’s just too damn hard. Honesty is confrontational. Crafting the “honest” message takes a lot of time and thought. And no matter how delicately you do it, it feels cold and mean to reject someone. It’s just easier on many levels to say nothing or pretend to be busy until people get the picture.

Do we really prefer to get the cold, hard truth when someone is rejecting us, though? We don’t respond well to rejection, especially when we’ve put ourselves out there and shown interest in another person, and it’s painful to read a message saying that someone doesn’t want to date you.

If we’re 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.

This way, our feelings aren’t hurt and we aren’t left confused or frustrated by silence or “pretend to be busy” issues. So I guess what I’m saying is the next time someone asks you out and you aren’t interested, the nicest thing you can do is write back: “Sorry, can’t do dinner tomorrow. I’m leaving on a secret mission with the space program! When I return to earth, I will have barely aged at all, but you’ll be seventy-eight years old. I just don’t think it’s a good time for me.”

WHAT HAPPENED WITH TANYA, THOUGH?

The thing to remember with this nonsense is, despite all your second-guessing about the content or timing of your message, sometimes it’s just not your fault and other factors are at play. When I was dealing with the Tanya situation, one friend gave me the best advice, in hindsight. He said, “A lot of times you’re in these situations and you second-guess the things you said, did, or wrote, but sometimes it just has to do with something on their end that you have no clue about.”

A few months later I ran into Tanya. We had a lot of fun together and she eventually told me that she was sorry she didn’t get back to me that time. Apparently at the time she was questioning her entire sexual identity and was trying to figure out if she was a lesbian.

Well, that was definitely not a theory that crossed my mind.

We ended up hooking up that night, and this time she said there would be no games.

I texted her a few days later to follow up on this plan.

Her response: silence.*