It began with the hedge fund guy who crossed state lines for sex. When I read his sex diary, my expectations were low; they sunk to a nadir when I opened the e-mail introducing his submission:

I am a loyal reader, and this diary combines a decent week sexually with an insight into a complex psyche, if I say so myself.

A self-centered finance guy. Joy. Men like him were the downside of my side job: assigning and editing sex diaries—accounts of everything that happened in a week in an anonymous New Yorker's private life—for the Sex Diaries hub on New York magazine's website. Compared to my other jobs, writing for publications like The New York Times and Popular Science, this was the candy.

His was the 150th diary I'd read; the other 110 or so were by women in my demographic: late twenties, child-free, with the time and inclination to respond to my ads seeking diarists, usually spending a week hanging off various Manhattan and Brooklyn chandeliers, often fueled by a combination of alcohol, cocaine, and breakup. Their diaries made for great vicarious reading of lives I didn't want. I was serious about making it in New York, and that didn't include chandeliers and coke.

The finance guys were also all the same: pre-dawn CNBC market check, job, home, porn, sexting with women, not enough sleep—all of which they found fascinating. I set my egg timer, preparing to rush through his diary:

Overnight bag packed. I dash to the West 4th Street station to catch the train to JFK. I am on one of my swinging adventures to participate in an MFM threesome.

Well. Here was a twist—with a bang. He called in sick and flew to a flyover state, where he drove to a TGI Friday's, met a man and woman for drinks, followed by hotel sex, all filmed for posterity. The next day he caught a 6 a.m. flight back home.

My modus operandi is simple. Exchange recent pics of him and her [on Adult Friend Finder]. Talk on the phone. Set a date. Fly. Fuck like mad. Return to NYC. When it works, it is a very efficient way to get hot, no-strings-attached sex.

When my egg timer dinged, I kept reading. He was a jackass...

I told my shrink that I think I am a misogynist. She tells me I should listen to women more.... And I tell myself that I make too much money, look too good, and work too damn hard for this shit.

Yet his approach–direct and practical, getting what he wanted out of the world–stopped me. Creating precise sexual encounters had never occurred to me as an option. I dated to find a partner, and the sex was sort of haphazard, what happened when the friends-of-friends connections, social schedules, and my period all cooperated. I'd never thought of overtly planning for sex. But of course it makes sense to arrange it directly, rather than hoping three dinner dates would lead where I wanted. He appealed, I think, to my desire for hyperorganization and self-determination. I read his diary and thought, I could do this.

What this was, I still had no idea. I had no desire to arrange sex dates with unknown couples in flyover states. I published his diary and went on a spree of commissioning others that were far from my own experience: BDSM, kink, and a lot of gay men. His was my first inkling that I might learn from diaries of people very different from me.

When it comes to our private lives, we're all on our own paths. And it's really helpful to peek at other paths. The person and the path can be wildly divergent; the person can be offensively different from you, but his or her path similar. When you see a path you want to be on, you perk up. It stirs you.

My own path had recently slid into a ditch, leaving me sweeping up after yet another failed relationship. He was nice; I was nice. Our breakup conversation: him telling me it was over; me being cordial about it. Therein lay the problem. I was nice to the world. I had never actually asked the world for what I wanted. Thus I received a big, cordial pile of eh back.

Around this time a diary appeared in my inbox from a 42-year-old Chicago father, an executive at a well-known company. He was affable, mainstream, and in a deeply fulfilling, open 10-year-relationship with his gay partner. On the third day of his diary, he took his daughter to Wiggleworms class and then hopped a plane for a business trip. That night he wrote from Manhattan:

10:30 P.M.: Having a couple drinks with a friend I get together with when in New York. We actually met online abroad, when we were both there for work, and screwed around. More than that though, it is cool to have someone to hang out with. We often see each other without having sex, but sometimes we do [have sex]. When I'm away from home for a few days, it's a way of making emotional connections.

By then I'd read numerous diaries, countless magazines, piles of Russian literature, and much of my university's stacks on sex and relationships. Yet those sentences made more sense than anything I'd ever read. Of course it would be nice to have a dear friend with whom to occasionally have sexy times, and occasionally have friend times. Of course it would be particularly nice when traveling. Duh. Reading diaries had softened me up to the options, but I still didn't know you could just do that, and that your committed, long-term partner might agree to it, making the arrangement different from the standard fuckbuddy or fling. Here was a man who'd successfully created the existence he wanted for himself: employment, fun, children, committed partnership, long-term friends/lovers. There were no secrets, and no rules.

I stared at my box of a studio apartment. I'd been certain that I was a no-rules woman: living on my own, dating whomever I pleased, and generally flaunting my lifestyle of flying around the world on assignments and refusing to get a full-time job. Yet my definition of dating—find a person whom I might marry and spend the rest of my life with—was limiting. Anyway, it wasn't working: I wanted a serious boyfriend and didn't have one.

It was not lost on me that most of the diaries I was staring at in that period were written by men. Male diarists are typically much more expansive in their sense of options, and therefore so are their realities. What men excel at, I realized, is identifying what they want in the immediate term. Dudes know how they want to spend the next two weeks, or at least the night. They ask for it, and they're happier for it. I wanted that sense of determination, that ability to ask for what I wanted. I wanted out of the box.

In this line of work you end up surrounded by people who are extremely interested in sex and relationships, and one particular man had been asking me out—or asking me in—since 2005. Matt didn't want to date me; he just wanted to sleep with me. He had other lovers and a fairly serious girlfriend. In 2005, I thought he was sketchy. By 2008, I thought he had a brilliant idea. I e-mailed to arrange a date. He hit "reply" and asked me to e-mail him precisely what I'd like those two hours to consist of.

I'd seen this sort of planning before, among the kinkier diarists who weren't terribly aroused by vanilla sex. Most required specific stimulation to get off, whether that came from purposeful psychological stress, via role-playing and planned scenes, or physical stress, via paraphernalia (ropes, whips, etc.). A Seattle lawyer explained it well:

As you have probably gathered, I am drawn to more intense kinds of sexual experiences than others. I like things like BDSM and sensation play. I enjoy sexual contact that is much more intentional, and where connection is much more powerful.

As a result, he not only planned ahead, but was forced to state specifically what he'd like to happen. Very useful skills.

I e-mailed Matt my list of what I wanted to do, down to 10-minute increments. Imagine your list of Bedroom Things I Like Very Much. That was it. I also explained my safe sex requirements. He said sure.

When he arrived at my apartment after work on the arranged day, I felt calm. I had immersed myself in enough diaries to know approximately how this would go, and we were friendly, so that genuine connection—eye contact, joking—was easy. We ran through the plan verbally and then enacted it. For the first time, I had the unexpected experience of being able to simply receive and not worry about what was happening next, or how my partner was doing, or whether I was being selfish. You have no idea that you've never just been until it happens to you.

When it was over, we were famished. We went to the diner on the corner, and over chocolate cake served by a waiter I waved to daily, I felt more in control of my private life than I'd felt in the past decade. I'd done something intentional, and it had worked.

I soon learned why so many (predominantly male) diarists swear by such playdates. There is so much that is completely great about them. You spend the days in advance twitching with excitement because you know exactly what is going to happen, and that you're going to be totally into it. It's like a massage appointment, but better, since you can be even more bossy. Or you can be passive. Whatever you want. And then you glow for a day.

Arranging playdates required skills I'd never used before: identifying people I was sexually attracted to yet not at risk of emotional involvement with. Telling them this. Squashing the part of my brain used to equating sex with love. And crucially, setting boundaries, because when men learn that you're hypothetically available, you'd better have your wants and boundaries on the tip of your tongue.

On the outside, my life did not visibly change. I still dated people I thought might make good long-term partners, and over a year I racked up three playmates. I always came away grinning. Nothing bad ever happened. This was astonishing. I couldn't fathom why no one had ever told me this, and had I not edited diaries for a living, I never would have caught on. The most delicious, confidence-boosting part of my life came from whispering into a man's ear: "Would you like to have a playdate with me some time?" Only one person ever said no.

I met my boyfriend in this period, in another city at a friend's thirtieth birthday party themed "Birth of a Cougar." It was obvious from the moment we touched fingers that he was more soulmate than playmate. We dated nonexclusively, because that made sense for people who were 3,000 miles apart. By then I was spending my days reading diaries from people of all ages and four countries as I put together collections for Italian and British book editions, analyzing the myriad ways that people connect—or don't. On our visits, the most common phrase hollered across the apartment was, "Wanna try a good idea from a diary?" He always said yes. "This one's a 78-year-old grandmother from Bainbridge Island, Washington!"

Tuesday, 8:13 P.M.: Touching time. We just lie in bed together and please each other with a lot of petting and necking and kissing. We do it maybe once or twice a month. It's kind of like a date.

Or "Buddha sex," from a 40-year-old diarist:

There is a Chinese medicine tradition called `morning prayer' that my boyfriend likes to do: He enters me, holds me, looks into my eyes, only moving just enough to stay hard.

There is no more lovely way to wake.

My boyfriend moved in soon after. Given that we'd successfully had other partners through our first year of dating, I couldn't see a compelling reason to give up my playmates, and neither could he. (It helped that he was recently out of a 12-year monogamous marriage and valued freedom.) It was messy sometimes—new, open relationships always are, because you only learn what your boundaries are from your partner's stabbingly painful trial and error—but things stabilized. It worked. Because one's relationship life is as unique as one's bedside drawer. Whether you're perfectly happy with a rotating cast of lovers or a vibrator, who cares what it looks like, or what you call it? Once you've reasonably cared for the needs of those involved, you are the only one you have to answer to.

Rather than trying to define our relationship, I simply focused on it, with lots of together time. In the intervening years (it's been three now) a gentle definition arose, by watching what it is that we tend to do naturally. And what we do is this: enjoy and nurture our relationship and fill our lives with a select group of deeply trusted friends/lovers to dabble with when one of us is traveling or needs attention. It's a nuanced relationship that shifts to meet needs that themselves shift over time.

The day this article was due, my partner asked me to marry him. I gave an ebullient yes, and then that evening asked if he would ask again the next day, just so I could really savor it. As I knew from the diaries, planning ahead doesn't kill spontaneity; it creates a different kind of improvisation. So I spent that evening bouncing around because something reeeeally great was going to happen to meeeeee the next day. Today we were halfway engaged, but tomorrow we'd be fully engaged. It was among the happiest nights of my life. I knew that getting asked twice wasn't the norm, but it was what I wanted. So I asked for it.

Arianne Cohen is the author of the just published The Sex Diaries Project: What We're Saying About What We're Doing (Wiley).

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