For Italians, nothing shows affection like a home-cooked meal. For Cancerians like me, who are also Italian, the preparation of food is nothing short of a love letter. Last night, when mia cara amica (my dear friend), Marcy, entered my home, I realized how much our friendship has deepened over the past few years; the highlight of my day was cooking Bolognese sauce for her, one of my two favorite winter dishes.

Our friendship is unique, to be sure. We both married our college sweethearts—and later divorced them. When we met, I was already past the split with my husband, but she was just beginning hers. Since then, we’ve come to discover life with new eyes as emancipated 30-somethings—which is different from our single friends, and worlds apart from most of our peers, nearly all of whom are married with children.

Our lives may not always reach the glamour of Sex and the City, but they are certainly filled with a similar abundance of choice and freedom, something that many women our age won’t ever experience. With financial independence—and without families to support—Marcy and I can do whatever we want whenever we want. We can enjoy the privacy of our homes or stay out all night; we can place our undivided focus towards our friendships, careers, or relationships. We can lock our front doors behind us and live in Italy for two months without asking permission.

These are not the rules that we were raised to follow; instead, we’re making them up as we go along. It’s disconcerting and reassuring at the same time. We are the goddesses of all creation.

Naturalamente, there are times when we feel like we’re on the outside—being single isn’t always a party—but it does comes with special benefits, like the ability to live in a state of unending possibility. New attractions can come into our lives at any time and we’re free to explore them, and no experience so elementally expresses that propitious condition of opportunity as a first date.

On Thursday, as I walked underneath a shower of snowflakes to meet John at The Sitting Room, I pondered how technology plays a key role today in drawing people together, including the two of us. Some subscribe to online dating or message boards, whereas last weekend my iPad became the lingua franca as John and I as we sat next to each other at Caffe Fiore, listening to Charlotte sing from underneath the table behind us.

I had just purchased my iPhone and was still reveling in all ways it worked with my iPad, especially in being able to pair photos with my essays. (And I can kill zombies, but that’s a topic for another day.) An older gentlemen commented in passing on my iPad, then John chimed in from my right. 

We talked on and off for the duration of our stay. Embracing the spirit of possibility, I gave him my card before we parted ways. Three days later, he sent a perfectly timed email asking if I’d like to meet for a drink. (As I told the story, Marcy laughed in agreement: if we don’t hear from them after three days, they’re relegated to the Island of Lost Men.)

Days before we met up, John wrote to confirm logistics, admitting that he had trashed some of the older messages between us. I tested the waters by lobbing a little sass his way: “Deleting my emails already? Way to play it cool.” To my delight, he responded, “No kidding, at least I read it before my fingers became too quick for my own good!”

Sense of humor and quick wit—check. Humor is challenging to display through electronic communication; a soft yet clever touch is key—and so is the sophistication to pick up on it. Anyone who has ever composed an online profile or corresponded with strangers through a dating site knows this. Technology may unite us with people who we might not otherwise have met, but quickly delivered miscommunication can kill a budding relationship.

It was then that I realized how extensive our mental checklists can be when we date. In a lifetime’s collection of results, we become the summation of everyone we’ve dated, creating subconscious metrics to qualify and extract viable candidates for dating.

Why do we match with one person over another? It all comes down to points earned. Some people naturally score higher than others; and while chemistry is an important factor, even more important is compatibility. Sites like, EHarmony, and JDate have figured this out—hence the barrage of questions that an applicant must answer in order to prescreen a list of likely candidates into a shortlist of likelier ones.

In life, we assign or remove points with each conversation, each meeting, each thoughtful—or thoughtless—act. Points given for showing up on time, for sitting next to me rather than across from me at dinner, and for insisting on walking me home. Points removed for dressing like a slacker, waiting four days to respond to a message, or for laughing and continuing to eat without offering to flag down a waiter to replace the fork I just dropped.

In all of this is the cycle of alpha and omega. People meet online, in bars, on busses, and in coffee shops. Everything is new, except that by this point in life, we’ve experienced numerous beginnings and an equal number of endings.

At the start, there is pressure to remain noncommittal. We all feel it, even if we’re in search of a relationship: we find ourselves asserting our independence and busy schedules. We’re looking for signs of weirdness or weakness—anything that might suggest that we’re wasting our time.

Yet, in spite of our declared sovereignty, there are magic moments when it all becomes white noise—we linger at restaurants longer than we had intended, we begin to find time where before we insisted on our pre-set schedules. At that moment, we move past the realm of rules and ratings.

As a woman who is all about the in-person experience, I’m continually surprised at how technology can actually help the awkward process of dating. I can’t imagine the days when men had only the phone or a formal request at their disposal to arrange a first date, though perhaps the possibility of a blazing rebuke made the hunt more intriguing.

To me, the  best part about today’s system is that we can quickly evaluate a person’s ability to express himself through writing, which I consider a sneak peek into their complexity. I was pleased to discover that John composes lovely emails—thoughtful, to the point, well-written, light-hearted, and often amusing. A prominent category in my checklist, a man’s mastery of language is essential; while bordering on a bit removed, where would I be without email as an early screening process?

On our first date, three hours sped by like they were nothing, and I had to remind myself that it was Thursday night, not Friday. After John walked me home, I began to count the beads on my mental abacus. I paused to appreciate the significance of that moment, one that’s become familiar over the past five years: it’s the time before anything becomes a deal-breaker, the time of big ideas and great possibility. It’s like touching perfection, if only for an instant.

Picture it yourself, if it’s been awhile. Hours of conversation and red wine flow as you just begin to scratch the surface of knowing a new human being. Just like Carrie Bradshaw, you get to declare, “This is me,” as you approach your brick apartment building, relishing in the fact that you don’t know what happens next. After you say goodbye, you push the heavy front door open and are greeted by a rush of warm radiated air, tinged with the outflux of old wood. You ascend the winding stairs to your floor, eschewing the elevator in order to capture a few extra moments during which you replay parts of your conversation.

It was in this spirit that I entered my floor and stopped cold in my tracks.

A woman sobbed from the apartment next to the stairs, dissolving my smile and arresting my heart. A tenuous low twang drew out her cry. I could tell that she was on the floor. “I can’t…. I can’t feel this anymore,” she wept in punctuated syllables. “I can’t love him anymore; it hurts too fucking much.”

I was transfixed. I could picture her red face, eyes swollen with tears. Part of me wanted to knock on her door and offer her a hug, though we don’t know each other. She sobbed wordlessly for another minute on the other side of the door, losing her voice, which became a series of raspy heaves. Then suddenly, she cried out, “Why?! Why?! Whyyyyyyy?!”

I leaned against the corner of the hall, listening to her sobs trail down to animal sounds again. She sobbed so hard that my ribs felt sore. How poignant that, as I returned from connecting with someone new, I was met with a reminder of how love sometimes ends.

The next morning, upon reading an email from John—sent not too quickly to be desperate, but not too late as to be disinterested—I reaffirmed that it’s still worth taking a chance.

Like anything digital these days—even a well-composed essay—relationships are often camouflaged in simplicity at the start. We find ourselves surprised by the complex versions we end up with, based very loosely on what we thought we were originally sold.

Yet, whether it’s through pleasure or heartbreak, sometimes both, they always teach us about life and ourselves—and occasionally, a bit about technology.