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The Heart of Dating: The Debrief

Women Sitting on Sofa While Holding Cups

A few years ago, I found myself single in my late twenties, sharing an apartment with two colleagues-turned-friends-turned-flatmates who had also found themselves single around the same time. The three of us plunged into the world of heterosexual dating in the post-pandemic world much like a raft does into a Class V rapid, our only lifejackets being each other and the bits and pieces of wisdom we had accumulated through our dating misadventures. After two years spent in lockdown, my social skills were rusty, and making new friends as an adult in a new city felt very awkward. I couldn’t have contemplated dating again if it wasn’t for my flatmates, my intrepid companions. We helped each other select our best selfies for dating apps, stalked prospective dates online for red flags, and shared our location with each other to create some sense of safety when out meeting new people. But the most important role my girlfriends played in my dating life was after a date was over, when it was time for The Debrief.

The Debrief is a girlhood ritual as old as dating itself. As a millennial, I was part of arguably the first generation of urban Indians that not only gained a theoretical understanding of the concept of dating through popular media, but also accessed some opportunity to experiment with it as young adults before marriage. We grew up in a world of prepaid SIM cards, Café Coffee Day, MSN Messenger, Orkut profiles, Archies stores stocked with romantic gifts, and mall culture. These technologies and spaces enabled crushes, discreet flirting, secret relationships, and so on. As teenagers, our ideas about heterosexual romance and relationships were fashioned on templates provided by western books, movies, TV shows, and music that introduced popular tropes and gave us a vocabulary for dating. And whether it was books like The Princess Diaries and Sweet Valley High, or Lindsay Lohan and Hilary Duff high school movies, or sitcoms like Friends, or even songs by pop stars like Taylor Swift who sang as poignantly about her high school best friend’s first heartbreak as she did her own, the one thing they all established about dating was that it was NOT meant to be a solitary endeavour. In popular culture, every girl looking for love has an assortment of friends playing the roles of strategist, confidant, cheerleader, protector, stylist, therapist, wing woman, and sympathizer.

So when you add devoted girlfriends to dating drama, you get The Debrief: a group chat for women to describe, discuss, analyse, and process milestones in their love lives, most notably their interactions with men. Whether it’s a first date, a fight, a breakup, or an ex reaching out again, every development offers plenty to dissect.

Let me share an example of a memorable Debrief after an interesting first date I went on. I had been texting a guy I’d met online and we decided to have dinner one evening when he visited my city. We had connected over our similarities – we were both working at startups at the time, considered ourselves introverts, and were big fans of Shah Rukh Khan. We would text nearly every day and had progressed to bantering via memes. But I knew our first date would be the real test of chemistry, compatibility, and potential. The date went well – he was interesting, intelligent, and extremely polite. But there were hiccups too: he mentioned his ex more than once and seemed to be a little too casual about casually dating multiple women at the same time. At one point, he launched into a lengthy monologue about cricket, a sport I had no interest in. Unaffected by my attempts to subtly change the subject, he recapped the pivotal moments in the history of the sport for the better part of an hour. And though we both seemed to enjoy the date, it ended with ambiguity. I returned home unsure of how much I was interested in him and uncertain about whether he would want to keep talking to me and plan more dates.

Some clarity came during the first Debrief with my flatmates that began the second I walked through the door. To no one’s surprise, we ended up devoting more time recapping and footnoting the date than I had spent on the date itself. The Debrief is a muddled data dump meant to be raw, unfiltered, messy, confusing and very honest. It’s part of the processing stage that helps us formulate a coherent story of what happened by taking a step back from the experience and crafting a narrative that zooms in on the bits of dialogue and scenery that feel important, so we can arrive at an authentic account of our experience. The magic of the Debrief is that it is made to an audience that knows us well, cares deeply about our happiness, and engages enthusiastically by asking questions to challenge or affirm our interpretations of what we experienced. By listening attentively, probing deeper, making meaning of our haphazard narrative, and validating our feelings, our friends help us better understand the developments in our love lives and prepare for better or challenging days to come.

Although a Debrief is usually focused on one person’s one exciting romance-related experience, it often encompasses more than that. Dating means creating our own rules as we go along. Debriefs with our friends can expose us to alternate perspectives from trusted confidants that can gently lead us to re-examine our own comfort zones, deal breakers, and pros and cons lists. Everyone has their own definitions of what they think is desirable, icky, acceptable, and so on, so Debriefs often devolve into lively debates. Who should pay on a first date? Is it okay to make an excuse and leave early if there’s no spark? Is one date enough to gauge future potential? What are the best ways to politely but firmly reject a guy’s physical advances if one isn’t interested? Does dressing up too much seem desperate? How much is too much, anyway? And should men’s preferences even matter when we dress for dates? Most of my friends, for example, found the repeated, random mentions of my date’s ex-girlfriend concerning, seeing them as an indication that he wasn’t yet over her. I personally had been more annoyed by his long monologues on cricket that ignored my disinterest and forced me to smile and nod along politely, but my friends reminded me of his otherwise attentive and considerate behaviour. Later, during The Debrief of the same date given to my school friends in my hometown, one defended the lecture as possible nervous rambling, which made me feel a little more sympathetic towards him.

This highlights another significant function served by The Debrief: it leads us to growth and learning. We learn about the world: what to say, what to wear, how to react, how to read the other person, and so on. We become aware of prevailing norms, the progressive and the woefully outdated, and we get to see what the dating pool is like. Our friend’s mistakes become our lessons. Their joys give us hope. Dating can often feel like venturing into the wild, wild West. You need to know what to expect. And listening to enough Debriefs helps you create a map to orient yourself in this wildly unpredictable world.

My flatmates and I realised that we had developed this ritual only a few months after we had comfortably settled into it, and we consciously decided to nickname it The Debrief. At that time we didn’t make the connection that this term has with war, military tactics, and post-traumatic stress disorder. Now I know that bomber pilots during World War II were “briefed” with essential information before missions and upon their return, were questioned about their raids in an interrogation called the “debrief”. It’s so interesting that we identified with a term that originated in the military to describe the process of getting information from soldiers returning from a mission. An apt metaphor for modern heterosexual dating in a patriarchal world, which for women can often feel like picking through a battlefield strewn with landmines. Our Debriefs, too, were all about understanding the “enemy” a bit better and celebrating or comforting our brave sister-in-arms who had ventured into unfamiliar territory.

Around this time, about a decade after high school, I reconnected with my first-ever best friend from the fourth grade. Growing up, we had been inseparable, and she had front-row seats to my first crush, my first heartbreak, my first “proposal” from a boy who liked me, and so many other teenage firsts. And I of hers. Years later, when we met, we joked about each other’s first angsty obsessions, followed up on where those boys were now, and giggled at the embarrassing things we had said and done back then. In each other’s company we became thirteen again, with the code names for those boys slipping out as if it was second nature, giggling and laughing-crying at ourselves, interrupting with details in each other’s stories. The beauty was that we had been uploading our experiences into each other’s memory drives before we even possessed our first cell phones and laptops, because sharing came naturally to us. Because friendship is at the very heart of dating and romance.

Debriefs have also served as a vehicle for closer connection with women, turning acquaintances into close friends as we swap stories and find common ground. Many years after my younger cousin graduated from college and moved back to her hometown, she and I reconnected as adults. One evening over drinks, she gave me the most legendary Debrief that started from her high school years and covered over a decade’s worth of exciting and heartbreaking encounters with crushes, boyfriends, bullies, frenemies, and rule-breaking. Her one Debrief transformed our dynamic – she was no longer a baby sister I had to be discreet and close-lipped around, but a trusted friend I could treat as an equal. At the end of that hours-long Debrief we became girlfriends, the age gap between us fading into oblivion.

What is dating without The Debrief? Like a ship without a sail, like a bard without a tale. It’s like the famous philosophical riddle: if a girl goes on a date and no one gets to hear The Debrief, did she even really go on the date? That brings me to another vital, almost divine function served by The Debrief: preserving memory via record-keeping with others when our own hearts can blur details as they try to create comfortable narratives of our lives. Humans have a vital need to have a witness to our lives. Many of us grow up and find lifelong partners who fulfil this function for us. But until then, our friends are the witnesses who live our journeys with us, holding space for our experiences and emotions, remembering the details we would rather forget, sharpening our understanding with their analysis, serving as faithful repositories of our lives decades later.

You see The Debrief in action everywhere, but my favourite portrayal is in Sex and the City. Take literally any episode and any one of the four friends: any time any of them has an encounter with a man, a detailed Debrief to the other three follows. Whether one is getting cheated on, navigating infertility, wondering if a man is too good to be true, getting dumped via a Post-it, or reading an ex’s wedding announcement in the newspaper, her friends are there to listen sympathetically, giving lots of advice and the occasional reality check.

Any woman feeling overwhelmed or confused by her love life can thus outsource important analysis and meaning-making to her friends while counting on their varied personalities and points of view to yield a rich array of insights. I’ve done this too, on both sides of The Debrief. And when it comes to female friendships, we don’t call this emotional labour. We call it love.

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