What 7 Days of Online Dating Taught Me about Professionalism
Work + Life Balance

What 7 Days of Online Dating Taught Me about Professionalism

by Kit Warchol
Photos Stephanie Yang | September 14, 2015


It’s 8:22 PM, and I’m lamenting the fact that I always run early. What do you do with 8 spare minutes?

I smooth my chronically unruly eyebrows, cursing whatever DNA strain (read: Dad’s) sent them my way. I check that my eyeliner hasn’t smudged, pull a face, fidget with my dopp kit, check again. Should I have gone for lipstick instead? 

So here I am, the girl who:

a) Values my independence (who cares what he thinks?)

b) Tries not to sweat the small stuff (it’s just drinks.)

c) Actually likes my Cara Delevingne (well, sort of) eyebrows

Yet somehow I’m dreading a social outing that’s supposed to be fun.

Cue my first foray into online dating, during which I’ll discover that drinks with strangers can actually lend some valuable life perspective–if you can get past the icky bits. {Click to Tweet}


At 8:27, I step into the nearly deserted bar (it’s a Tuesday and this is one of those end-of-your-Friday-night places) and spot my first date. Slumped at a table with a beer already in hand, he’s reading a book that looks oddly familiar. As my eyes adjust to the dim lighting, I wish I didn’t recognize it: Sylvia Plath’s The Bell Jar.

Five minutes later, I’m alone at the bar knowing full well I’ve been played—my date intentionally arrived early to skip picking up the tab. Plus in the brief period before I stand up to order, he’s already managed to: interrupt, insult, heckle, and forcefully assert his intelligence by evidencing his undergraduate degree in Philosophy. I’m dying inside.

Until now, I’ve spent my time as a single Angeleno far away from dating apps, meeting men organically: at friends’ barbecues, in line at coffee, and once while out for a drink (though I still can’t argue with “never meet a guy at a bar” rule). One upside of going old school is that by the time you agree to a date, you already know you’ve got rapport. Not so here.

Sure, you're stuck here for at least a round, but this is still your time. The conversation may not come easy but, for your own sake, make it bearable.

What do you do when you utterly lack chemistry with someone? How do you make conversation? 

As I blink into the backlit liquor shelves, I reach this answer: a bad date may mean you're stuck for at least a round, but this is still your time—and you’ve got a limited amount of it. The conversation may not come easy, but for your own sake, make it bearable.

I decide to treat it like I’m interviewing him for an article. I ask questions about his family, make jokes, tell stories, take mental notes on the aggravating things he says to retell later. Then miraculously, I look down to find my glass empty. Free.

I head home triumphant.

The Takeaway:

You won’t get along with everyone you meet whether it’s your boss, your sister’s new boyfriend, or a slimy client, but don’t counter with bad behavior. {Click to Tweet} We all know that excruciating moment where you find yourself face-to-face with someone you prayed you’d never see again. What if they wind up your new boss?* Suck it up, make eye contact, ask questions. Then make a graceful exit.

*If my first date winds up your boss, though, quit. 


My joining Tinder directly correlated with career frustration; the more I felt creatively unfulfilled at the office, the more I focused on booking dates. But here’s the thing: inevitably matches ask what you do.

My initial tactic was to downplay and self-deprecate, making jokes about cubicles and donut breaks. But that just made me feel terrible. After a few poor deliveries, I try a new approach: spin.

Instead of regurgitating phrases from my resume, I talk about the work I find most fulfilling even if it doesn’t pay the bills: “I write reviews for this cool magazine” (so what if it’s only freelance?);  “I’m a copywriter for that fashion brand” (so what if it’s sporadic?).

Certain tasks (like finding a new job or, I don’t know, someone who makes you happy) warrant undiverted attention.

At some point in this process, I realize it isn’t spin at all. I’ve learned to explain in simple terms who I am, what I do, and who I want to become. {Click to TweetThanks to a handful of online dates, I’ve honed my interview style and somehow backed into my personal pitch. Later, I’ll use those same explanations to land a new job.

The Takeaway:

Don’t underestimate the value of writing a personal pitch and check back in on yours often, not just when you’re going on job interviews. It centers you and keeps you honest.


I’m midway through my first week, and I’m inundated with matches. I’m skipping around between messages, dropping the ball on one conversation in my scramble to answer the next, forgetting when I’ve left someone hanging. I don’t think twice about my behavior until suddenly I realize I’m the one who’s been dropped. 

My Tinder frontrunner (we’ll call him ‘The Hudson Bay Model’) always seemed too good to be true. A successful writer with a column in a renowned style magazine, he was whip-smart, well-styled, with a penchant for heritage goods—the makings of a perfect hipster boyfriend.

We’d exchanged numbers, then a steady flow of text witticisms, then agreed to meet for drinks. And then wham—HBM abruptly stops all contact. Cold. Turkey.

“Oh, he ghosted,” a friend, also single, says as we commiserate over glasses of vinho verde, “He’s definitely online dating. You’re probably one of 30." 

Evidently “ghost” is the technical term for what I’d been doing to my other matches all week. Skin crawling, ego bruising, I’d at least found some much needed humility.   

The Takeaway:

In the modern world, we spend too much time multitasking—which is exactly how you lose perspective. {Click to Tweet} Remember to focus and prioritize. Sometimes the least obvious opportunities are also the most viable ones so consider carefully before writing them off. And certain tasks (like finding a new job or, I don’t know, someone who makes you happy) warrant undiverted attention. 


At lunch the next day, a friend catches me checking my phone and asks me what’s so important. I’m looking to see if a dude I’ve been texting has responded. He hasn’t.

“You need to learn to DGAF,” she says, taking a oddly zen sip of her iced tea. I shoot her a blank look.

“It stands for ‘Don’t Give a F**k.’ It was my dating mantra when I was single. In fact, it’s sort of my life model. You should try it.”  Lightbulb moment.

The Takeaway:

It's so easy to forget but: date are just dates, and work is just work. {Click to Tweet} The next time your coworker snaps at you or you misstep on a project? Don’t take it so personally. Apologize when necessary. Learn from the experience. Then DGAF.

Online dating gives us a hyperbolic sense of both our anonymity and the seemingly infinite opportunities. 


Throughout the week, no one actually uses the word “date.” It’s like it’s been blacklisted. 


“Let’s Hang.”

“Wanna met [sic] up tonite?” 

I’d encountered cheap Philosophy majors, Cold Turkeys, one really pleasant 10:49pm “hey so you wanna come over for a beer?” charmer (my response: Send read receipt. Delete contact.), but the closest I come to an advance plan is when a potential date and I land on a Tuesday as our tentative night for drinks.

“Finally someone normal,” I think.  

But on Sunday–midway through some back-and-forth text banter–when I ask if we’re still on, the typing bubble vanishes. Three hours later, I get:  “Sorry I was working on my carburetor” (please), then nothing else.

I try to remember when setting advanced plans was a common courtesy and not considered too much of a commitment, but I honestly can’t. These days, it’s a curveball. When someone asks you on Tuesday if you’re free Friday night? Mind-blowing and also proof positive how far we’ve regressed.

The Takeaway:

Practice the dying art of making plans in advance and keeping them. {Click to Tweet} Whether it’s a coworker catch-up or a dinner with a new friend, it’s an easy way to earn a reputation for stand-up behavior.


I’m at home after a week of messages, texts, and drinks, and I have what Urban Dictionary probably calls swipe burnout.

I’ve “ghosted” and been “ghosted.” I’ve lost sight of human decency. I’ve felt by turns excited, frustrated, charming, awkward, jaded.

Online dating gives us a hyperbolic sense of both our anonymity and seemingly infinite opportunities. {Click to Tweet} There are countless intriguing options out there–so you treat the ones you actually encounter like they’re insignificant. That Vanity Fair article got it right: this laissez-faire approach to romance is probably an omen of where society's headed. But we've all already heard those horror stories.

The point is: I was not immune. 

After repeat disappointments, I started to assume the worst of my dates from the outset, approaching them already on guard. It was a brilliant act of self-preservation. By keeping my distance and obsessively strategizing, I avoided any chance of hurt feelings. I weighed every possible outcome before committing to anything, hurled too many acerbic jokes, started calculating all my text responses and lag times. When I listened to myself on dates, I sounded tired and hollow. It made me feel gross.

Still, I behaved this way to everyone including, ultimately, someone I actually liked. Convinced he was different, I waited for him to see through my aloof exterior. Instead and not surprisingly, he took my disinterest at face value and bailed.

In seven days, I'd mastered the game and earned my membership in the Serial Daters' Club. And I hated it.

When I deleted the apps (if you must know, I tried three: Tinder, Hppn, Bumble), I felt the social claustrophobia immediately subside. I spent that Friday evening at home alone in a face mask and my ugliest underwear. My phone buzzed once: a photo of my best friend's terrier. I don't think I've ever had such a blissed out night.

The Final Takeaway

So what did I get out of the experience? Besides a prescribable case of emotional exhaustion and some anonymous 310 numbers in my text history, this thought:

What if we allowed ourselves to feel vulnerable by taking some risks personally and professionally?

Imagine if we stopped assuming bad experiences are inevitable and laid off resenting the difficult characters in our lives. When someone (whether it's that obnoxious coworker, awful date, or terrible boss) behaves badly, it's rooted in experiences we haven't shared and a background we can't fully comprehend. So why not take it less personally? Instead of trying to make sense of it all, what if we just DGAFed?

It’s probably optimistic to think that letting go would solve all our problems or make the world a better place, but it would make us slightly more empathetic. Don't assign blame when a social dynamic doesn't work—just focus on holding yourself to high standards no matter what. Keep evening plans when you'd rather go home to your Netflix queue. Take on the burden of redirecting a conversation if it becomes tense. 

When you let go, something shifts. You relax. You make everyone else feel more comfortable. It sets a different tone for the interview, meeting, date. Maybe someone you'd normally write off will surprise you simply because they appreciate that you didn't.

Then again, maybe not. But here's the thing: that's OK. You can't get along with everyone, but being a bit more gracious will still make lunch breaks and holiday parties less awkward. That counts.

P.S. Let’s put a moratorium on the term “ghosting,” shall we? 


Are you internet dating? Tell us about some of your unexpected takeaways in the comments.