The Single Woman’s Dating Playbook: The Book And The Bartender

The Single Woman's Dating Playbook: The Book And The Bartender

The Single Woman’s Dating Playbook is a compilation of successful date maneuvers that I have been strategically implementing for five years, from ages 18 – 23. To the haters that say I could have been using that brain power for other more responsible endeavors, I say clearly you have never flawlessly executed, from inception to completion, a truly magnificent first date. I live for that shit.

Please don’t misunderstand. I am certainly not in the business of fronting. In no way do I want to propagate the notion that I have anything figured out. Do I think that I am closer to 10,000 hours of first date experience than other, more relationship prone individuals? Yes. However, I certainly do not believe that makes me some sort of dating guru. I’m just a girl sharing my story, one playbook maneuver at a time.

This week, I decided to pull the curtain back farther than ever before. Maybe I’ve been listening to too much of the most transparent podcast on the internet, but I’m inclined to rip down the goddamn curtain with this one.

To be honest, I am slightly hesitant to stray from my traditional format. I know what the meat industry tycoons always say; don’t let them see how the sausage is made. Nevertheless, we’re all friends here so instead of recounting a successful conquest from the past, I will ask you to kindly hop on board the Victoria dating train and take a ride with me to ground zero, to the First Date Inception Zone™. We’re building a plan from scratch baby, buckle up.

The Background

If you weren’t aware, I’m back in the dating game after a brief vacation on commitment island. If you have any single L.A.-based friends who are funny, smart, and or attractive, let them know there’s this internet girl who you’ve never seen a picture of looking for a 2.5 boyfriend. You know, so that they can steer clear.

This weekend, you guessed it, I matched on bumble with a potential suitor. After a very rapid fire back and forth, we agreed to cut the bullshit and schedule a damn date. The whole interaction, from match to “let’s meet IRL,” clocked in at 1 hr. and 22 min. This was a good sign. I have a hard rule that no more than three hours of texting should happen before a first date.

Leo and I are meeting on Monday night at 6:00. Today is Sunday. Just now, during my obligatory pre-date personality analysis, I realized that nothing in the playbook will suit this suitor. I feel uninspired. My go-to plays, from The Surprise Linguist to The Office Break-In, are just not tickling my fancy. I’ve got an empty page in the playbook with Leo’s name all over it, so as always, let’s start with the analysis.

Determine Your Audience

Leo is artsy. He’s a writer for an architecture magazine, or something like that, and prefers breweries to tequila bars and live bands to 2000’s hip-hop. We had a few exchanges about new museums in Los Angeles and that he’s particularly fond of Kurt Vonnegut (file this fun fact away for later please).

Generally speaking, with artists, the most difficult hurdle I have to confront is their fear that we may not be compatible, considering how polar opposite our career trajectories are. A lot of times they are concerned we ultimately won’t like the same things so even if the date goes well, it never really goes anywhere.

Leo is 24 and thoughtful, I can tell by our Bumble exchanges. He thinks before he speaks and asks particularly incisive questions. What’s interesting, however, and part of the reason I’m starting from scratch with this one, is that I get the impression that Leo believes he has the upper hand. Not in a malicious way, but it’s as if he thinks he has to be gentle with me, least I find myself overwhelmed in all of his intellectual, artistic, craft beer drinking glory.

That’s fine, Leo! Little do you know, I too read books and have never met a challenge I don’t like.

Considering the above facts, I postulate that Leo likes depth in a partner and looks for intimate inquiry in conversation. He wants someone that curates a diverse understanding of art and music, one that takes seriously their own cultural edification, but doesn’t pontificate.

It’s funny, using the word pontificate makes it sound exactly like you’re pontificating, doesn’t it?

Sorry, okay, let’s get back to tricking guys into liking me.

With this analysis in mind, I know I have to plan a maneuver that highlights my laid-back side, the part of me that is interested in postmodern artists and infused liquors. I’d never fabricate interests, that’s stupid, but often I find it beneficial to pull particular parts of my personality to the forefront, as if I’m gently leading the gentleman to the conclusion he already hopes to come to; She works in business, but she’s multifaceted and has creative outlets in her life, ergo we could potentially enjoy some form of romantic involvement. I mean, they’re thinking it already, I just help them get there.

Develop The Play

Today, Leo and I were going back and forth about bar options where we could meet, I suggested my favorite dive bar right by my office. Let’s call it “Jack’s Bar.” The minute I sent the text, I got this tingling sensation. An idea started to form, slowly first, then with momentum.

To explain to you what I’m thinking, I have to take you back to last month.

Three weeks ago, I was sitting at Jack’s bar after work. It’s one of those dark, good bars. Granted, it activates after 8 o’clock but from about 5 to 7:30, there’s this sweet spot of quiet. The bartenders clean glasses and shoot the shit and I usually drink one or two martinis (up, extra dirty, Tito’s is fine), then ditch the joint before the tourists roll in.

On this particular evening, conversation was pretty dull. The staff was talking about some game, so I started reading my book. I’m on a Joan Didion kick currently. When I get on an author kick, I generally order a few books from Amazon and read them interchangeably. I’ve been doing this for years, I think it’s because I’m more interested in the voice and tone than the actual story. Also, I’m a monster, but that’s been established.

Jack, my regular bartender, started chatting to me about my book. Turns out he’s an avid reader, and immediately started waxing poetic about a Murakami novel he had just finished. He told me he reads when the bar’s quiet.

“Well here,” I said, and handed him my book. I had a stack of paperbacks waiting for me at home, so I was glad to lend him this one. I thought it’d give him something to do if his shift was slow.

Turns out, Jack loved the book. He messaged me paragraphs on Facebook about the arc of the story, Didion’s ability to make the tragic mundane, and that I was welcome to stop by and pick it up whenever I wanted. My co-workers are convinced he was just trying to sleep with me, but I don’t know, I think it’s pretty presumptuous and unhealthy to assume you can’t talk literature with a bartender without him trying to get in your pants. I don’t subscribe to that reality. Call me naive, I don’t care.

I messaged Jack that he was welcome to keep the book and that he should pass it along to a friend. Then, that was that – until, just now.

As I was thinking about Leo, I remembered our quick conversation about “The Cat’s Cradle,” a Vonnegut novel he’s particularly fond of. That’s when it hit me.


Ding, ding, motherfucking ding.

Set the Plan in Motion

I just messaged Jack on Facebook. He has confirmed he still has Slouching Towards Bethlehem, the novel I lent him, in his possession. And yes, he’s working Monday night.

Upon confirmation that he had the book, I pressed Leo on the bar location.

“So you’re okay with Jack’s bar? I go there after work a lot.”

“Good for me!!” he responded.


“See you tomorrow! Can’t wait!” I replied.

Okay, so here’s the game plan.

Tomorrow after work, I’ll put on my usual post-work date outfit in the office bathroom. I’ll make sure to arrive to the bar 10 minutes late, I can’t risk Jack giving me back the book before Leo gets there. We’ll sit down, Jack will see us and come over.

“Victoria!!” he’ll say, and pull out my book from behind the bar.

“Thank you so much, I loved her work,” Jack will say.

Jack and I will have a brief conversation about the writing style of Joan Didion, at which point I will pull another one of her novels from my purse and hand it to him.

“Give this a try,” I’ll say, before turning back to Leo to kick off our date.

“Whoa,” Leo will say under his breath, as his perceived upper hand dissipates right before our eyes. In that moment, I will have properly calibrated the playing field. This book thing, this is something Leo didn’t expect. He’ll, all of the sudden, become intrigued.

Intrigue, my friends, is the ultimate first date aphrodisiac.

Impressed with both my taste in prose and familiarity with local bartenders, I will successfully avoid the dreaded dating artists dilemma. I will have helped Leo in realizing what he already knows deep down; I’m more than just a corporate drone. I drink, I read, and I swap literature with bartenders at dive bars.

He’ll think, as he sips his Campari-based cocktail, “Did she plan this? No way…that’d be insane.”

See, I believe it only takes one moment, one presumptuous statement or one poorly timed joke, to turn a first encounter sour. Conversely, however, it only takes one unexpected twist, like a bartender returning a book to your date, to prompt the realization that maybe there is more than meets the eye. One surprising plot twist and the date goes from one-of-many to, at the very least, highly memorable. Not every playbook maneuver should be long or convoluted. Some just need to set the evening in motion by leveling the playing field or elevating the conversation, the rest, I’m sure you can handle.

So Monday night, I’m going to go out there and shoot my shot.

I’ll call this one “The Book and the Bartender.”

Wish me luck. I’ll keep you posted.

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Life is messy, let's get dirty.

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