The Single Woman’s Dating Playbook: The To-Do List

The Single Woman's Dating Playbook: The To-Do List

After a less than restful Christmas holiday, I got this strange feeling. Something was missing. I couldn’t for the life of me figure out what it was. Was it the overwhelming amount of things I have to do before I move? Was it my nervous internal monologue about how to proceed in my romantic life? Was it the lingering feeling that I misplaced a piece of pie somewhere in my room?

The strange feeling got louder (and more mysterious) until my friend and I were drinking wine on Wednesday night. He was in town for the holidays and we were discussing if it would be appropriate for him to plan a date with a woman he likes two weeks out. He didn’t want to scare her off. Upon nestling into a cocoon of down blankets and red wine, my preferred state to give unsolicited dating advice (a hovel of sorts which I have come to frequent with visceral pleasure) I realized why my life seemed so off-kilter. It has been EIGHTEEN DAYS since I cracked open the Playbook. No wonder my hovel is so full of cobwebs.

So, folks – let’s throw back the curtains, pack away our sweatpants, and get back to it. The holiday grace period is over and we’re facing 2018 square in the face. Who are you going to be this year? A doer or a watcher. A benchwarmer or a pitcher. A closer or a “let’s circle back later”-er. I don’t care if you were the king or queen of hermit city last year – last year you doesn’t even recognize this year you. 2018 you is a risk-taker, date-maker, and a put yourself out there-er.

So what if you strike out? That’s what we’re here for – a safe space you can come back to and lick your wounds. But only, ONLY if you give it your best god damn shot.

I, Victoria, your doting servant, sit here wrapped in down blankets with a fat glass of red wine on my bedside table, and present to you with the first Playbook maneuver of 2018. The To-Do List.

Plan Your Play

18 months ago, I moved back home to L.A. I graduated college in the last week of May and I started my job in the first week of June. In that time, I said goodbye to my East Coast life, packed up the remnants of my last four years, and went barreling into my first adult job. I was scattered, to say the least. I had an exorbitant amount of things to do. From finding a new apartment, doctor, and gym to organizing mountains of paperwork, I had a list as long as your average CVS receipt.

A few things took the back burner during those chaotic months, one of them being dating. That is, until I remembered life is about balance and all work and no play makes Victoria a very dull girl. Sock drawers needn’t be organized on a Saturday night.

A newly fueled desire to get back out there coupled with an ever-growing list of tasks I was dreading complicated the situation for sure. Dating takes up a lot of time.

One night, as I was on the metro texting back and forth with a boy named Brian. Brian had asked for my number the week before at a bar I frequent with my friends. No games or fuss he came up and introduced himself.

“Hi, I’m Brian,” he said, extending his hand.

“Hi Brian, I’m Victoria,” I smiled, introducing my friends as well.

“Look,” he said, “I’m new to L.A., would you want to get a drink sometime?”

I narrowed my eyes, suspicious of his forwardness. I don’t know why, but I have an instant reaction to guys that approach me out of the blue at bars. I am always afraid they have a posse of guy friends in the corner putting them up to it. I’m afraid that once I agree to a date, he’ll yell “sike!” and run back to his friends. I literally once saw this happen in middle school and I’ve been scarred ever since.

Pushing my teenage traumas aside, I turned my body more directly towards Brian in order to activate my gut instincts and get a read on the guy. I believe myself to be a good judge of character.

“Oh really, where are you from?” I asked. I swear it came off far more friendly than it sounds.

“Michigan,” he replied confidently. We chatted for another two minutes before I gave him my number. A week later we were still texting.

“I have so much to do!” I wrote.

“Me too,” he replied. “I have been putting off going to the DMV for like 3 months.”

“Haha, well I’ll go with you!” I responded.

That’s when it hit me. Why did I think being productive and dating was mutually exclusive?

Shoot Your Shot

Brian and I settled on a date for Saturday morning. We each submitted two of the most bothersome to-dos on our lists.

Brian: 1) Call and cancel hometown gym membership. 2) Take bike in for a tune-up/buy a new lock.

Victoria: 1) Find a dentist in the area that takes my insurance. 2) Return 4 pairs of jeans I ordered online to the brick and mortar store near my house.

As my alarm went off at 9 a.m. on Saturday, I rolled over in bed cursing myself for having planned such a preposterous date. I used to hate running errands with my boyfriend, why on God’s green earth would I want to do it with a stranger?

Not to mention, the pulsing hangover that was slowly starting to surface somewhere deep in my cranium was certainly making matters worse. Nevertheless, I rolled myself into the shower some 20 minutes later. There’s nothing I hate more than canceling last minute, especially with a bullshit excuse.

Day-dates are hard. What do you wear? I went with jeans and sneakers and one of those off the shoulder shirts that were in style for like 15 minutes before everyone realized they’re impossible to keep off your shoulders. At 11:02 a.m., I stood pacing outside of the bicycle shop. Honestly, I wasn’t in the finest of moods.

“Fair-warning, I’m a little bit hungover,” I had texted Brian an hour before the date.

“I too am nursing a bad one,” was his response.

Two minutes after I arrived, Brian waved from afar. He was pushing his bike with one hand and, in the other, he was carrying what looked a plastic grocery bag.

“Hi!” he said, leaning his bike against the wall. It was a nice day, clear and sunny with a light breeze. “How are you feeling?”

“Good” I laughed, giving him a hug. “What’s that?” I pointed to the bag in his hand.

“I’ll show you,” he said, leading me to a bench a few feet away. Brian pulled each item from his bag one at a time, handing me the remnants as he went. First, he pulled out two plastic cups, followed by a carton of Tropicana and a bottle of Champagne. “It’s our first step to recovery,” he smiled, watching my expression closely.

Nicely done, Brian.

We popped the champagne and spent the next 30 minutes nursing our hangovers and chatting. He told me more about his new job and I regaled him with stories of going to high school down the block. We both agreed the actual act of relocating is the worst.

After we polished off our mimosas, we took his bike inside. The entire process of dropping his bike off for a tune-up and picking out a bike lock took 30 minutes. Honestly, I didn’t even know you could send bikes in for tune-ups. While it was a task that would have felt menial alone, together it was fun. We tried on goofy helmets and checked out a bright red tandem bike.

Following the bike shop, we walked to the clothing store where I had to make my returns. In 15 minutes, I was in and out – relieved to have it off my list.

“Hey! That wasn’t so bad!” I said, impressed with our efficiency.

“Should we have mimosa number two?” Brian suggested.

15 minutes later, we sat down to brunch and occupied the two corner bar seats at a laid-back bottomless mimosa spot in Santa Monica.

“Okay, business then pleasure,” I said, taking a large gulp of my mimosa. For the next 20 minutes, I called my insurance provider to find a dentist near me and he got on the phone to cancel his gym membership in Michigan.

Suddenly, that was that. We had completed our list and, dare I say it, actually gotten to know each other in the process. We ordered a fat stack of pancakes and nestled into the end of our date where the only productive thing we had to do was get the most bang for our bottomless mimosa buck.

Brian and I proceeded to have three more dates in this exact fashion, whittling down our to-do lists one successful errand at a time. Finally, on our fourth Saturday, he sent the following texts in a row.

“The only errand I have left is to go to the grocery store.”

“But you can’t come with me.”

“Because I’m shopping for supplies to make you dinner. And for wine, to accompany said dinner.”

“But it’s silly to shop for dinner supplies unless you agree to come to dinner. So will you come to dinner tonight?”

I woke up to his barrage of texts, startled at first then immediately charmed.

“Fuck no,” I responded.

“Just kidding, I’ll be there at 8.”

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Life is messy, let's get dirty.

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