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The Single Woman’s Dating Playbook, of which you already know is a compilation of my go-to first date maneuvers from ages 18-23, is meant to both be easily replicated and slightly nontraditional. If you walk away from this weekly column with even a seedling of an idea for your own first date, inspired either by my own ridiculous behavior or simply encouraged by the fact that if I can pull this shit off then you certainly can too, then I will have done my job. “My job” of course being the self-imposed, unsolicited task of recounting stories of my gallivanting around various cities with boys that would probably prefer not to be blogged about. But if Taylor Swift has taught us anything, it’s that everything is copy. Especially boys; boys are always copy.
With all of that said, this particular date that I am about to recount below may not be entirely replicable. It is more a lesson in spontaneity than anything else. But hey, if you can make it happen, email me immediately and tell me everything in fantastic detail. You know I live for this shit.
Alright, let’s get to it.
Prepare Your Play
Sometimes, no matter how hard you try, first date maneuvers are not going to go according to plan. Restaurants close early, traffic gets insane, reservations don’t get made, and lines to enter bars can be astronomically long.
You have to be flexible and think on your toes, and while nerve racking at times, that is what makes this game so god damn fun.
This particular gentleman met me at my apartment one night after work. It was a Wednesday if I remember correctly, and I had suggested we have a drink before we went to dinner. He left the planning up to me, probably because I had insisted, so I had strategically chosen a Mexican restaurant walking distance from my apartment.
Now, if you knew me, you’d know I retain very little important information. One thing I am fantastic for, however, is knowing every single BYOB restaurant in the greater Los Angeles area. When you can walk with your date to the local liquor store, pick out your liquor of choice, and bring it to dinner, you’re off to a good start. If you take nothing from the rest of this column, I beg of you, go on a BYOB date literally as soon as possible. Hell, do it tonight.
Anyways, this date was no different. I had suggested my suitor and I pick up a small (probably should have been smaller in retrospect) bottle of tequila on our way to the BYOB Mexican restaurant. The restaurant provides mixers and ice if you provide the liquor. So, according to my well laid plan, Liam and I did just that.
Oh! Oh my goodness, you guys already know about Liam and my “Just Got Home” play. Well, great. Remember when I said the date that followed my very successful execution of the Just Got Home maneuver was one of the finest bumble dates I have ever been on? This is it folks, this is the fantastically planned play that went so south, we actually ended up going south. You’ll see what I mean.
You all remember Liam, right? (If you don’t, I implore you to catch up here). He was in his thirties, a perfect balance of both mischievous and business-person responsible, and was one of the more quick-witted individuals I have met. He’s a player, too, but I wouldn’t really confirm that until months later.
Liam was funny and didn’t cut me an ounce of slack. We fired off jokes and witty retorts so fast you could have sensed the chemistry from across the room. I knew, even through our Bumble cadence, that I had to bring my A game. He was certainly going to bring his.
Shoot Your Shot (until it falls apart)
“I’m going out of town this weekend” Liam said as we walked towards the restaurant, tequila in hand.
“Oh really?” I replied, looking at him through the side of my eye. He was an unorthodox pretty, the kind you have to look at for a second before you decide he’s a stud. He looked like a man, which I liked. Plus, the strawberry blond hair and freckles from surfing weren’t the worst thing ever.
“That’s a bummer” I continued, “We’ll have to wait until next week for our second date.”
“Who says there’s a second date?” he raised one eyebrow, turning towards the restaurant.
“Oh please, Liam” I laughed.
All he did was smirk. He too knew there’d be a second date.
The smirk fell, however, when the hostess replied with the following:
“That will be about an hour” she sang, as if it was the happiest news we had heard all day. It’s fine, she was dead inside, all hostesses are.
“Oh fuck” I thought. An hour wait on a first date, even for two conversationalists on steroids like Liam and I, was going to deflate the very nice vibe we were riding.
My brain went into overdrive. We weren’t close to any other BYOB spots that I knew of, nor were there any good restaurants for at least 10 blocks. We could go back to my house, but that felt like defeat.
“Ummmm” I said, in a very un-Victoria fashion. How could I be stumped by one little set back?
That’s when, before my very eyes, Liam transformed from cool bachelor to master date saver. He tapped me out, fully prepared to out maneuver the ultimate maneuverer, and frankly I was delighted to acquiesce. It takes two to tango and I had to let him lead.
Pull An Audible
“I got this” whispered Liam, “Wait for me outside.”
I secured a table outside the restaurant, a small metal two top right in front of the door. They weren’t seating the tables outside; they generally didn’t in the evening because you can’t drink on the patio. I watched through the window as Liam slipped in between the seated patrons, weaving his way to the kitchen as if he belonged. He put a hand on a waiters arm, leaning in to whisper something I couldn’t hear.
Next thing I knew Liam was seated across from me, in his hands he had two glasses loaded with ice, a bottle of sparkling water, and half a dozen sliced limes.
“We’ll just have a drink until they seat us” he said, so casually you’d assume he didn’t know that it was illegal to drink on the street, the restaurant manager was staring directly at us with a foul grimace on his face, or that the other people in line were giving us side eye for days.
“What did you tell the waiter?” I asked, ignoring my nerves and cracking open the tequila, pouring us each a hefty serving.
“That I was on a date with a pretty girl and it was going really well” he said frankly. “It’s going well, right?”
“Yes, Liam. It’s going very well indeed.”
Over the course of the next thirty minutes the hostess only came up to us twice, insisting there was no drinking allowed on the patio. We kept assuring her it was only water, but they magically ended up seating us almost half an hour early, as if they were desperate to get us inside. Who knows, maybe that was Liam’s plan all along? We carried our drinks to the table and the date went off without a hitch. I didn’t know if we would we ever run out of things to talk about.
Once we signed the check Liam sat back in his chair, a slight smile creeping onto his face and moving to a crinkle in his eyes. I really liked the way his eyes crinkled like that.
“Hey Victoria, will you do me a favor?” he said.
“And what’s that?” I replied, maybe a little too eager. We’d made our way through a good amount of the tequila after all.
“Is there a CVS close by? I’ve got to get a few things for the trip.”
“Oh right, to North Carolina! There’s a 99-cent store up the street, that won’t work, will it?”
Liam’s eyes lit up.
“That will work perfect” he said, grabbing my hand on the way out.
Expect The Unexpected
I didn’t know why I wanted to go shopping with Liam so badly, but I did. It probably had something to do with just not wanting the date to end. We walked through the isles loading up a basket: I’d forgotten how fun 99 cent stores are!
“What are you looking for?” I asked, confused at the hodgepodge of items he had acquired. In the purple basked swinging between us he had thrown in a pack of Starbursts, one of those jumbo shot necklaces, a sleeping eye mask, a cowboy hat, two magazines, and a t-shirt that said “along for the ride” with a picture of a red convertible across the back.
“Trip supplies!” he insisted.
“Okay weirdo” I chuckled, putting the cowboy had on my head.
“You look good” he smiled.
When we checked out the cashier handed Liam a paper bag, he held it in one hand and laced my fingers through his other as we walked back to my apartment. We stood outside my building not wanting to leave.
“This was fun.” I said, shivering a bit in the cold. It was close to midnight and I knew I had to get to bed. Work in the morning was already looking like a four espresso kind of day.
Liam pushed my hair behind my ears and kissed me. He kissed me in the way that men do, confident but cognizant that a good kiss is a two way street.
“I deleted all the apps” he laughed. “I canceled all my dates, I’m so over all of the algorithms. You’re the only one I didn’t cancel.”
“Sure” I laughed. I didn’t know if it was true, but it was a nice gesture. “I’ll see you again soon?”
“Sooner than you think” he said, handing me the paper bag. “That is, if you want to do it.”
“Do what?” I asked, taking the bag in confusion. Then it clicked. The hat, the sleeping mask, the magazines…
“Come with me this weekend.”
I looked at Liam straight in the face, he had put the ball directly in my court. I could see him measuring my reaction.
“Don’t do that. Don’t tempt me; you know I’ll do it so you better be serious.”
“I say what I mean, Victoria. Are you as spontaneous as you have led me to believe?”
24 hours later I was staring out an airplane window, looking at the clouds as Liam and I prepared to land in North Carolina. And that, that is where the world’s best second date began..