It’s Our First “Real Date” And I’m Freaking Out

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I agreed to do something the other night. Something I have never done before. I don’t know how it happened, and I’m still not sure how it’s going to go down, but it has me in quite the tizzy. I’m out of my element here folks, so far out that I may need to just call off the whole thing.

This inane idea was planted just a few days ago. A fairly new suitor and I were getting drinks at a local watering hole when I naively said “What are we going to do for our third date?”

“Well we haven’t even gone on a real date yet” said Jack, the poor thing entirely unaware of the web he was weaving.

“Excuse me?” I said, slamming my vodka soda down harder than the sleepy bartender would have deemed appropriate.

“All good over here?” he said, before turning back to the game.

“Just fine” Jack laughed, as if I was a kid getting fussy at the airport.

I took a deep breath and looked the sweet boy directly in the eyes, back tracking my initial glass-slamming reaction to his ignorant comment. Draping my arms around his neck to play with the back of his hair, I smiled innocently. I may have even giggled and bit my lower lip. Hell hath no furry like a woman scorned.

The poor thing leaned in closer as if comforted by my adorable flirtations. Perched on a barstool, my suitor was standing in front of me in between my legs. I know you know the standing straddle; the way couples stand at bars when they’re in the nascent stages of courting and quite literally blind to the inconceivable notion that their PDA is utterly grotesque.

“What do you mean we’ve never been on a first date?” I laughed, as if totally unbothered by the notion that the last two dates, both of which I had planned ENTIRELY because he’s “new to the city,” had somehow been erased from our collective dating history.

I pulled him in closer, sipping my vodka soda with one hand and stroking his back with the other. I didn’t feel entirely awful about the ridiculous PDA I was employing considering the bar was dark and a total dive. It was only us, the bartender, and a guy whom I am 80% sure was my substitute teacher in the 8th grade.

“What about the first two dates we went on?” I pressed.

In the moment he took to collect his thoughts I pounced, squeezing my legs to trap him in my grasp. Now sure, he’s bigger and stronger and certainly could have wiggled out from between my legs, but between my smile turned menacing glare, hands locked around his waist, and thighs squeezed tightly around his, he knew there was no escaping my grasp. The boy had to answer for himself.

“Do you mean to say the first two dates we went on, the ones I planned, were not dates at all!?” I said in fashion so interrogative, any sit-com detective would have been proud.

“I mean, come on babe (yes he actually calls me babe – I’m on the fence with the whole thing), like a realllllll first date.”

“What are you talking about? We went to a restaurant! We had drinks! We played pool!” I said, flailing my arms in exasperation. “I planned two perfectly great dates and you know it.”

“That was drinks – not a date” he persisted.

I was actually surprised that he was not quivering in his boots; the kid wasn’t going to acquiesce just to appease me.

“I mean, I guess they were kind of dates. They were more of like a getting to know you! I want to, you know, come pick you up and open the door and take you to dinner. For god sake, I want to plan something that you know nothing about.”

I blinked at him. Trying to decide if he was simply drawing from an antiquated understanding of gender roles in dating, or if he was truly exasperated with my having high jacked the planning of the first two dates – wanting to wine and dine me a bit because, well, he liked me.

I looked at his face and smiled, and immediately I knew it was a latter. Jack wanted to take me on a “proper date,” not because he thought that’s what he should do, but because he wanted to get all dressed up and open the car door and do something without a hint of overly casual “it’s find if this doesn’t work out” drinks at the bar.

“Okay then” I said. “Take me out.”

“You can’t plan anything…” he said, waiting for my retort. “I’m picking you up at 8 on Wednesday. That’s all you can know.” He was still skeptical, I could tell.

“Wednesday at 8” I replied. “I won’t ask a thing.”

I went about my week as I do all weeks close to the holidays: with zero routine and rapidly diminishing sense of responsibility or work ethic, so when I woke up this morning I hadn’t thought that much about tonight. That is, until just now.

It’s DATE NIGHT baby, and I am freaking out.

I didn’t realize until I started thinking about it this morning that I have in fact never been on a date of this nature in my adult life. Sure in high school and college I went on a few dinner dates at the local Italian eatery, but I’ve never been on a “real date” with someone that wasn’t a boyfriend. No “guy I’m just seeing” has suggested we go all old-school on the courting process so, sitting at my desk, I’m beginning to panic. Below are a few things running through my head.

What Do I Wear?!

I’m not actually expected to put on a dress, am I? I mean, I have nothing against dresses, I’ve got some numbers in my closet I could take for a spin. That being said, what if he picks me up in like khakis and a t-shirt and I’m waltzing down my stairs in a cocktail dress? I don’t know what would be worse- my humiliation or his. So do I go casual in jeans and boots and hope we’re going somewhere trendy where jeans mean you have tech money? Or, I guess I could do a skirt! But it’s freezing and all my skirts are either too short or way too short for a nice dinner. My entire dating outfit procedure has been thrown out the window, and I know I’m going to be standing in front of my mirror at 7:45 fully naked and completely panicked.

If He’s Driving, Are We Not Drinking?

This guy is a good guy for a multitude of reasons, one being that he is exceptionally cautious of drinking and driving. He really just doesn’t do it – which is a quality I admire deeply. That being said, does that mean this is a sober date? Don’t get me wrong, I could roll with that. Living in LA I frequently rely on my sober personality when I am surrounded by Instagram models and people just generally more attractive than me. I do, however, require a little notice before going into a 3-4 hour date stone cold sober. A girl needs to emotionally prepare for that kind of mind game.

Is He Going To Drive Me Home

If you’re my mother or any other blood relative, do not read this. Seriously mom – stop. Skip to the end.

I just have some logistical questions about this whole “real date” thing. Are we going to dinner and then parting ways? Will he walk me to the front door and kiss me goodnight? The whole, “want to come back to my place?” thing doesn’t necessarily translate to the old school black and white movie I have playing in my head. So again, a girl just needs a little heads up. I’m not saying I’d want to go check out his place, but I’m also not not saying that. You know? Simply trying to manage expectations here.

Does This Mean We’re Getting Serious?

I don’t want to read too much into this thing, but what does this mean?! Our meet-up-at-a-bar dates were going splendidly! We were laughing and joking and getting to know each other well. Does this serious date mean that he likes me, like more than something casual? Do I have to start thinking about if I like him more than something casual too? Oh god. Is he going to propose?!

If I didn’t actually like this kid, I’d cancel this second. The whole situation has me all confused like a robot on the fritz, but alas, I’m not a quitter and this is just another part of the game. In fact, I think maybe this is the big leagues? Perhaps the game I’ve been playing all along is just some tee-ball version of the real deal, and I’m about to have my first night in the majors. I can’t cancel. I may strike out, but I’d rather swing and miss than never swing the bat (please god tell me I got all those sports references right).

Hopefully, all of the dating, all of the first dates and second dates and third dates at bars have prepared me for this. I mean goodness gracious, we all know I’m not new to the courting process, I’ve just never read this particular chapter. I surely don’t feel confident, but I do feel that fleeting excitement of the approaching unknown – the trepidation of an evening completely open to possibility is a comforting old friend.

I’ll keep you posted on what I wear, I’m leaning towards the dress..

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CallMeVictoria

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