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The Jekyll and Hyde Symptoms of Choosing a First Date Outfit

This is what happens when it's just you, wine, and your closet.

You’re standing in front of your closet with nothing but your underwear on, one hand around a glass of white wine and the other balled into a fist on your hip. You’re scanning the contents of your closet, suddenly dissatisfied with everything you’ve ever owned. Taking a healthy gulp of chianti, you turn around to pace. This can mean only one thing: It’s date night.

First dates can be a lot of pressure, and the stakes only get higher the more you like the person in question. You want to dazzle and have them go home and write your initials in little hearts, and to achieve that you need to pick out something with ample amounts of wow-factor.

This is no easy feat. I mean, the pressure. Not only do you have to worry about which outfit you end up choosing but also which persona you want to indulge that night. We have many different sides to ourselves, and depending on the mood that night, someone new can come out to bat. It sounds slightly schizo, but bear with me.

A flirty mini might make you as playful as the short hemline. A laid back tunic might make you feel more relaxed and bohemian, and a fancy dress might give you a Lauren Becall, “I’ll have a pink champagne, please” type of edge. Depending on what you wear, your persona might change.

Below is the thought process we usually slip into while choosing our first date outfit, and all the different versions of ourselves we try on along the way.

Stage One: Decisions, Decisions

The Jekyll and Hyde Symptoms of Choosing a First Date Outfit

There you are, pacing in front of your closet like a general, ready to whip her recruits into shape. “We’ve only got one shot at this, ladies,” you tell your dresses, your eyes narrowed with determination. “Let’s give this everything we’ve got.”

You rifle through the sleeves, trying to determine what you feel like that night. You’re going to a dimly-lit whiskey bar, somewhere where you can leave red lipstick stains on your tumbler and lean in close to talk over the music. Feeling a non-fussy mood snake through, you reach for a sheer, flowy blouse. It’s got a touch of bohemian to it, and you feel like it would be the perfect thing to help you show you’re an easy-going, woman-of-the-world type of person. Nodding your head, you’re ready to change.

Stage Two: Everything I Own Is Garbage

Wrong, wrong. All wrong. Looking at yourself in the mirror, you give yourself a second to soak in the terrible styling you just created and then immediately whip it over your head. "Why do I even own this?!," you think, shaking your head as you throw it to the floor. Turning to your closet, you round on your once-loved friends. "Why do I own any of this?!"

Right, so we’ve had the first spiral. It’s alright. It’s just part of the process. Closing your eyes and taking a deep breath, you move on to the next step. That is, after you grab another glass of wine.

Stage Three: Maybe I Should Go Feminine?

The Jekyll and Hyde Symptoms of Choosing a First Date Outfit

So there’s something to be said about indulging in "female" things. No matter your style, a small part of you can find the unexplainable satisfaction of leaning over to the mirror to put on dark lipstick, or closing your eyes and dabbing on perfume. It brings back images of gorgeous women trapped in black and white, with silk on their shoulders and lights around them. And primping for a night out might coax that little side of you right out. So you think, why not go all-in and indulge in all the trappings? Inspired, you head back to your closet and take out your most feminine pieces. Ready to channel your inner Holly Golightly, you zip up the dress.

Stage Four: Who Even Am I?

“I look. Like a child.” You stare at your reflection in the mirror, not really understanding why you look like a six-year-old ready for Sunday mass — not Audrey Hepburn in her prime.

Nonsense. All of this is nonsense. You begin to wonder why you agreed to go out on a date anyway. Who needs this kind of stress in their lives? To think you could have been working your way through a cookie pie and watching a cancelled show on Netflix right about now. Sighing, you head back to your closet, giving yourself one more chance to pick something out before you settle on the usual cardigan and jean combo.

Stage Five: A Flutter Of Hope

The Jekyll and Hyde Symptoms of Choosing a First Date Outfit

Okay, okay, we’ve got something brewing here. You turn sideways in the mirror, smoothing down your shorts and trying to gauge how they make you feel. You decided on a high-waisted pair matched with a sleeveless turtleneck crop top, the combo making you feel both sophisticated and fun. Making you feel — you realize with a smile— just like you. You can imagine yourself sitting knee-to-knee with your date at the bar, sharing stories and making them laugh. You feel comfortable. And like yourself. You might just have a winner here.

Stage Six: A Salute To The Fallen Comrades

You turn from the mirror and are about to leave the room when you notice the destruction around you. Dresses, bras, shoes, and shorts, as far as the eye can see. Strewn across the floor, thrown onto chairs, bundled in cowering heaps next to the bed. Each one of them look so sad, and each went down with a valiant fight.

Shocked, you briefly toy with the idea of putting it all back to where it should be….

…But then you pretend you hear your phone ring and quickly leave the room. You’ll make up your mean behavior to them after the date. In the mean time, you’re ready to go charm someone’s socks off.