Why It’s Important To Stress Over Your First Date Outfit

An ode to the wrinkling shirt at the back of my dresser drawer.

It's a scene many women (and men) are familiar with — staring into the abis of your closet and realizing that nothing you own seems right for this date. You’re really excited. You want to make a great first impression, look your best and feel comfortable and confident.

And then the date happens. If it sucks, that’s the end. You earmark that shirt as a potential option for the next date. If it rocks, months down the line you laugh at how much time you put into picking out an outfit (and how many options you put on and presented to your roommates for approval before going out the door).

But if the date is great and the relationship is great and months pass and you laugh and years pass… suddenly, it starts feeling sensible again.

I don’t consider myself to be a fashionable person but I tend to have a few favorite outfits. And then I tend to wear the shit out of them until they’re falling apart at the seams. Shoes tend to be the biggest casualty not surviving more than 2 years of overuse. So typically, date outfit selection had a lot to do with my standard favorites. However, as I put on dress after skirt after top, I hated everything on me. Suddenly all of my favorites looked boring and unflattering.

I was online dating again six months after breaking up with my ex. I had gone on two dates earlier in the month but neither had resulted in a second date. We were missing that spark. It was a Saturday morning in February and I was prepping for a brunch date with a classically trained musician I had been texting with for a few weeks, Mike.

I spent a lot of time getting ready for this date. Yes, I was excited, but if I’m honest it’s mostly because Olympic hockey was on and the USA and Russia were playing a REALLY exciting match. I had my laptop set up on the toilet as I straightened my hair, calling my roommate in for big plays. As the game went to shoot outs, I knew I was going to be late to this damn date (which was now inconveniently trying to take me away from this game).

On a commercial break, I threw on my makeup and then went to stare at my closet. It was snowing so a dress would be ridiculous. So I looked to the tops. After going through a few options, I picked this blue shirt with birds on it I had bought a few months back. It wasn’t particularly figure flattering but it was one of the current favs, even if the material wasn’t built to last 1,000 wears.

Oshie scored the winning goal and I was out the door, making excuses over text as I fast-walked slick Brooklyn sidewalks towards the cafe. This would not be the last time I was late for a date. I’m glad he got used to it early.

The date went great, and months passed and I laughed at my closet panic. And then Mike told me a story.

As I mentioned, it was snowing the day of our first date and he beat me to the cafe due to the hockey game. He saw me at first through the windows. He told me that he immediately thought, “I hope that’s not her.” He quickly followed up saying, “If it is, I’ll really have to step up my game not to mess this up.”

He described how he saw me, framed in the door, covered in snow, removing my hood and jacket to reveal this royal blue shirt. I saw him and waved. And as he would say, he stepped up his game.

Two years later and we’re living together. We share a dresser. I have worn the crap out of my clothes and have given many bags of clothes to charity. As I try to whittle down my cramped drawers and closet, I always pick up that damned blue shirt with the birds on it. It’s super wrinkly and never really irons out right. It’s even less figure flattering now and I really don’t wear it often.

I should give it to charity.

But I don’t think I ever can.

Staring into your closet before a date is a ridiculous thing… until that date turns into the love of your life and you’re stuck with that shirt forever.

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