Why I Would Never Dress Up On A First Date

I love dressing up. I take performative holidays like Halloween and New Year's Eve very seriously. I know how to dress for an opera. I enjoy the concept of a set of "good pearls." And even though I am the most heavily tattooed R29 editor, I feel fairly confident that I can do a pretty decent facsimile of elegant. But I have a staunch principle: I will never dress up for a first date.
(Of course, as a concept, I don't want to say "never," as I am pretty against sweeping generalizations, but it is a tenet I hold tried and true.)
In fact, when a date is approaching, I take a particularly stylized and determined approach to preparation. Or in a more succinct way, forget quirks, I just let my freak flag fly. I'll wear a leather jacket, a ripped pair of jeans, or I won't do my nails. (Or, at least, I won't freak out if they are nice and chipped.) Also, I will often make a dedicated decision to not wear a dress. Instead, I'll wear my most favorite pair of jeans or a pair of shoes that I'm always comfy in, opting for my day-to-day dress instead of something purely aspirational. Basically, I make sure that I am always wearing something that is classically "me." (In my case, this means black leather or silly pants. #Truth.)
My reasoning has less to do with being comfortable — though, admittedly, that is an element — and more to do with being comfortable with me at my least polished. Because if I can show up, chipped nails and all, and a guy is still interested in a second date, that's when I stress out a bit, do it up, and present my better (or at least "better") face.
Of course, this is not any sort of, "If you don't want me at my worst, you don't deserve me at my best" type of mentality. In fact, it is almost the opposite. In a way, it is sort of setting the bar low. Yes, I may be covered in cat hair and have a shirt with a slight coffee stain, but you know what? It is how I roll. In my head, I have convinced myself that (perhaps) this sort of nonchalance lends an air of coolness, or even mystery, that perfectly applied makeup does not. Setting a low, weird, possibly disheveled expectation means that you can only go up from there. Because, after all, you don't ever want your first date to be, say, an unrealistic representation of something you rarely attain. In fact, I don't want to start a relationship with anyone who is compatible with the "me" I put forward when I am "dressing up."
Maybe it's not a method for everyone, or even a method that is particularly effective, but it makes me feel a little better — and removes pressure from a generally stressful event. Then, in turn, I end up being a little more comfortable, laughing more, easing up on myself about my personal appearance. And then (I would like to think) the date will go smoother. The idea, of course, is that I just show up being myself. Newsflash: Sometimes that means not being 100% perfect.
So if I am running late to a date and arrive with a shoelace untied, it may all be a part of a very clever, very intentional ploy. Or it is just who I am. Either/or.
Photographed by Jens Ingvarsson and Bek Andersen