What to Wear On A First Date That Might Not Be A First Date...But Like...You Wouldn't Be Mad If It Was

Oh, the delicate art of navigating romantic ambiguity.

As a self-admitted victim of all relationship dynamics even mildly resembling When Harry Met Sally, I have found myself in one too many of these awkward grey areas. While frustrating and incredibly headache-inducing, there's a sweet spot here that can only be described as exhilarating. What will happen next? The feeling of impending plot twists is as addictive as it gets, whether it be in the realm of your career and the hundred alternate paths that swivel before you, or your love life as it dips and rights itself into whatever it is you really want, as the concert beams and beer bubbles fizzle out.

Plus, how unbelievably G R E A T does it feel after bumming it up in a beanie and giant tents of fabric all day long to then have someone prompt you to dress up and put on some high energy music as you do your hair?! Or to finally implement an eyeshadow magic trick you have needlessly perfected after watching a weirdly sizable array of YouTube tutorials?

Art by Charlie Ananas

Art by Charlie Ananas

Listen, there's no go-to beauty or style formula for this situation; I won't sit here and tell you that you're failing womankind by not trudging through the land of blisters in heels resembling miniature skyscrapers. I won't even tell you that you'd look hotter, more confident, or more eye-grabbing that way. Because that's not even an inkling of the truth. Maybe you'll match whatever preconceived notion of first-date attire your prospective company has in mind, and therefore in a roundabout way manage to tip them off to your flirty intentions. And maybe that is how you feel comfortable, which therefore allows you to channel more of your boss-ass-bitch core, but if you begrudgingly wiggle and plant yourself within a paper cut-out silhouette of "girlfriend-material," you are not doing yourself nor your crush any justice by stretching into a temporary and gilded mirage. So no. Don't assume that hair-down, eye-makeup-heavy, booty-outlined, high-heeled you is the you that you need to present.

In my own struggle-bus road trip across romantic landscapes and dead-end streets, I have found that the key to catching someone's attention is a few slight and subtle alterations in your day-to-day attire. The simple act of wearing your hair up or down in contrast to your normal routine, or wearing glasses instead of contacts for once, or going for light lipstick when you usually channel your inner goth queen—all these things are just as effective as giving in to traditional glam. The nature of visual subtly is that it is eye-catching because it is hard to pinpoint. If you typically wear all pastels, try a dark color to make your look pop. If you typically wear dresses, try pants. (What? Did I just advise that there be more pants-wearing in the world?! This will lead to shameful introspection and atonement later-on).


For those of you that aren't looking for the girl-you-fine-as-hell-no-matter-your-exterior pep talk that I so clearly feel the need to be a constant human bumper sticker for, those who are merely seeking a practical solution to an awkward problem: if you don't want to come across as too blatantly intentional in your flirtation, but only want your maybe-date to take notice, I have found that style-before-sex-appeal is the most effective middle ground. Really vamping up your sense of cool as opposed to emphasizing your lady-lumps or smoky eyes can have just as potent of an impact.

Take a patterned two-piece set for a test drive; experimenting with cool all-over prints can be a really effective way to feel like a show-stopper who also might actually be wearing pajamas (yeah, that's how comfortable the outfit is). Cool, head-turning dateable girl, meet sweet, down-to-earth homie. You might also try playing around with different chokers or layered necklaces to really punctuate the look and make yourself as externally self-assured looking as you feel internally.